Selling Intelligence (formerly Selling the Cloud)

In this episode of Selling the Cloud, Josh Payne—Founder & CEO of CoFrame and creator of GPT-Migrate—joins Mark Petruzzi and KK Anderson to explore how AI agents and continuously optimizing websites are changing the future of digital growth.

Josh shares how CoFrame is helping mid-market and enterprise companies drive 30%+ increases in conversion by building adaptive, AI-powered interfaces that test, learn, and optimize in real time. He also unpacks how his team partnered with OpenAI to create a state-of-the-art UI code generation model—and what this signals about the future of growth marketing.

Whether you’re a CMO, growth lead, or founder looking to build durable competitive advantage through AI, this episode will shift your mindset and your roadmap.

What You’ll Learn:

• From Static to Living Interfaces: Why websites are broken—and how AI agents can continuously optimize them based on real-time data and buyer behavior.
• The End of Manual A/B Testing: How Josh’s team automates experimentation at scale to unlock compound conversion lifts without traditional resource bottlenecks.
• Inside the OpenAI Partnership: How CoFrame trained a UI-specific code generation model that understands brand, layout, and style—then deployed it at scale.
• Building Competitive Advantage with AI: Why businesses that embrace continuous optimization today will outpace those stuck in manual, quarterly workflows.
• Designing the Future Growth Stack: How AI agents, data orchestration, and strategy automation will transform marketing roles and unlock new GTM velocity.

Key Topics:

• Living interfaces vs. static websites
• AI code generation for brand-consistent design
• Scaling experimentation with AI agents
• The future of CRO: conversion rate optimization
• AI in paid media, lifecycle marketing, and SEO
• Strategy design vs. manual execution
• How to evaluate AI models like Claude, Gemini, GPT-4
• Building “quant growth” systems for marketing
• Why the next big AI use case is growth engineering

Guest Spotlight: Josh Payne

Josh is the CEO of CoFrame and a repeat founder with deep roots in AI. He previously co-founded Autograph (a $2B+ unicorn), created GPT-Migrate, and authored over 20 patents and AI research papers. At CoFrame, he’s pioneering AI-first digital experiences that adapt to users in real time.

Resources & Mentions:

• CoFrame: https://coframe.com
• Article: The New Science of Growth Marketing – Every
• Tech: GPT-4 Vision, Claude, MoonDream, OpenAI fine-tuning
• Tools Mentioned: Optimizely, Adobe Target, VWO, Amplitude
• Topic: Quant growth, UI code generation, AI agents

🎧 Listen now and follow Selling the Cloud for cutting-edge conversations with the builders, strategists, and GTM leaders shaping the future of sales, growth, and AI.

Mark Petruzzi (00:02)

Welcome to today's episode of Selling the Cloud podcast. We are excited to welcome Josh Payne, founder and CEO of CoFrame. Josh is a serial entrepreneur and AI pioneer who has co-founded multiple successful companies, including Autograph, a 2 billion plus unicorn backed by A16Z and Access Bell, which has been acquired by Tata.

He's also the creator of GPT Migrate, one of the first popular coding agents and has authored over 20 papers and patents in AI. At CoFrame, Josh is building the future of digital interfaces, websites and apps that continuously optimize themselves using AI. The company recently raised 9.3 million from Coastal Ventures.

and partnered with OpenAI to develop breakthrough UI code generation technology that's driving a 30 % plus improvement in conversion rates for mid-market and enterprise clients alike. Today, Josh will share how AI agents are revolutionizing growth marketing and website optimization, what it means to build living interfaces, and how go-to-market teams should prepare for the autonomous

optimization era that we are in today. So welcome, Josh, welcome.

Josh (01:31)

Thanks so much for having me, Mark. Good to see you.

Mark Petruzzi (01:33)

Excellent. Thank you. Okay, four themes we'll focus on today. From static to living, the AI powered interface revolution, the OpenAI partnership building visually grounded AI at scale, autonomous growth, how AI agents are replacing manual optimization, and the future of marketing technology and growth engineering. So first area here, Josh, for us to jump into.

You describe CoFrame as creating living interfaces rather than static websites. What's fundamentally broken about how we think about digital experiences today?

Josh (02:15)

Yeah, so the problem with digital experiences as we know them, it comes on both sides. There's the problem from the business side, which is that it takes a lot of effort to make these digital experiences like websites or apps better for our customers. And people tend to spend a lot of money and time doing so. On the customer side, it's also an issue because you have these experiences that are one size fits all. They're not adaptive. They're not personal, you know?

They lack the context of you as a person. And the way that we're approaching this is the problem is, let's think about this from the ground up. If you could redesign the concept of digital interfaces today in a world where AI is possible and as powerful as it is, you know, look at the trend of where things are going in terms of the capabilities that it has. How would you design these customer experiences?

And that was really our impetus, which was, let's think about a world in which these digital interfaces were living in a sense, they could be adaptive and personal from the ground up. And so what we're doing essentially is, is enabling that capability for the businesses that we work with and their customer experiences, allowing their, their teams to not have to do all that grunt work and trying to continuously stay on top of.

⁓ of making those customer experiences better at great cost and ⁓ great time.

KK Anderson (03:51)

Like, what would a use case be or an example, just to go a little deeper into living interfaces? I think it sounds amazing.

Josh (03:59)

Absolutely. The biggest one that we focus on at the moment is website optimization. So you're probably very familiar with the idea of websites being a conduit for which consumers can interact and transact. And the problem with websites today is that, like I was mentioning, it takes a lot of effort to improve the conversion rate ⁓ of these sites. 95 % of

plus of traffic on the internet doesn't convert, right? It's people who go to a website and they check it out and they decided that maybe it's not a fit for them or they don't get the punchline, they don't get the idea. And this is truer in other industries than it is, know, for instance, in e-commerce, this is a huge, huge problem because the website is everything, right? And, you know, consumer finance tends to be a big one as well. And so,

What you end up seeing is ⁓ these teams spending a lot of time running experiments on these websites. You'll have a product manager or a marketer come up with a concept or an idea of what to test. They'll pass that on to a designer. They'll come up with designs and concepts. They'll then go and pass that on to an engineering team, which will go and implement the idea to be tested in the website. And that handoff process, that whole process takes weeks, sometimes months.

to do. And just an insane amount of time, when you look at the dollar value of time, an insane amount of cost and headcount. ⁓ And so it's a very broken process. It's still very beneficial and valuable, because every win that you get, every better version of that experience, tends to give you significantly more revenue, because you're stacking those conversions over time. You start to see the compounding benefits.

It's really, really painful. so the use case here that we're very focused on at CoFrame, at least, is bringing this idea of adaptive, personalized websites where different people can have different experiences that are suited to them to really help to increase that end KPI that the business cares about, usually a conversion KPI.

Mark Petruzzi (06:20)

So Josh, you have built multiple successful companies in different paradigms. What made you pivot from traditional SaaS to this AI-first approach with CoFrame?

Josh (06:35)

Yeah, I mean, this is a big question a lot of operators are facing right now, which is, how is the role of software going to evolve in this world of AI? I think we're seeing the commoditization of software. starting to see, on the flip side, we're seeing a lot of incredible new capabilities that AI is enabling. I actually think that one of the biggest opportunities right now in the space overall, in the world, is

taking processes that are manual and take a lot of work and then applying ⁓ sort of an AI first mindset to that to figure out how can we automate or optimize different parts of that process and then deliver that outcome with way less effort involved. So an example here of what we're doing, know, conversion optimization, like I was saying, that kind of takes, you know, design and engineering and product management and a bunch of different manual functions that are tedious. And so

Our approach was, can we break down that whole long process that is delivering the outcome, which is basically experiments for your website and use AI to significantly accelerate and then automate that ⁓ end to end. Now there's still human involvement for sure. And there's, there's like a gradient of, of involvement, right? But on the level of completely manual to completely automated, we're gradually moving toward that automation piece. And I think that that's.

really the biggest opportunity currently in the world of AI is looking at what is currently manual and trying to figure out systematically how can we automate that and ⁓ make it not as painful ultimately.

KK Anderson (08:17)

So really interesting. where in your professional opinion do most companies go wrong when they're trying to optimize their websites and their digital experiences? And I heard what you said earlier. And by the way, once four to eight weeks have passed and the new website is launched, that content is stale. there you are going back at it again.

Talk to me about where they go wrong and how you recommend that they shift.

Josh (08:53)

Yeah, so

I mean, a big thing that I see a lot is people are just not testing enough. know, there's that when you look at the math behind conversion optimization and experimentation, it's pretty astounding. you know, if you like, think about ⁓ a series of tests that you run, you find a couple of wins within those tests. It's not like those wins are going to give you, you know, a boost of revenue for that month and then you're done. No, that win stays with you for good, for the most part.

And they also compound over time. So if you find a 2 % conversion left here, a very small left here, you know, and then a 5 % over here, and then a 3 % over there, you suddenly have 10 % in aggregate conversion left. That could be 10 % more revenue, you know, over the course of forever. Right. And so that comp, that's why compounding is so powerful here, because you start to be able to see, you know, this like, this, this, this super linear growth.

⁓ of your business value.

Mark Petruzzi (09:56)

Yeah, what I love about that, Josh, is you're kind of taking us to continuous, instead of periodic testing. it's just, and that's the beauty of AI and it's the beauty of the intelligence that it's building in some of these large language models that, like you said, it compounds, they get better, they get smarter, and that's phenomenal. And, you know, I guess we're putting the A-B test out of

Josh (10:05)

Yes, exactly.

Mark Petruzzi (10:26)

at a commission at this point, because unless you want to look at it as A-B testing 24-7. yeah, so ⁓ what's the first thing a growth leader should understand about moving from this periodic optimization to this continuous AI-driven improvement?

Josh (10:32)

Yeah, A to Z testing.

KK Anderson (10:35)

Yeah.

Josh (10:46)

Yeah, so first thing is just like a mindset shift, right? A-B testing is valuable and it has its place. And you can still compound those wins over time with A-B testing. ⁓ We are now living in a world where the cost of creating new experiments is very low. So what I like to usually think through ⁓ when it comes to opportunities in the AI space is we talked a lot about automation, right?

like taking something that is manual and autumny. I think that's the biggest opportunity currently. ⁓ Now, there's another piece of this, which I think is also very valuable, we think of that a lot, which is what wasn't possible before that is now possible. So net new superhuman capabilities. So first is taking a human capability and then just performing that. And then the second bucket is

taking something that just wasn't possible before or feasible or reasonable to do and doing that. And so continuous optimization actually falls in that second bucket. The first bucket being here's how people are optimizing today with A-B testing. And we're just going to automate that. The second bucket is what new types of tests are now possible with AI. And I'll give you a simple example of this. ⁓

KK Anderson (11:54)

The superhuman?

Josh (12:11)

⁓ Let's see, Booking.com is actually probably one of the closest to this. They're a really, really advanced company when it comes to growth and optimization. They're running a thousand plus experiments at any given time. ⁓ But with their level of traffic, they could be running probably tens of thousands of experiments at any given time. ⁓ That's just not feasible to do ⁓ with ⁓ purely with human labor, right? It would just not make sense from an economic standpoint of time spent.

KK Anderson (12:34)

humans.

Josh (12:40)

And so yes, you'd have to cut tests off sooner. You'd probably have to use things like multi-armed bandits, advanced techniques to test lots more variants. ⁓ But in doing so, you're squeezing more value out of all that traffic that they have. And so if you can 10x your testing velocity, ⁓ that's A, not very feasible to do without the assistance of a technology like AI. But also B, it's very valuable if you can do it.

And so that's where we see this idea of continuous testing coming into play.

KK Anderson (13:16)

and that compounds over time. Yeah.

Josh (13:19)

yeah, that's the beauty

about compounding. It's like every win that you get, you know, builds on itself. And so the faster you compound, the more value your business is going to be receiving. And that's why a lot of our customers have been able to see like really big benefits very quickly with us.

KK Anderson (13:25)

Mm-hmm.

Well, and last question before we move on to the OpenAI partnership, which we're excited to learn about. So how hard is it to go from your periodic optimization or shall we say once a year optimization for some companies to this? Is it a big lift to switch? Do you have to change your whole website? What does that even entail?

Josh (13:58)

Yeah, it depends on how you're doing it. ⁓ I mean, I could speak to the co-frame piece of this, obviously. And for us, we come in and we're operational on day one with the companies that we work with. So it's no lift, basically, except for approving variations. The approval workflow still exists. And you have to make sure every variation and every experiment is given a sign off by the relevant stakeholders. for listeners at home, thinking about their own websites and how we can incorporate continuous optimization.

⁓ There ⁓ are tools out there that support this, testing tools. I think about tools like Optimizely or Adobe Target for the enterprise segment or VWO for the mid-market or lower market segments. ⁓ These are tools that we sometimes, at CoFrame, sit on top of ⁓ and we're the ones creating those tests. Really the important thing to keep in mind here is to enable continuous optimization.

It's a hungry engine. It's a very powerful engine, but it's very hungry. It requires a lot of shoveling coal in. In this case, the coal are variations. ⁓ So you have to make a lot of variations, and then those have to be based on what you're learning from the tests. And so the way that you can do this at home is by incorporating these models into how you're testing. So you're using Claude or using OpenAI, know, Chachiputti to create the variations, whether they be copy or.

or code or even images sometimes and things like that. It's not easy ⁓ to set all this up, but once you do, it's very beneficial.

KK Anderson (15:38)

Really cool. So let's go into, sorry, Mark, you go ahead. No, no. Okay. Yeah. I'm anxious to get into the OpenAI partnership. Okay. So you recently partnered with OpenAI. Congratulations. That's exciting. And you're developing what you call a first of its kind UI code, code generation. So break that down for us and tell us what this breakthrough actually means for business leaders.

Mark Petruzzi (15:39)

That sucks.

No, no kick us off. Bring us to topic topic two.

Josh (15:44)

I

Yeah, let's jump in.

Thank you.

Right, so one of the big challenges with models today is that they are very good at coding, but they're not as good at kind of like visually grounded coding. What I mean by that is when you look at a user interface, having the eye of a designer to figure out how is this code going to actually look when it's put into a user interface, especially when it comes to a pre-existing brand. So we're all operating in the world of

existing websites with existing assets and styles, and you have to stay on style and on brand and adhere to those guidelines. And a big shortcoming of today's models has been ⁓ how do we make sure that the code that we're writing when we create these variations from a layout or a user experience perspective are in adherence with these guidelines. So that was the technical challenge. ⁓ The way that we approached solving it

was we created a large data set of a bunch of different websites out there. And we trained a model to be specifically good at creating new sections of websites that were aligned with the existing brand of the existing websites. And so ⁓ our initial approach was to basically remove one of the sections and then create a text

prompt that describes what that section was in as much detail as possible, ⁓ and then use a model to create a new section that was based on that prompt. So you're basically masking out one section of the site, saying to a model, hey, look at this existing site with everything except for that section, and then create me that new section that I'm describing verbally to you. And then that's the task, and it actually creates that new section, and it's basically graded.

on how well it adheres to what the original section actually looked like. So that's the task that we use to train it. It's very similar to actually how transformers are trained in predicting the next token. But a little bit more of advanced predicting the next section instead of maybe the next token. And so that was the way that we set up the problem.

Mark Petruzzi (18:15)

Mm.

Josh (18:30)

And we were able to achieve state-of-the-art results with visually grounded cogeneration with this. And so what that means for businesses is that now, at least ones that work with CoFrame, but others maybe that would use a similar approach to train their own UI cogeneration models, ⁓ now you can have a model that really knows your brand, your visual identity, and can then create new experiences, new sections, new pages entirely, potentially. ⁓

based on what it knows about your brand. It's almost like having a designer and a front-end engineer paired up, but they've been on your team for 10 years and they know your brand really, really well.

KK Anderson (19:10)

That's really cool.

Mark Petruzzi (19:12)

So that's very cool. Josh, tell us, I guess the biggest thing that's jumping out on me is a little more of the playbook here. How did you convince OpenAI to work with you on the fine tuning of this GPT-4.0 vision? Knowing how fast they're growing, how distracted they are as an organization. So tell us a little bit about how you made that all work.

a little bit of the why. Like why are they so excited with your vision of brand consistent UI generation versus other things that may be popping around out there in the marketplace.

Josh (19:53)

Yeah, I think it comes down to just it being a really interesting problem. So in one that is interesting from a couple of different angles, one is of course the technical challenge. You know, this is a new domain ⁓ relatively, you know, like visual plus code. And so that's a really interesting combination of those two. But then there's also, it's interesting from a business standpoint, right? Like being able to create visually grounded user interfaces. That's like a really great.

⁓ thing to do. It's really core piece of this movement now, which we're seeing in like, you know, consumer products and even enterprise products that are creating, you know, code for new experiences. I think companies like Lovable and Replit and Bolt, like the ones that are just taking off right now, then ⁓ Claude and ⁓ Claude code and cursor, and there's a bunch of others too. And so

I think that that's why they were all so interested in this is because it's kind of a key piece of that equation, the front end or the user experience piece of this. How we ended up working with them is another story. had actually, I've been friends with several folks at OpenAI for a long time. ⁓ to school with a bunch of them who had joined early on and

I was at the time, I probably should have gone and done an internship there as well. I was off doing my own things usually, but it would have been probably pretty fun to be part of that early team. Anyway, I've been catching up with a bunch of them. And we were actually in the process of creating our own foundation model for UI cogeneration, right? Because this is pretty unique problem. And what we'd started to see was that ⁓

Visual ⁓ Vision Language models or VLMs were actually showing a lot of really strong promise in the open source world, ⁓ separate from the closed source models. ⁓ There was a model called Moon Dream that was out that was showing astonishingly powerful results despite it being very small. And so we were thinking, what if we made our own really strong coding LLM and then combine that with a strong vision component ⁓ using

you know, the technical term here is a clip model. And so that's that was like our initial thinking, which was if these closed source model companies like OpenAI are not going to release something that's really powerful here, ⁓ then why don't we do it ourselves? ⁓ The mistake there was, of course, thinking that they wouldn't release something as powerful. And so when I was catching up with with some of my friends there, ⁓

KK Anderson (22:39)

Yeah.

Josh (22:45)

I was mentioning this and they were like, hey, we're going to be doing something. And the moment I heard that, was like, okay, it's over. All this effort that we're putting in is going to be wasted. ⁓ You should not try to compete with these companies on that turf. ⁓ Luckily, they were, I think, impressed about how we were approaching it and asked to partner ⁓ on this. We had the data, they had the model and the team, and we kind of combined forces and did a really big sprint together for...

Mark Petruzzi (22:54)

All right.

Josh (23:14)

several weeks and got something out in time for the announcement. And then we announced it together.

KK Anderson (23:27)

That is really cool. Go ahead Mark.

Mark Petruzzi (23:31)

So, I think you have the next question, if you'd like.

KK Anderson (23:32)

So.

Okay. So now, so talk to me about kind of your go-to-market as it relates to, know, thinking about how you're going to go to market with this product. And obviously OpenAI Partnership gives you a competitive advantage. Like, you know, how defensible is it? You know, as other companies try to replicate this approach. you, do you have any competitors?

Josh (24:02)

Yeah, great question. The go-to-market approach has really been interesting because there's actually a number of different channels that we've been able to tap into. ⁓ And I know, Mark, you're actually an expert advisor at BCG, right? So you probably have seen a lot ⁓ of companies, a lot of SaaS companies approach BCG and say, hey, we'd like to work with you. BCG is actually a company that we're starting to work with as well. And that's been really beneficial.

Bain as well, we've done a little bit with. so partnerships through consulting firms have been interesting, especially on the enterprise level and looking at ways that we can bring value to these consulting firms, which are usually a little bit more, I would say hands off and sort of like advisory. But showing value quickly and getting outcomes quickly is something that is really beneficial for their model. And so that's how we've been able to partner with large consulting firms.

partnering with agencies as well, where maybe they don't have a conversion optimization practice. Maybe they're more in the paid media space or what have you, or SEO. And we can basically provide this as an added service to their offerings. ⁓ But most commonly, we're just going direct, right? We're finding people through conferences, word of mouth, customers will share and give references and stuff. ⁓ We'll have...

LinkedIn, know, campaign, not campaigns, but just like announcements of things and people will come in that way. ⁓ It's been, it's been a lot of just kind of like, you know, the momentum, keeping the momentum going and the energy in the space. think a lot of people are indeed excited about the AIs, you know, spin on it. And, the partnership with the OpenAI has actually been really helpful on the go-to-market front in terms of just like, guess, you know, credibility and they have that halo effect. so.

That's been awesome. wasn't our intention at all. It was really just let's build something cool with these folks, but ⁓ it's definitely been beneficial.

Mark Petruzzi (26:09)

that's cool, Josh. Yeah. And I've done some work with Vane over the years as well. And you're in the hands of great companies there. And it so fits into what their mission is versus what you all are doing at CoFrame as well. So let's talk about the technical challenges to orchestrating all this. What have you had to overcome in making AI generate on-brand visually consistent interfaces?

Josh (26:25)

Mm-hmm.

Mark Petruzzi (26:39)

mean, that's the key right there.

Josh (26:42)

Yeah, mean, that in itself is a technical challenge. I the models are, I have found, ⁓ they're very strong in writing code and kind of doing the quote unquote heads down work. They're actually less strong in the visual creativity side of it. They have less of a strong sense of sight than they have a sense of, I guess, logic, if you want to call it that. ⁓

That has posed a challenge, right? You know, our world is a lot about taste. It's a lot about making sure something fits in with the rest of the brand. ⁓ Conversion optimization is not simply, does this random experiment do better or not? It's about making sure that every experiment that we run is going to not only, you know, meet, but exceed the expectations of the people reviewing them on the customer side that we work with and making sure that they're actually impressed with the result before we even run the experiment.

And so that's a part of, you know, selling ourselves as Co-Frame actually. We'll go into sales calls and we will, before even working with someone, we'll show them some variations of their website. ⁓ That's kind of the beauty of the technology is that you're able to do that. Something that would otherwise take weeks of several people's time. ⁓ It's so easy for us that we can show them in a, just a qualifying call, which is kind of nice. ⁓ It's very helpful for sales.

But in order for models to be good at that, they have to be good at visuals. And most times, models off the shelves are just not good at seeing something and understanding how this is going to fit in naturally and natively with their brand. And so that was the core technical challenge here. Another challenge here ⁓ was gathering the data that was required for this. so luckily, ⁓ we were able to scrape the internet.

publicly available websites, ⁓ we basically, that's the nice part about this problem, which is that everything is basically out there for everyone to see. There's no concern ⁓ around data issues and stuff like that. But the challenge there was making a data set that actually reflected the problem that we're trying to solve, which was how do we get a model to more accurately create a new section of the site that is

aligned with the rest of website. So that was not an easy challenge to solve either. ⁓ but you luckily, when when the infrastructure is in place, you can kind of scale it up as much as you want to. And that becomes really, really powerful.

KK Anderson (29:26)

So.

Mark Petruzzi (29:26)

Great, all right, let's move, well,

we wanna move on to topic three, but I have, I keep kind of diving into one item that maybe we can do a quick sidebar in, at least in my own brain. So tell us a little more about what type of competitive advantage this creates, you know, and then how defensible is this for the companies, for your clients that jump in with you in this?

KK Anderson (29:47)

Yeah.

Josh (29:52)

Yeah, those are both great questions. we actually look at competitive advantage and defensibility a little bit in reverse. It's not what's competitive, what's like a defensible competitive advantage for a co-frame, but rather how are we creating that for our customers?

Mark Petruzzi (30:09)

Yes, and that's exactly where my question is focused on. Like how do you do that with your, how do you help your clients achieve that?

Josh (30:16)

Exactly. so that's the key piece. And I think flipping on that on its head creates this insane amount of alignment between us and our customers. ⁓ But basically with each customer, what we're doing is we're building essentially a very embedded, intelligent team member or team overall ⁓ that is working for them 24 seven. It's a team of, know, front end engineers and designers and PMs and marketers.

That's what CoFrame basically is. That is, over time as we're running more and more tests, we're learning more and more about what works for their business. And for the most part, what we've seen is, you know, what you learn about a specific business is pretty bespoke to that business. That's not the only reason why we completely silo the business data and so on. We do that also because it's just the right thing to do. you know, businesses would be concerned if we weren't doing that. But...

We certainly have found that within a given business, as this quote unquote team, embedded team gets more smart, that business has an increasing competitive advantage against other businesses that aren't 24 seven continuously optimizing and learning. You know, it's, it's, it's, it's one of those advantages. That's the beauty of compounding. We talked about earlier, but the cool part about compounding is that, you know, it might start slow, but then suddenly you have a runaway advantage. There's no way to catch up. And so.

That's what we are basically providing for our customers.

Mark Petruzzi (31:49)

Excellent, KK, will you bring us over to topic three?

KK Anderson (31:50)

Absolutely.

Yep. So let's talk about autonomous growth ⁓ and how AI agents are replacing manual optimization. And so you said that you've demonstrated 352 % improvement in click through rates with enterprise clients, which is incredible. ⁓ How should growth teams think about integrating

AI agents into their existing marketing stack.

Josh (32:21)

that's a fantastic

question. And that actually comes down to your own business. I actually have ⁓ a lot of thoughts here. marketing agents, agents in general, it's a very general topic, right? And so it's important to of like approach that from the right mindset and not just say like, here's, I'm not going to be prescriptive here because ultimately every business is different. Every workflow is different. First thing to kind of note is that

We are approaching this new world where basically ⁓ you have to make sure it impacts the bottom line. That's really, really important. ⁓ You have to make sure that it gives you an edge in whatever you're implementing agent technology into. And there is starting to become this organizational mandate as a result. The CEO of Shopify, Tobi Ludke, he recently put out a memo in which he was saying, before asking for resources, people have to demonstrate

why they can't do what they're trying to do ⁓ using AI. And so it's starting to become a mandate. So it's good that you're asking this question. The tactics that I have for evaluating whether or not to incorporate an agent into your workflow, how and when to use agents, ⁓ the first thing is to take a systems thinking mindset ⁓ to the workflow you're trying to automate here. ⁓ This is a little bit fuzzy, but

or fluffy, should say. you know, systems thinking is actually really, it's a really relevant thing to have. kind of, it's like, to me, it's this combination of AI ⁓ knowledge and knowing what the capabilities of these models are and these agents are. And then your domain knowledge, which in this case is marketing knowledge. And then finally, a general growth mindset. I know that's a fluffy term, but like having kind of that impetus to think about new ways of applying this stuff.

And so the systems thinking that comes into this is the combination of those three things. More tactically for marketing, there are several areas where this is applicable. Paid media is a big one. Looking at how ads can be, you can create different variations of ads and then optimize them over time. And there are companies that are doing this and providing ⁓ tooling for this. Coframe is going to be doing this at some point soon. ⁓ There's companies like Icon and ⁓

There's a bunch of them. Google and Meta are going to be doing themselves. There's conversion optimization for a website. That's of course what Coframe is doing. There's lifecycle marketing, emails, email campaign optimization. There's SEO, there's content operations, a bunch of stuff. The next tactic I have here is getting to know the capabilities of your AI colleagues. Trying to figure out where do we use certain models in what situations? For instance,

Claude is really great at general coding. So is now the 03 in the sort of like GPT series from OpenAI. Gemini from Google is great at long context. And so you can put a bunch of different collateral into it and have it analyze it. So my call to action for the listeners here would be get to know the different models out there and try to figure out

where are their limitations, where are their strengths. This is going to be evolving over time. So this is going to be really important to stay on top of. The next tactic I would have here is to prototype and see what's possible. You want to try to get your hands dirty and figure out what's going to show promise. ⁓ then just basically what you learn from prototyping, you should be able to have a sense for, OK, how do we apply this to my workflow and the agents that I'm trying to build?

At that point, it's really important to make sure that you're building things with what are called evals, making sure things are, you ⁓ you're actually measuring quantitatively the outcomes that you want your agent to be able to deliver. ⁓ And at the point where you do that, you know, you're in a really good place. You have a closed loop and you're ⁓ able to, with some level of reliability, automate a workflow, which is an amazing thing. And that's, think, like I was saying earlier,

the most promising part of the new AI world we're entering into.

Mark Petruzzi (36:48)

Excellent. All right, let's move us to the final topic here, and that's the future of marketing technology and growth engineering and how does this all come together for us? And the biggest question is, and this is gonna seem like I'm asking you to predict something that's 50 years in the future, because in this space, looking ahead even just 18 or 24 months is so difficult and the changes are happening daily, minute,

minute by minute. But let's say we look at 18, 24 months, how do you see the convergence of AI and growth marketing evolving? And what should marketing leaders be one, for, and secondly, driving within their companies to allow that information and those new capabilities to be executed on as quickly as possible for them?

Josh (37:42)

That's a fantastic area. You know, it's a, it's a really great question. I have this, this article, um, which I think would be a good one to check out. If you're looking to dig deeper into this topic for the listeners at home, it's on this newsletter called every by Dan shipper. Uh, it's called the new science of growth marketing. And in it, what I try to talk through is this correlation between growth marketing and finance. Interestingly enough.

So in finance, what we saw was previously, before the advent of computers and so on, people traded manually, traded stocks, bonds, other assets. And it was a very manual, very tedious process. It still is manual to an extent. People are certainly doing discretionary trading on their own. But what transformed finance in the 1980s and 90s and 2000s

⁓ was the emergence of quant finance. So quant trading and using quantitative methods, computers, ⁓ to do algorithmic trading of these assets. And what made that possible for finance was that the problem that you're trying to solve, it wasn't a simple problem, but it had a simpler output. It was either, you know, predict a price or

Mark Petruzzi (38:46)

Yeah.

Josh (39:10)

even simply a buy or sell indicator of a stock. Now the output for marketing is not something as simple as a price or a buy or sell. It is copy, is code, it is assets. ⁓ And until recently, that wasn't really possible to do with the models that we had at our disposal. But with the advent of generative AI, that is the native modality that AI is operating in.

And so what we're starting to see, and we will, I think, increasingly see, at least what I say in the article, is that just as quant finance ⁓ revolutionized the financial industry, we are going to start to see this idea of quant experimentation and quant quantitative growth methods revolutionize growth and marketing, where you'll have these strategies that are autonomous to an extent, ⁓ executed by machines.

being able to work 24 seven on your behalf and test things autonomously and make changes and personalize at a way deeper level than that was previously possible. And that's a really powerful thing because, know, to date it's been extremely tedious and time consuming to run these experiments. You require, you know, like an engineer and a designer and marketer and so on, just to get a single AB test out the door, can take weeks. What if it take minutes or hours?

you know, or less, you know, so ⁓ we're starting to enter a world where continuous optimization is then possible, all the new superhuman capabilities that we talked about earlier. ⁓ And that is what I like to think of as quant growth or quant experimentation. And I go into a bit more detail into specific strategies ⁓ in the article, very high level strategies, know, nothing super profound, but ⁓ I think it's gonna be very, very

impactful for the growth industry and for companies that use it.

KK Anderson (41:14)

So last question before we move on to our rapid fire ⁓ section. So what's going to be the highest value work for humans? Right?

Josh (41:27)

Yeah, so it's a great question.

the answer to this one, at least I kind of just borrow from this similarly borrow from what we've seen in the quant industry, right? Where instead of actually performing the trades, humans are responsible for coming up with the strategies, you know, ⁓ we have now more professionals in the financial industry than we ever have. ⁓

KK Anderson (41:46)

Okay.

Josh (41:53)

despite a lot of those manual tasks being taken by machines. ⁓ Similarly with the invention of the steam engine and electricity. ⁓ Well, the steam engine took a lot of the manual effort out of ⁓ transportation. ⁓ But we have now seen an entire new industry built up that has given a lot of jobs in performing higher level work that involves steam engines or is involved in the creation of steam engines.

There are a lot of such examples. So I think what we're going to end up seeing as applied to this industry is growth people, marketers, engineers alike, are going to have to focus less on the tedious work of writing the code, coming up with the specific assets, coming up with the specific analysis of the data and the results, and rather guiding the strategy for their businesses.

I also think we're going to see an explosion of businesses overall. We're going to, people are going to be way more empowered to be solopreneurs and, you know, small businesses and entrepreneurs and do more and offer more with less. And so we're going to start to see just like more opportunities where growth can be applied. I do think that growth teams at large, large companies might shrink because a lot of the grunt work is going to be taken on by AI. But ⁓

KK Anderson (43:00)

Yeah.

Josh (43:20)

there's going to be a lot more opportunity for many, many more types of businesses out there to use these advanced growth tactics as well.

Mark Petruzzi (43:28)

And I just want to point out that that last question that KK presented was submitted by a bot, by a robot, because they want to know how they can leverage us now into working for them instead of the other way around. it's already happening. That was not from a human. OK, we're going to go rapid fire over the last three minutes or so here. This has been great, Josh. So thank you.

KK Anderson (43:42)

Hahaha! ⁓

Josh (43:43)

already happening. wow. That's amazing.

Mark Petruzzi (43:57)

So Josh, what was the first product or service you were ever responsible for selling?

Josh (44:05)

wow. That's a great question. It has nothing to do with my current industry, but it has all to do with who I am, which is music. I had a little jazz group back in high school and we made some albums and reinvested the proceeds back into the band and made recordings, more recordings and did little touring. So yeah, that was my first exposure to business.

KK Anderson (44:14)

That's right.

Mark Petruzzi (44:28)

So everything you touch is successful, right? Is that how it works, Justin?

Josh (44:31)

Definitely not, but

I appreciate that.

KK Anderson (44:37)

Okay,

who's your favorite CEO to follow?

Josh (44:41)

man,

that's a, it's a great question. I'd have to say Eric Schmidt, ⁓ he's like next level, maybe the best operator in the whole world, ⁓ just insane story. And, ⁓ I've had the opportunity to learn some things from him directly and work with him through a couple of different things. And so, but I think he's awesome.

Mark Petruzzi (45:02)

Very cool. Okay, a tool other than CoFrame that every growth leader should be using.

Josh (45:11)

man. Well, I think it's really, really important to have a really solid sense of your data for sure. So some type of, some type of analytics platform, Amplitude's a really great one. know, Adobe analytics, ⁓ post-hoc, et cetera. I think that, you know, the more you have a sense of what's happening in your business, the more you're going to be able to improve it and measure, measure those outcomes.

KK Anderson (45:39)

Question, do you have to have one of those to be able to use CoFrame?

Josh (45:42)

No, no, we actually come with full data, you know, analytics included, but we do plug into these, these systems.

KK Anderson (45:49)

Okay, now for my favorite question. Advice that you would give your 21 year old self.

Josh (45:55)

that's a good

one. man. ⁓ Okay. So I think that what I would probably say is like, like basically hype is not the same as substance. You know, I've, I've, I've seen a lot of, a lot of hype in my career so far. ⁓ And, you know, easy come easy go. Like things will just like, there'll be bubbles, they'll collapse and there'll be things that

that what you want to be doing is basically subtracting the noise to try to find the true signal and keep this level of groundedness to try to figure out what is truly valuable here and think from first principles what is going to be durable and sustain over time. And so I'd really urge myself, I guess, to really focus on the substance.

Mark Petruzzi (46:45)

Oh, I love that, Josh. And as a, know, as a reoccurring, you know, individual who's launched different companies, been CEO of multiple companies at this point, I love to have you, I love to hear you thinking about that in those terms. Because, you know, I have a lot of friends who have done the same from, you know, different company to the next and...

they start doing it a few times at the CEO level and they start to think that's their job is to always drive that hype through the market. And even sometimes within their own organization, they think they need to have credibly positive energy in their business at all times. And that's not life as we know it. And ⁓ having that realistic approach is really impressive.

Josh, thank you so much for taking the time with us. This was great and we're excited as we go along to learn more about Code Frame and see how we can leverage that into some of the work we do with clients.

Josh (47:54)

It's been a pleasure, Mark. Thanks so much for having me, Mark and KK. Really good to see you both.

KK Anderson (47:54)

Yeah, absolutely.

Thank you, Josh.

Mark Petruzzi (48:01)

Perfect, all right. Thanks, all. Thanks, Josh. Thanks, KK. Cheers.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mike Milburn—former Chief Customer Officer at Salesforce and founding team member of Service Cloud—joins Mark Petruzzi and KK Anderson for a masterclass in aligning product and sales teams around a shared go-to-market mission.

Drawing from his 15+ years at Salesforce, Mike shares hard-won frameworks for building product roadmaps that sales can actually sell, developing trust between CROs and CPOs, and scaling alignment across growth stages. This is a blueprint for leaders who want revenue-generating product strategy—not just internal harmony.

What You’ll Learn:

• The Product–Sales Friction Point: How most teams mismanage this relationship and how to turn it into a revenue advantage.
• Revenue-Calorie Framework: Why Salesforce prioritized roadmap decisions by “calories” and how to balance innovation vs. renewals.
• V2MOM as a GTM Operating System: What the V2MOM framework taught Mike about prioritization, transparency, and shared accountability.
• From Anecdotes to Data: How to structure sales feedback into decision-ready inputs for product teams.
• Product + Sales = One Team: What world-class collaboration looks like—when sales leaders evangelize the roadmap and product leaders join customer conversations.

Key Topics:

• CRO and CPO relationship-building strategies
• Translating sales objections into roadmap investment
• The role of customer success in roadmap prioritization
• Quantifying “deal blockers” to influence product
• Running effective board conversations around product
• How “True to the Core” made Salesforce a customer-led company
• Scaling product-sales collaboration from startup to enterprise

Guest Spotlight: Mike Milburn

Mike Milburn is the former Chief Customer Officer at Salesforce and was part of the founding team of Service Cloud. Today, he serves as an advisor to multiple SaaS companies. His career centers on building GTM systems where product, sales, and customer success function as one growth engine.

Resources & Mentions:

• Framework: V2MOM – Vision, Values, Methods, Obstacles, Metrics
• Salesforce Event: “True to the Core” session at Dreamforce
• Recommended Book: Behind the Cloud by Marc Benioff
• Other Concepts: Revenue-calorie model, sales telemetry, deal blocker mapping

🎧 Listen now and follow Selling the Cloud for more insights from GTM leaders building high-growth, cross-functional teams. Subscribe wherever you get your podcasts.

Mark Petruzzi (00:03.044)

Welcome to today's episode of Selling the Cloud podcast. We're thrilled today to welcome Mike Milburn, former chief customer officer and many other things at Salesforce for I believe 17 years and current advisor to some incredible technology companies as well, many of which are connected to the Salesforce ecosystem. So 15 years at Salesforce.

during a very key time for the evolution of the firm. The transformation from true startup to enterprise giant that we all know and love today. When it comes down to it, what we'd like to cover today is a number of the frameworks that Mike has used to align product and sales team throughout his career and particularly through the Salesforce journey.

Four themes we'll explore today. The product sales friction point, why most companies get this wrong, building revenue driven product roadmaps, something Salesforce always did a really good job with, probably mostly led by Mike. Go to market execution, when product and sales team need to move as one, and scaling product sales alignment.

All right, let's jump on to topic one, the product sales friction point. Mike, you mentioned that product sales relationship is one of the most critical friction points for CROs, CEOs, and boards as well. What are the fundamental misunderstandings that typically create this tension?

Mike Milburn (01:47.64)

Thanks, Mark and KK. It's great to be here. I'm really glad that you guys are having this. I can't tell you how many times I've had this conversation in private. so having this conversation in public is just, it's a really neat thing and it's an honor to here. So congrats to that. So I guess I would just kind of like imagine the audience and I would imagine in any company that you're in.

And that kind of water cooler, or maybe you're in a car or an airplane and you're having a conversation. And if you're on the sales team, you're talking about, man, I wish I had different products or better products or some sort of anxiety around the product side. And then if you go to the other side of the aisle, imagine that same conversation, the door shuts in the product meeting and you're wondering why you can't sell it. And if you sort of put yourself into that.

mode of listening and that mode of parenting those organizations, that's a pretty frequent conversation. So I think that's the place to start, is like an acknowledgement from this virtual audience, how many of you guys have been in that position of hearing friction or anxiety from both the sales side to the product side or the product scene to the sales side.

KK Anderson (03:07.463)

So that's an excellent point. So when you arrive, let's say you arrive to a new company as a CRO and you discover, let's say that the product is difficult to sell. How do you approach that conversation with the product leadership team and with your board without just saying, hey guys, this product sucks, we can't sell it.

Mike Milburn (03:32.034)

Yeah. So I think first of all, let's start with the relationships between the CPO and the CRO. And let's start with if you're the CRO identifying the CPO as one of your critical stakeholders to your success. Obviously you're reporting into probably the COO or the CEO of the company, depending on the size and the maturity, but have you properly identified the product leader as one of the key stakeholders kind of colloquial?

Locally, I would say are they on your Christmas card list? Have you earned the right to build a relationship that allows you to send a Christmas card to the chief product officer? And so where I start that relationship is really If I'm the CRO, I want to meet the head of product. I want to understand their tenure at the company I want to understand their motivations and I want to understand the successes and failures that I've had with with my predecessors

if you're a new CRO, then there was probably somebody before you. And so what were the things that they did right? And what were the things that they did wrong? Typically where that goes is again, relationships take time to build. So we're sort of jumping into how do you build a trusted relationship with them? You're to have to deliver, but ultimately you want to give the chief product officer the, the trust that you're going to bring them.

real-time feedback from the field, you're gonna sell the products that are available, and you're gonna help bring them key insights from customers and partners on what are the things that they should be building. And we're gonna touch on that in a second, but those are really the key things, being able to sell what's available, being able to bring them trusted information about what's going on in the field, and help bring them guidance about where the market is going.

Mark Petruzzi (05:30.637)

So Mike, tell us about how you built a methodology for navigating this relationship at Salesforce. And how do you make this process kind of board ready and productive and collaborative rather than adversarial?

Mike Milburn (05:51.33)

Yeah, great question, Mark. So as a, first of all, as a backdrop, you know, I had the immense honor of being one of the guys that started Service Cloud on the founding team for Service Cloud at Salesforce. And of course, Service Cloud is now over $10 billion business inside of Salesforce. And I was there on day one when we booked the first, you know, 30 or 40K order way back in the early 2000s. So that's the framework that I'm going to use. Second is,

I think all the credit really goes to Mark and Parker, Mark Benioff and Parker Harris. They created a framework that we inherited, we modified and we enhanced. And that's what I'm going to talk about today. So the way that I think about it, Mark, is what we did in the early days of Salesforce is let's say that you had unit, I don't know, let's say you had 10 calories to burn on product.

And let's just for a moment say that all calories are equal, right? We would look at those and we would say, how many those calories are you gonna spend on new or innovation things? And how many products are you, or how many calories are you gonna spend on customer success? And so for argument's sake, let's just take 10 calories. And those calories really translate to resources or funding. But if I had 10 calories,

And I devote them all towards the front of the house or all towards sales. And that meant that I was going to create some debt on the renewal side or on the customer success side. And conversely, if I spent all 10 calories and I didn't create any new innovation, I might suffer on sales, but I would really be strong in customer success or renewals. So once you go away from the teeter totter,

And you go, well, the natural instinct is to peanut butter and to do five on each, let's say in this, in this hypothetical example. And I think what Parker really did was challenge that idea of peanut buttering and say, let's be really, really thoughtful, deliberate and challenging. And maybe you spent seven calories on sales and only three on customer success or vice versa.

Mike Milburn (08:10.134)

And let's really think about the trade-offs and let's make those data driven revenue generating success oriented decisions. And so where we took that team was we would take the product roadmap that was based off of that framework. And we would go to the sales leadership and we'd say, can you sell this? And the sales leadership would sign up to sell that. And I think, you know, that, conversation that we started with was.

can the product team create a roadmap that the sales team stands behind? And if you imagine that conversation, that's a very delicate conversation. The sales team has to take accountability for, if you're gonna go build something, then the sales team needs to be the one to stand up and say, if you build that, I'm gonna go sell it. There's always problems that come up with pricing or packaging or competition or any one of the various things that happen in the real life world, but.

The head of products job is to create a roadmap that is innovative and can support both sales and customer success, which I'm directly calling renewals, usage and adoption. So I think that was the really neat part is once we made a data driven decision, we could then look at our roadmap and say, if I remove one calories from sales, what are the sales impacts?

And what are the renewal impacts? And once you have that, the leaders of sales, success and product can all come together and they make the right decisions for the KPIs of the team. And of course that's where the CEO and the ELT come into play. But that becomes a really fun conversation when you have it, you know, when you have it laid out like that, like for this quarter or these two quarters, let's over rotate to sales. And yeah, we might create some customer success issues.

If everyone's on the same page and there's no blame game come when the, when the customers incur issues or problems, there's no finger pointing. It's we all made this decision together. And conversely, if you make a decision to go renew all your customers, then that's going to have a lot of benefits and then you might have some, some, sales friction. So it's really creating that alignment and transparency that I was really lucky to be a part of and, mature that process.

Mark Petruzzi (10:29.315)

So Mike, before we go into our next question, I'm going to open this up a little more strategically. How much did the approach that Mark drove right from the beginning of beat a mom? How much did that get into some of this? Is the methodology that you're talking about building, is it tied to beat a mom or to just kind of work in and integrate on its own along the way?

Mike Milburn (10:58.828)

Yeah, great question, Mark. So I think of the V2Mom is really a corporate operating plan. And, you know, I've got to be candid and say, think when I first joined and I was baptized in the V2Mom process, I think I wasn't quite on board with how important it was to a company. After a couple of years, I guess I would go back and restate that and say the V2Mom was one of the most important things that Salesforce has as an asset.

And it's one of the most important things that I learned. And it's one piece of advice that I've given and driven to any company that I've been lucky enough to work with is the essence of the V2Mom is a corporate operating plan that the exec team creates and they vote on together. And it decides the company's vision, values, methods, obstacles, and metrics. Essentially, what is the operating plan? And if you do it every year, then you're allowed to pivot and change at the speed of business, no matter what size company you are.

So think it's incredibly modern. The relationship between the V2Mom and the product roadmap is really simple. If the number one V2Mom is growth, and let's say growth means sales and sales is over customer success, then you should be allowed to spend more of your product calories making products that the sales team wants you to sell. If the V2Mom is customer success is number one, then

you know, voted on that by the exec team, then you might change the priorities and saying, let's spend more calories together, making products, goods and services that help renewability. So the relationship between the V2 mom, the product roadmap, the sales leadership, the success leadership is the success leadership is it's all part of the exact same formula that drives the corporate operating plan.

KK Anderson (12:56.199)

And so where like what role do you see the CEO playing out all of this kind of? Facilitating it all you know running them running the balance

Mike Milburn (13:06.606)

Yeah. So, you we were pretty lucky. We had, you know, we had the legendary Mark Benioff running on that show. And what Mark enabled us to do was he empowered us to create a forum where you're allowed to have a healthy conversation about the VT mom. And I vividly remember, I mean, so many of these meetings all kind of blur together because they were 15, 20 years ago, but I remember somebody in the company standing up and saying, I don't agree with this.

KK Anderson (13:11.558)

Yeah.

Mike Milburn (13:33.13)

Maybe the person was an individual contributor, maybe they were an influencer, but when they challenged it, was somebody in the Roman Senate saying, hey, you guys built this, I don't agree with it. And that transparency and accountability was really important. Mark drove that culture. Everyone owned the V2 Mom. Number two was you were allowed to deputize other people for your V2 Mom.

So let me make up a little hypothetical situation here. Let's say that Mark is, let's pretend that I'm the CEO, Mark's the head of sales and KK, you're the head of products. And I would say, know, is a number one priority that we sell more and everyone goes, yeah. Well, if Mark's job is the head of sales and your job is the head of product, then you inherit those priorities. And so that's where you can't be parochial or you can't be political. You've got to do the right thing.

on the V2Mom for everyone else. And it was more than a faux pas to stand up in a V2Mom meeting and be self-serving. You had to use the V2Mom as the doctrine on how you were going to operate your organization. And you were allowed to deputize other folks. Again, part of the V2Mom conversation that I didn't say earlier was it drives success in a matrix organization.

KK Anderson (15:00.006)

you

Mike Milburn (15:00.066)

There's some organizations that are more top-down, more command and control, maybe more military or more organizations. And a lot of modern organizations, you know, the CPO and the CRO might not ever report into the same person. They might be dotted lines into the CEO or they might, their peers, right? And so the V2 mom became almost navigate the V2 mom without having to go to the CEO.

KK Anderson (15:06.311)

you

Mike Milburn (15:30.124)

And when you're empowered as as a, an executive in a company to navigate that without having to go and ask permission or to have somebody navigate those rules. you tend to, you tend to come to the right decision.

KK Anderson (15:44.423)

You know, it's ironic. Mark and I are sitting here nodding our heads thinking, this is exactly what AGS needed to hear right now. Right? You know, me, every company is no matter the size, is they're navigating growth and navigating our, you know, everything. It's so important. And for the audience who's probably like Googling what is V2Mom right now, can you give an explanation of Salesforce's framework that they've made famous?

Mark Petruzzi (15:51.939)

I that guy.

Mike Milburn (15:52.11)

Thanks

Mike Milburn (15:55.841)

Really?

Mike Milburn (16:11.586)

Yep, absolutely. Okay. So it's called the V2 mom and it stands for vision values, methods, obstacles, and metrics. And so the way that I think about it is, is the vision and values or things that the exec team created and they would socialize for approval and stakeholder value with the company. So that's the first, the V2 part. The mom part is where the work gets done. The methods, obstacles, and metrics.

And so you can YouTube V2Mom. You see a lot of companies have borrowed it, but essentially there's about 10 V2Mom methods. And those could be things like say which product has a higher priority. It could mean revenue. It could mean culture. remember when, when one year when we were really going against Siebel and there was a fear that we would turn into Siebel. I think the number one method on the V2Mom was culture.

And so that trumped growth. So the M, the first M is methods. That's the kind of how, then the obstacles are what are the things that are going get in the way. And there's a one-to-one ratio between obstacles and methods. And then the measurements are how are you going to get measured on whatever method you wanted? And the, what the execs team's job was to create all the methods and then prioritize those.

And one of the really neat moments that I saw happen over and over again was a public discussion on which method is more important. And it sounds like so innocuous. It sounds so easy. But if you were to say, what's more important sales or success? That's a hard one. Cause the more you sell, the more you have to renew, the more you renew, the easier sales get and the more references you get. Which is more important, partnership growth versus

creating a brand. Geez, Salesforce has created an amazing brand. It took time to do that, which is more important. Employee success or creating a great dream force, which is more important, having a great dream force or having 10 events locally or throughout the geos. And so once you sort of create that framework to have healthy discussion, then

Mike Milburn (18:35.478)

then you kind of get everybody on the same page. So it's a corporate operating plan for the modern SaaS company.

Mark Petruzzi (18:42.711)

Yeah, and what I love about all of that, is you kind of ties me back to what you said at the beginning and that this calorie breakdown perspective that when you look at it that way, and very few companies do, right? Very few CEOs do. Most CEOs kind of come in to these QBR meetings or wherever they're addressing a team and they're like, know, sales, sales, sales, we need to grow, we need to grow.

And then they turn around and they're like, then they start talking about customer success. And they're like, well, customer success has to be perfect in this way and have to do that. But it's not. It is a zero sum game, even in a fast growing company. the process of being mature and analyzing, hey, if we want to grow a little faster,

we're going to have to do some things that are going to be a trade off on customer success. Or if we really, really need to make sure that customer success for the next couple quarters is, you know, that our retention is off the charts, then we have to slow down and accept a couple percentage points less on our growth. That doesn't happen often in companies. And I love the way you're positioning it thus far. Let's kick into topic two.

Building revenue driven product roadmaps. KK, why don't you lead us the first question there.

KK Anderson (20:11.239)

So I'm always going to start with sales because that's my passion. And so when we think about SaaS organizations and our clients, how do you ensure that sales feedback actually influences the product roadmap? That's where I think one of the greatest breakdowns is. And honestly,

It's that frontline seller who's having a lot of these conversations and the solution architects. That's the feedback that we need to go up. Right. So how do you do that?

Mike Milburn (20:45.858)

Yep.

So this is the, I'd like everybody on the podcast to kind of close your eyes and imagine this meeting. You're in a QBR, you're in your exec meeting and it's your reporting on your results for the quarter. You're getting ready for your next board meeting of any size and scope. And you're looking at, you're the CRO and you're looking at your results.

You're looking at your feature pipeline. You're looking at amount of head count and you're painting a vision for the company on where you're going to go. And what if you had a slide that, that, that said for every opportunity, here's the quantifiable problems that we're facing in the field. In other words, you know, you just kind of invoke this frontline sales and then there's,

There's RVPs and they go AVPs and by the time it gets up to the CRO, how do you get feedback? And the image that I'm trying to conjure up is, and this might sound low level, but let's start here to get to the high level. What if on every opportunity there was a way to capture objections? And it wasn't a free text field. It was a data driven format. Is it pricing? it, is it competitive? Is it a feature or function?

KK Anderson (21:48.027)

Uh-huh.

Mike Milburn (22:13.654)

And that opportunity has a dollar sign value associated to it. So if all the reps in the field were responsible for adding in all of their objections at the, at the infantry level, at the deal level, and the CRO could run a report and say, here's the number of opportunities that I'm facing where I have pricing as a problem. And here's the accumulated dollar sign that is impacted.

Or I'm facing a feature and function gap, or I'm facing a critical piece of functionality that will require &A. Whatever it is, if you can associate deal friction with the number of deals and the amount of ARR or the amount of revenue that's associated, now you're having an exact conversation. It's not emotional. You're saying I've got X number of dollars. I'm going to choose 50 million or 5 million or 5

KK Anderson (23:05.991)

Mm-hmm.

Mike Milburn (23:11.074)

beans, whatever vector you want. And here is the data behind it that is causing me friction. Then the product organization or the partner organization or any other organization, they can ask you questions about it. They can second guess the quality of the data or what some of it means, but it's really hard to have. It's really easy to have a great conversation. If you come to that meeting with, Hey guys, our second half pipeline.

or X amount of revenue. And here are the three biggest blockers we're having to make the second half of the year. We need a flex capacitor. We need more aggressive POC pricing. And we'd really like exec sponsorship on the following 10 deals because we're having a lot of competitive pressure. Now it becomes a fulfillment opportunity for the rest of exec team to rally behind you instead of that familiar pattern of

what's happening with the deals and could have, should have, would have kind of that soft squishy. If the CRO can bring concrete examples of what they need to that meeting, then you're getting this CPO on board with you to build the right things to deliver more revenue.

Mark Petruzzi (24:30.253)

really good points there, Mike. So, okay, so how do you do, know, companies are getting customer requests, customer feedback every minute of every day. How do you determine, just how do you accept that into the process? How do you get that data into your system first? And then...

What are the criteria that should help you really drive and make it affect product decisions that will move revenue versus what may make one client feel good or even what may make the company feel good? Like we may look at this and say, yeah, this is an important one. This is important. But at end of the day, if it's not going to move revenue, it's got to be in a different place in that product roadmap.

How have you done such a great job with that throughout your entire career?

Mike Milburn (25:28.664)

You try and make the process easy, Mark. You try and make it transparent and you try to remove some of the black box. First of all, you know, the, the axiom of feedback as a gift is, is not just true if you're not getting feedback, like you're doing something very, very wrong. So let's just start with the sales side. Do you have a system that can quantify from the SEs and the sales team, the blockers that are getting in the way to sell the deal?

Do you have that? That is a binary yes or no question. And then can you summarize that by segment or geo? So part of what you implied by that question is if I have a sales team that's selling an SMB in North America and an enterprise team that is selling in Europe and they're asking for things, how do you distill those two things into a criteria?

that creates action? And the simple answer is revenue. So let's just make up some, let's just make up something to talk about. Let's say your SMB team has 20 deals, each valued at $1. Right? And that's in North America, that's $20. But your EMEA team, it wants something that is $100, but there's only one deal.

And you look at everyone and let's assume that to build those two products is the same amount of calories. Cause when you get different calories, then all of a sudden you're invoking a different vector. But first of all, can you have that conversation? This is no different than having a conversation with your family about where to go on vacation. Do you go on two little vacations and for a couple of days, you'd be on one big vacation. The world's navigated that for a long time, but now all of a sudden the sales conversation is difficult with your product team.

As a CRO, can you articulate the number of deals by segment and exactly what the blockers are? Yes or no. If you do not have that mechanism in place, then I would encourage you to use a CRM like Salesforce to create those objects. And you simply, it's part of your sales operations criteria. Every deal gets a blockers or pathways and it's not a free text.

Mike Milburn (27:49.12)

It is the top lockers and you're able to, sales ops can help you navigate, and, and run those reports. So that's the first side of it. Then, then the second side of it is as an exec team, do you have the framework to be able to decide and have that conversation? I think this is where a lot of these conversations stall is the fear that you have been building the wrong things or, or are you listening in the right way? Maybe.

You know, I just said it in a very blunt way, but if you're going to get to transparency, you've got to be able to listen and then you've got to be able to make roadmap decisions based off it. So, you know, I would say, regardless of what's happened in the past from the product and sales organizations, this is your opportunity to reset. Listen to what the sales team is telling you and then build a roadmap that addresses those. And if you're not going to address it, then just like, just like we talked about earlier, say.

we're gonna make these other decisions. And if you keep seeing this deal friction, we're sympathizing with you and we're not ignoring it. On the reverse side, on the customer success side, it's anyone that's a customer needs to be able to submit the feedback into your organization to tell you what is causing them to stop or renewal. And part of the unspoken hard part here is time.

A product roadmap usually takes a year to effect, which ironically is why Salesforce's roadmap is three RR was three RR three releases a year. So if you're going to get something into the roadmap, it might take you three releases to get that through the system. So you've got to have your radar out both on the sales and server sales and success side long enough to listen and impact that roadmap. The, so that's the time vector then.

That's all systematic and programmatic. And again, you should be able to report that to the CEO. You should be able to report that to the board. Then you have the live functions. And so this is actually a really neat story, but if you were to go on YouTube and you go true to the core, one of the most profound sessions that occurred, that occurs every dream force is usually it's Parker led, but somebody on the product team gets up.

Mike Milburn (30:14.578)

And the audience can range from five to 10,000 people. And they lead a conversation of, we being authentic with our roadmap? And this is a really neat conversation because there is no sales team. There's no success team. It's just the customer and Salesforce on stage. And what Parker does a great job of it is navigating. Every customer is going to have wants and needs. Everyone's got their individual requirements, et cetera.

And those fit either in, no, we're not going to do that. It's the wrong thing for us to build. We're thinking about it or here's where it's going to be built. And over time, what I think is really neat about true to the core is it shows Salesforce commitment to listening. It shows the customer's commitment towards giving that feedback. And I don't have any data or stats on it, but I would guess that, you know,

The reason why, the reason why that's so effective is the customers feel that their voice matters. And so if you combine both those things and you have sales radar and sales intelligence telling you what is necessary to drive a sale. And then you have customer intelligence coming through and saying, what do you intend to build?

And then you have something like true to the core, it could be exec round tables, or it could be dinners or whatever mechanism the company feels comfortable. Dreamforce is a very unique opportunity. What you see there is sort of like checks and balances, sort of like the foundation of the United States, right? We've got three different, bodies that help govern the United States. You have the sales team giving you feedback, the success team giving you feedback, and then you have actual customers. You take all three of those pieces of feedback and you look at the roadmap and you should be able to say.

KK Anderson (31:51.495)

with customers.

Mike Milburn (31:56.096)

Am I building the right things together?

KK Anderson (31:59.463)

And I wonder how often what the customer says is different in fact than the others

Mike Milburn (32:06.338)

You know, it happens. mean, I remember some very contentious, true to the core sessions and you kind of have to be candid and say, is this the right thing for the company to build? mean, the more customers you get, the more the need, do the needs of the many outweigh the needs of the few or the needs of the individual. Also here is the difference between like core product and customizable. So it's one thing for customer to say, I want this turnkey.

KK Anderson (32:28.977)

Mm-hmm.

Mike Milburn (32:32.918)

It's another thing to say you could do this and here's how you would do that. My opinion is that customers want transparency. And just because a customer wants something doesn't mean they should build it, but they deserve to be, they deserve to be heard.

KK Anderson (32:47.894)

I have a question. Just real quick, Mark, if I could, you talk about the three releases a year and that's... It feels like nowadays, that's just... Everyone wants something in the moment. They want real time. They want changes faster. want... I mean, I know it's not really a part of this topic per se, but I guess it kind of is. It's product roadmap and it's more...

Mark Petruzzi (32:48.724)

You know what's in...

KK Anderson (33:15.215)

in a real time, faster environment? Like how is the speed of business changing how SaaS companies are releasing and updating?

Mike Milburn (33:27.234)

Yeah. So this is a great topic. mean, I think we pioneered three releases a day, you know, almost 20 years ago. I guess the way I think about what Salesforce did with 3RR was it gave you some ability to have certainty to what is coming next, what you believe is coming, and then what you believe is coming a little bit longer out. So you sort of know directionally what's happening and it was transparent.

The, I felt that same anxiety many times of customers like, want this today and I want it today. I think that's tempered or weathered with building in the right way, building trust, building safety, building security. Some things take more than a day or a week or a month to build. The important thing is that does the company know where, does the customer know where you stand as an organization? Are you being heard?

And are you delivering on it? So, you know, we, I personally felt after, after being so many, after being so many, ABCs, executive briefing sessions or customer sessions or dream forces that the customer's desire to have it today is that was less important than Salesforce being able to listen and being able to build the right data driven machinery.

It also worked where if a customer said, I want X and nobody had ever heard it, you could tell the customer, you know what? You're the only customer that we've ever heard that's asked for this. And that worked in our favor a lot of times too. So if you speed that up today and people want, know, just in time releases or they want a release every two days, I don't think it changes the equation too much. Can you quantify what is being necessary in order to sell more products?

Can you quantify what is being used to renew more products? And if you can deliver it on a frequency of three times a year, five times a year, once a month, once a day, that's great. But I don't think it changes the overall calculus of, you listening to your sales team? Are you listening to your success team? Are you listening to your renewals team? are you, Ergo, you listening to your customers?

Mark Petruzzi (35:49.348)

Excellent. All right, let's go to our third topic here and go to market execution and when product and sales teams move as one. Tell us a little bit about what world class looks like around product, sales, execution. And when we use that term move as one, I've heard you use that term and that's why I'm asking it.

What does it mean for product and sales to move as one?

Mike Milburn (36:19.788)

Yeah. So.

Mike Milburn (36:24.5)

One of the great parts that I remember about our internal QBRs at Salesforce was having the sales team kick off or the sales team wrap up one of my product conversations. And imagine your CRO standing up and saying, I'm not the chief product officer.

Or I'm not heading up product, but I'm excited about the roadmap and here's why I'm excited. I'm going to go sell this because I believe in it. Now, all of a sudden you're showing alignment with your, with your critical sales component. And I think a lot of the internal meetings turn into sales is the sales job. Product is the product job and everyone just kind of goes off into their silos. So it starts with that message. Does the head of sales.

Can they deliver the product roadmap? Can the head of sales demo the product? And this is something that I just find really, really unique and interesting, but I mean, I think it's still the case today that almost every executive at Salesforce is responsible for demoing their product. And there's products that it doesn't make sense and there's really technical and I'm sure we can find corner cases, but it's pretty powerful when the head of sales is able to...

KK Anderson (37:18.897)

Alright.

Mike Milburn (37:43.064)

demo in some capacity, even if it's not the world's greatest demo. So I think those two things are one and two. Three is almost no airspace between the roadmap and the sales team. We've touched on it all throughout this conversation, Mark, but you should never ever hear from any sales team. man, I wish our roadmap was different. And I think you hear a lot of that kind of in the background or hallway conversations or exit interviews or.

Maybe I'm linked in. Sometimes you hear a lot of that. And conversely, from the product team, selling is hard. And so when you involve the product team in selling and you start to see the art of selling and the science of selling, you're going to see a lot of of sympathies and a lot of energies, know, timely today. Just today, I saw.

a CRO for one of the companies I led, he left one company and went to a new company. And when you see the product team respond to that and saying, you're going to do great, John, keep going, we loved working with you. I think that's the job of a CRO is to build those relationships that maybe said a different way. If a CRO is interviewing for their next job,

Why wouldn't the chief product officer be one of their key endorse ease or endorsements? That would be a true testimony.

KK Anderson (39:12.455)

Yeah, it really would. And, you know, take the CMO, the CPO and everybody. what's your, we have recently recorded a podcast with Kathy Minter and she talked a lot about the concept of the unified CRO and having sort of one leader that is overseeing marketing, overseeing product, overseeing customer success and in that way, rather than.

know, silent. What are your thoughts around that? Some of what you just said had me thinking.

Mike Milburn (39:48.364)

Yeah, I think there's some really exciting, I think there's been some, I think there's really exciting new roles that have been created both from CEOs and CROs, you know, and I think the CRO that is just revenue generating or just sales generating, think, I mean, first of all, it's an incredible job with a lot of responsibility and a lot of accountability.

But the inputs for that are things like marketing and branding, top of the funnel, the creation of pipeline. So if we're able to understand and navigate brand and marketing, then that's almost a next generation CRO leader. Same thing with system engineering. I've seen customer success fall in there. So it really depends on kind of the company and the investors and kind of the...

Also the candidate and the kind of role behind it. mean, at Salesforce, if you look at the current organization, it would be really bad form if you were a sales leader and you couldn't articulate the product or you couldn't articulate the message. Salesforce is lucky. 25 years later, everyone's on brand, everyone's on message. They have the enablement departments to go through that. So I think part of what you're asking, KK, is like you have

You have smaller companies, medium companies, bigger companies. You have all these different sizes of companies. Then you have private equity investors. And I think this is also an important point that, you know, in the in kind of the previous model, when companies were publicly traded or that was your goal is to IPO and be publicly traded company. Who was your accountable? Who is your accountable stakeholder? Wall Street, the stock price, right?

Now with private equity, they have a different set of goals, a different set of goals and a different timeframe for that. So what is the organizational structure that's going to drive value creation? And so I think you're seeing some consolidation in some of those roles, which is really exciting.

Mark Petruzzi (41:59.556)

And Mike, think you just set up our next podcast together and I don't think we've ever brought you by me back super fast, even though we've had amazing guests along the way. But I think we have to have a discussion after this about getting you back in in the next few weeks and talking and going more deeply into that private equity, private equity and sales, private equity and how that affects strategy within.

All these companies that you work with and and we do KK myself as well Yes, we're running lower on time here, but I'd like to get into topic for scaling product sales alignment frameworks for high growth organizations and I think the the core item here is when you when you scale from early stage startup to enterprise

How does this product sales relationship need to evolve? And how do you make that work? Because we all know these early stage companies of today are going to be the sales force of 2030. So, or at least a couple of them are. Not many, but a couple. And how do you navigate in each environment to get to that full scalability?

Mike Milburn (43:24.096)

Yeah, great question, Mark. you know, with all the turnover, all the growth and all the pace and speed that the tech ecosystem is in, here's a couple pieces of guidance. if you're the CRO and there was an impromptu board meeting, could you articulate the product roadmap and give your editorial and a data-driven decision on why it's good or conversely why it's bad?

Not subjective, not your opinion, but can you give a data-driven, supportable articulation of the product roadmap that, you know, that can you articulate that? That's thing one. Thing two is, are you listening to the customers in your, again, your sales teams are spending all of their time with customers. Are you bringing the product organization

critical information about the customers buying decisions, their needs, their wants, and are you giving, are you helping another organization build the right roadmap? Number three is, have you done, here's a litmus test one. Have you done a product tour with your top customers and your CPO? Nothing will flush out a correct alignment.

or an incorrect alignment better than a dinner or lunch or breakfast with 10 customers, head of sales and the head of product. There's nowhere to go. The door shuts. They start asking questions. What about this? How does this work? Can you have you done that before? And so I think those are three things. If I had to invoke a fourth one, it would be imagine your board meeting and reverse it.

Imagine presenting to either your private equity investors or the public counsel and imagine talking about the product roadmap and your alignment with your CPO. That's, think, what your job is as CRO is to build that alignment and build that trust.

KK Anderson (45:30.449)

So when you were in the beginnings of Service Cloud and you were there with a front row seat, what, any stories come to mind around how that scale and what that experience was like?

Mike Milburn (45:40.268)

Yeah. I think I shared this earlier. The first meeting I had when I was the GM, was terrified. I thought I was responsible for innovation and I had to figure out all this stuff. I was very, very intimidated by that opportunity. Parker leaned over and he made it just real normal. goes, just listen to what they say. Just listen.

And I listened to the sales team talk about, you know, here's the size of the opportunities. Here's the data coming. Here's the telemetry coming out of sales. And then I listened to the telemetry coming out of success. And the picture that came out of that was maybe it was 80%. Right. It was let's build this to drive more sales. Let's build this to build, to help do success. And I didn't have enough calories to, to, to do everything. So then I asked for help and it was, peer group.

How would you slice this? Would you do 80, 20, 20, 80, 50, 50, 70, 30? And I navigated that success together. And eventually it was the head of sales who became incredibly supportive of my roadmap in service cloud, which led to growth. And so the head of sales became one of our biggest advocates. so I think that story, KK, kind of, you know, while it was...

very, very intimidating and I had a of anxiety going to that meeting. It's sort of, reflect on that and Parker was exactly right. If you listen to what the sales team is providing in data driven organization, then the roadmap becomes almost a fulfillment exercise of how are you going to deliver that in the shortest amount of time? And the innovation is going to come from your product and engineering organizations on how you're going to fulfill the most amount of those things in the shortest amount of time.

Mark Petruzzi (47:35.232)

Excellent. All right, let's jump into our rapid fire segment here because I can't wait to hear some of these here from your perspective. So, you you're not a CRO. know, that's not kind of not your core, even though you've done so many amazing things over your career. So I guess this question becomes, you know, when in your career have you been asked to sell and what what product or service

was the first one you've ever really got your hands around.

Mike Milburn (48:09.506)

Yeah. So I've carried a bag. Actually, Mark, I've been responsible. I've never carried a bag from an AE perspective, but I've been responsible for revenue four or five times in my career. And believe it or not, the first is going back to Salesforce. At a matrix organization, I had no salespeople reporting to me and I had all the accountability of revenue. So I had to stand up in front of Mark and team and the board and, and, and, and announce that. So.

That was really the first one. And then every company since then, I've had some relationship, either direct or indirect, with the ownership of revenue.

KK Anderson (48:50.983)

Okay, who is your favorite, let's say CEO or C-level business mentor to follow?

Mike Milburn (48:59.34)

Yeah. So I think, so first of all, I keep an internal board of directors. And for me, what my internal board and my internal mentor do is, is they allow me to be accountable to people that I value. And one of the sales leaders that was at Salesforce, that was running one third of the company for a large majority of that time was a gentleman named Dan Del Degan, affectionately known as Triple D.

And, Dan came out of Oracle and then was it hugely influential in the growth of Salesforce. Dan later on, joined Greg Buchholz, the founder and CEO of Spring CM and Dan became the president and they sold Spring to DocuSign. Dan is probably the, gentleman that I count as my chairman of my board to, to hold myself accountable, but

I think the way that he operates in his value systems, a sales oriented to the topic of this conversation, a sales oriented CEO, I count Dan the top of that list.

Mark Petruzzi (50:03.203)

Excellent. So yeah, what about a tool that every product leader, well, let's do two of them here. Since you've managed these in a dotted line way, you're responsible for this revenue, you get to see the good, bad, and the ugly, and you get to see it from a slightly different vantage point than if you were.

a CRO managing that team day to day, which I think is going to give you even better insights to these questions. So what tool would you recommend every sales leader use to ensure they are aligned with the organization? And then is it any different for a product leader, any different recommendations there as well?

Mike Milburn (50:48.578)

Yeah. So I had the, I had the opportunity to build these tools. actually the first company I left after Salesforce was Salsify and we built both of these tools natively mark. chose Salesforce for those things. as a, as a platform, on the, on the sales side, think building the data model to be able to support what is sales need. I think it makes sense to build natively on Salesforce. It's close to the opportunity. It's close to.

leads opportunities, close one, time in sales stage, all of that makes it very, very simple. On the reverse side, it's really about usage and adoption. So, you know, there's a number of enterprise tools. I don't think I'm wedded. don't have a favorite, but what I want to know as CPO is who's using the products and what does usage and adoption look like?

from a telemetry standpoint on a good customer and what does it look like on a bad customer? So I almost think about like, I want the customer's name redacted and I wanna see usage and adoption and I wanna see those trends and I wanna see what's working and what's not working. Then I wanna start asking questions. So every product has got their own internal telemetry tools.

I'm not wedded to any of them, but I really believe in usage and adoption to drive the customer success product roadmap.

KK Anderson (52:23.079)

Nice. Okay Mike, what advice would you give your 21 year old self?

Mike Milburn (52:30.95)

I would give the advice that if I could imagine the number one relationship to build, would be the relationship between sales and products and never ever have a conversation that sounded or looked parochial about. wish sales did something different. I wish services did something different. I think there's a wonderful skill of empathy. And if you're a product person and empathize how hard it is to carry a bag and you're

family's livelihood is dependent on you selling something in some frequency, and you reverse that from a sales position, understand how hard it is to ship and QA and deliver products. I think it's the empathy between sales and service, sales and product, I think is just something I wish I'd spent more time on earlier in my career.

Mark Petruzzi (53:19.649)

I mean, Mike, isn't it just the kind of the secrets of life, you know, having that that empathy in every situation and anybody you work with or coordinate with from a business or personal perspective. So I love the way you just described that. All right, let's close up on.

Let's just say this from a product manager, a product manager perspective, somebody who is the CPO taking that role for the first time. Are there any books that can give a little bit of the tricks in the trade that you've read or do you just need to get the work and write that so we all have that insight?

Mike Milburn (54:01.41)

You know, it's a great question. The one that comes to mind is actually Mark's first book. I think it was Behind the Cloud. And it just boils it down into such, from what I remember, it's been a couple of years since I read it, Mark, but it just boils it down into the raw distilling of what it takes to create a product and get people to sell it, use it, and adopt it. And, you know, in those early days, in the first five to 10 years of Salesforce,

We did so much evangelizing, so much listening, but there was so much passion behind it. And so I think that's probably a pretty good place to start.

Mark Petruzzi (54:39.615)

Excellent. Well, we have kept you a minute more than we asked so we want to keep you on schedule for your day But Mike, this is such an honor. It was so great to to dive deep into some of these subjects with you So great that I feel like we should do it again, but we'll figure that one out from here

KK Anderson (54:56.423)

Thank

Mike Milburn (54:58.36)

Sounds good, guys. We'll talk to you soon. Great to be here. Cheers. Bye-bye.

KK Anderson (55:00.313)

Thanks Mike.

Mark Petruzzi (55:00.727)

All the best.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mike Milburn—former Chief Customer Officer at Salesforce and founding team member of Service Cloud—joins Mark Petruzzi and KK Anderson for a masterclass in aligning product and sales teams around a shared go-to-market mission.

Drawing from his 15+ years at Salesforce, Mike shares hard-won frameworks for building product roadmaps that sales can actually sell, developing trust between CROs and CPOs, and scaling alignment across growth stages. This is a blueprint for leaders who want revenue-generating product strategy—not just internal harmony.

What You’ll Learn:

• The Product–Sales Friction Point: How most teams mismanage this relationship and how to turn it into a revenue advantage.
• Revenue-Calorie Framework: Why Salesforce prioritized roadmap decisions by “calories” and how to balance innovation vs. renewals.
• V2MOM as a GTM Operating System: What the V2MOM framework taught Mike about prioritization, transparency, and shared accountability.
• From Anecdotes to Data: How to structure sales feedback into decision-ready inputs for product teams.
• Product + Sales = One Team: What world-class collaboration looks like—when sales leaders evangelize the roadmap and product leaders join customer conversations.

Key Topics:

• CRO and CPO relationship-building strategies
• Translating sales objections into roadmap investment
• The role of customer success in roadmap prioritization
• Quantifying “deal blockers” to influence product
• Running effective board conversations around product
• How “True to the Core” made Salesforce a customer-led company
• Scaling product-sales collaboration from startup to enterprise

Guest Spotlight: Mike Milburn

Mike Milburn is the former Chief Customer Officer at Salesforce and was part of the founding team of Service Cloud. Today, he serves as an advisor to multiple SaaS companies. His career centers on building GTM systems where product, sales, and customer success function as one growth engine.

Resources & Mentions:

• Framework: V2MOM – Vision, Values, Methods, Obstacles, Metrics
• Salesforce Event: “True to the Core” session at Dreamforce
• Recommended Book: Behind the Cloud by Marc Benioff
• Other Concepts: Revenue-calorie model, sales telemetry, deal blocker mapping

🎧 Listen now and follow Selling the Cloud for more insights from GTM leaders building high-growth, cross-functional teams. Subscribe wherever you get your podcasts.

Mark Petruzzi (00:03.044)

Welcome to today's episode of Selling the Cloud podcast. We're thrilled today to welcome Mike Milburn, former chief customer officer and many other things at Salesforce for I believe 17 years and current advisor to some incredible technology companies as well, many of which are connected to the Salesforce ecosystem. So 15 years at Salesforce.

during a very key time for the evolution of the firm. The transformation from true startup to enterprise giant that we all know and love today. When it comes down to it, what we'd like to cover today is a number of the frameworks that Mike has used to align product and sales team throughout his career and particularly through the Salesforce journey.

Four themes we'll explore today. The product sales friction point, why most companies get this wrong, building revenue driven product roadmaps, something Salesforce always did a really good job with, probably mostly led by Mike. Go to market execution, when product and sales team need to move as one, and scaling product sales alignment.

All right, let's jump on to topic one, the product sales friction point. Mike, you mentioned that product sales relationship is one of the most critical friction points for CROs, CEOs, and boards as well. What are the fundamental misunderstandings that typically create this tension?

Mike Milburn (01:47.64)

Thanks, Mark and KK. It's great to be here. I'm really glad that you guys are having this. I can't tell you how many times I've had this conversation in private. so having this conversation in public is just, it's a really neat thing and it's an honor to here. So congrats to that. So I guess I would just kind of like imagine the audience and I would imagine in any company that you're in.

And that kind of water cooler, or maybe you're in a car or an airplane and you're having a conversation. And if you're on the sales team, you're talking about, man, I wish I had different products or better products or some sort of anxiety around the product side. And then if you go to the other side of the aisle, imagine that same conversation, the door shuts in the product meeting and you're wondering why you can't sell it. And if you sort of put yourself into that.

mode of listening and that mode of parenting those organizations, that's a pretty frequent conversation. So I think that's the place to start, is like an acknowledgement from this virtual audience, how many of you guys have been in that position of hearing friction or anxiety from both the sales side to the product side or the product scene to the sales side.

KK Anderson (03:07.463)

So that's an excellent point. So when you arrive, let's say you arrive to a new company as a CRO and you discover, let's say that the product is difficult to sell. How do you approach that conversation with the product leadership team and with your board without just saying, hey guys, this product sucks, we can't sell it.

Mike Milburn (03:32.034)

Yeah. So I think first of all, let's start with the relationships between the CPO and the CRO. And let's start with if you're the CRO identifying the CPO as one of your critical stakeholders to your success. Obviously you're reporting into probably the COO or the CEO of the company, depending on the size and the maturity, but have you properly identified the product leader as one of the key stakeholders kind of colloquial?

Locally, I would say are they on your Christmas card list? Have you earned the right to build a relationship that allows you to send a Christmas card to the chief product officer? And so where I start that relationship is really If I'm the CRO, I want to meet the head of product. I want to understand their tenure at the company I want to understand their motivations and I want to understand the successes and failures that I've had with with my predecessors

if you're a new CRO, then there was probably somebody before you. And so what were the things that they did right? And what were the things that they did wrong? Typically where that goes is again, relationships take time to build. So we're sort of jumping into how do you build a trusted relationship with them? You're to have to deliver, but ultimately you want to give the chief product officer the, the trust that you're going to bring them.

real-time feedback from the field, you're gonna sell the products that are available, and you're gonna help bring them key insights from customers and partners on what are the things that they should be building. And we're gonna touch on that in a second, but those are really the key things, being able to sell what's available, being able to bring them trusted information about what's going on in the field, and help bring them guidance about where the market is going.

Mark Petruzzi (05:30.637)

So Mike, tell us about how you built a methodology for navigating this relationship at Salesforce. And how do you make this process kind of board ready and productive and collaborative rather than adversarial?

Mike Milburn (05:51.33)

Yeah, great question, Mark. So as a, first of all, as a backdrop, you know, I had the immense honor of being one of the guys that started Service Cloud on the founding team for Service Cloud at Salesforce. And of course, Service Cloud is now over $10 billion business inside of Salesforce. And I was there on day one when we booked the first, you know, 30 or 40K order way back in the early 2000s. So that's the framework that I'm going to use. Second is,

I think all the credit really goes to Mark and Parker, Mark Benioff and Parker Harris. They created a framework that we inherited, we modified and we enhanced. And that's what I'm going to talk about today. So the way that I think about it, Mark, is what we did in the early days of Salesforce is let's say that you had unit, I don't know, let's say you had 10 calories to burn on product.

And let's just for a moment say that all calories are equal, right? We would look at those and we would say, how many those calories are you gonna spend on new or innovation things? And how many products are you, or how many calories are you gonna spend on customer success? And so for argument's sake, let's just take 10 calories. And those calories really translate to resources or funding. But if I had 10 calories,

And I devote them all towards the front of the house or all towards sales. And that meant that I was going to create some debt on the renewal side or on the customer success side. And conversely, if I spent all 10 calories and I didn't create any new innovation, I might suffer on sales, but I would really be strong in customer success or renewals. So once you go away from the teeter totter,

And you go, well, the natural instinct is to peanut butter and to do five on each, let's say in this, in this hypothetical example. And I think what Parker really did was challenge that idea of peanut buttering and say, let's be really, really thoughtful, deliberate and challenging. And maybe you spent seven calories on sales and only three on customer success or vice versa.

Mike Milburn (08:10.134)

And let's really think about the trade-offs and let's make those data driven revenue generating success oriented decisions. And so where we took that team was we would take the product roadmap that was based off of that framework. And we would go to the sales leadership and we'd say, can you sell this? And the sales leadership would sign up to sell that. And I think, you know, that, conversation that we started with was.

can the product team create a roadmap that the sales team stands behind? And if you imagine that conversation, that's a very delicate conversation. The sales team has to take accountability for, if you're gonna go build something, then the sales team needs to be the one to stand up and say, if you build that, I'm gonna go sell it. There's always problems that come up with pricing or packaging or competition or any one of the various things that happen in the real life world, but.

The head of products job is to create a roadmap that is innovative and can support both sales and customer success, which I'm directly calling renewals, usage and adoption. So I think that was the really neat part is once we made a data driven decision, we could then look at our roadmap and say, if I remove one calories from sales, what are the sales impacts?

And what are the renewal impacts? And once you have that, the leaders of sales, success and product can all come together and they make the right decisions for the KPIs of the team. And of course that's where the CEO and the ELT come into play. But that becomes a really fun conversation when you have it, you know, when you have it laid out like that, like for this quarter or these two quarters, let's over rotate to sales. And yeah, we might create some customer success issues.

If everyone's on the same page and there's no blame game come when the, when the customers incur issues or problems, there's no finger pointing. It's we all made this decision together. And conversely, if you make a decision to go renew all your customers, then that's going to have a lot of benefits and then you might have some, some, sales friction. So it's really creating that alignment and transparency that I was really lucky to be a part of and, mature that process.

Mark Petruzzi (10:29.315)

So Mike, before we go into our next question, I'm going to open this up a little more strategically. How much did the approach that Mark drove right from the beginning of beat a mom? How much did that get into some of this? Is the methodology that you're talking about building, is it tied to beat a mom or to just kind of work in and integrate on its own along the way?

Mike Milburn (10:58.828)

Yeah, great question, Mark. So I think of the V2Mom is really a corporate operating plan. And, you know, I've got to be candid and say, think when I first joined and I was baptized in the V2Mom process, I think I wasn't quite on board with how important it was to a company. After a couple of years, I guess I would go back and restate that and say the V2Mom was one of the most important things that Salesforce has as an asset.

And it's one of the most important things that I learned. And it's one piece of advice that I've given and driven to any company that I've been lucky enough to work with is the essence of the V2Mom is a corporate operating plan that the exec team creates and they vote on together. And it decides the company's vision, values, methods, obstacles, and metrics. Essentially, what is the operating plan? And if you do it every year, then you're allowed to pivot and change at the speed of business, no matter what size company you are.

So think it's incredibly modern. The relationship between the V2Mom and the product roadmap is really simple. If the number one V2Mom is growth, and let's say growth means sales and sales is over customer success, then you should be allowed to spend more of your product calories making products that the sales team wants you to sell. If the V2Mom is customer success is number one, then

you know, voted on that by the exec team, then you might change the priorities and saying, let's spend more calories together, making products, goods and services that help renewability. So the relationship between the V2 mom, the product roadmap, the sales leadership, the success leadership is the success leadership is it's all part of the exact same formula that drives the corporate operating plan.

KK Anderson (12:56.199)

And so where like what role do you see the CEO playing out all of this kind of? Facilitating it all you know running them running the balance

Mike Milburn (13:06.606)

Yeah. So, you we were pretty lucky. We had, you know, we had the legendary Mark Benioff running on that show. And what Mark enabled us to do was he empowered us to create a forum where you're allowed to have a healthy conversation about the VT mom. And I vividly remember, I mean, so many of these meetings all kind of blur together because they were 15, 20 years ago, but I remember somebody in the company standing up and saying, I don't agree with this.

KK Anderson (13:11.558)

Yeah.

Mike Milburn (13:33.13)

Maybe the person was an individual contributor, maybe they were an influencer, but when they challenged it, was somebody in the Roman Senate saying, hey, you guys built this, I don't agree with it. And that transparency and accountability was really important. Mark drove that culture. Everyone owned the V2 Mom. Number two was you were allowed to deputize other people for your V2 Mom.

So let me make up a little hypothetical situation here. Let's say that Mark is, let's pretend that I'm the CEO, Mark's the head of sales and KK, you're the head of products. And I would say, know, is a number one priority that we sell more and everyone goes, yeah. Well, if Mark's job is the head of sales and your job is the head of product, then you inherit those priorities. And so that's where you can't be parochial or you can't be political. You've got to do the right thing.

on the V2Mom for everyone else. And it was more than a faux pas to stand up in a V2Mom meeting and be self-serving. You had to use the V2Mom as the doctrine on how you were going to operate your organization. And you were allowed to deputize other folks. Again, part of the V2Mom conversation that I didn't say earlier was it drives success in a matrix organization.

KK Anderson (15:00.006)

you

Mike Milburn (15:00.066)

There's some organizations that are more top-down, more command and control, maybe more military or more organizations. And a lot of modern organizations, you know, the CPO and the CRO might not ever report into the same person. They might be dotted lines into the CEO or they might, their peers, right? And so the V2 mom became almost navigate the V2 mom without having to go to the CEO.

KK Anderson (15:06.311)

you

Mike Milburn (15:30.124)

And when you're empowered as as a, an executive in a company to navigate that without having to go and ask permission or to have somebody navigate those rules. you tend to, you tend to come to the right decision.

KK Anderson (15:44.423)

You know, it's ironic. Mark and I are sitting here nodding our heads thinking, this is exactly what AGS needed to hear right now. Right? You know, me, every company is no matter the size, is they're navigating growth and navigating our, you know, everything. It's so important. And for the audience who's probably like Googling what is V2Mom right now, can you give an explanation of Salesforce's framework that they've made famous?

Mark Petruzzi (15:51.939)

I that guy.

Mike Milburn (15:52.11)

Thanks

Mike Milburn (15:55.841)

Really?

Mike Milburn (16:11.586)

Yep, absolutely. Okay. So it's called the V2 mom and it stands for vision values, methods, obstacles, and metrics. And so the way that I think about it is, is the vision and values or things that the exec team created and they would socialize for approval and stakeholder value with the company. So that's the first, the V2 part. The mom part is where the work gets done. The methods, obstacles, and metrics.

And so you can YouTube V2Mom. You see a lot of companies have borrowed it, but essentially there's about 10 V2Mom methods. And those could be things like say which product has a higher priority. It could mean revenue. It could mean culture. remember when, when one year when we were really going against Siebel and there was a fear that we would turn into Siebel. I think the number one method on the V2Mom was culture.

And so that trumped growth. So the M, the first M is methods. That's the kind of how, then the obstacles are what are the things that are going get in the way. And there's a one-to-one ratio between obstacles and methods. And then the measurements are how are you going to get measured on whatever method you wanted? And the, what the execs team's job was to create all the methods and then prioritize those.

And one of the really neat moments that I saw happen over and over again was a public discussion on which method is more important. And it sounds like so innocuous. It sounds so easy. But if you were to say, what's more important sales or success? That's a hard one. Cause the more you sell, the more you have to renew, the more you renew, the easier sales get and the more references you get. Which is more important, partnership growth versus

creating a brand. Geez, Salesforce has created an amazing brand. It took time to do that, which is more important. Employee success or creating a great dream force, which is more important, having a great dream force or having 10 events locally or throughout the geos. And so once you sort of create that framework to have healthy discussion, then

Mike Milburn (18:35.478)

then you kind of get everybody on the same page. So it's a corporate operating plan for the modern SaaS company.

Mark Petruzzi (18:42.711)

Yeah, and what I love about all of that, is you kind of ties me back to what you said at the beginning and that this calorie breakdown perspective that when you look at it that way, and very few companies do, right? Very few CEOs do. Most CEOs kind of come in to these QBR meetings or wherever they're addressing a team and they're like, know, sales, sales, sales, we need to grow, we need to grow.

And then they turn around and they're like, then they start talking about customer success. And they're like, well, customer success has to be perfect in this way and have to do that. But it's not. It is a zero sum game, even in a fast growing company. the process of being mature and analyzing, hey, if we want to grow a little faster,

we're going to have to do some things that are going to be a trade off on customer success. Or if we really, really need to make sure that customer success for the next couple quarters is, you know, that our retention is off the charts, then we have to slow down and accept a couple percentage points less on our growth. That doesn't happen often in companies. And I love the way you're positioning it thus far. Let's kick into topic two.

Building revenue driven product roadmaps. KK, why don't you lead us the first question there.

KK Anderson (20:11.239)

So I'm always going to start with sales because that's my passion. And so when we think about SaaS organizations and our clients, how do you ensure that sales feedback actually influences the product roadmap? That's where I think one of the greatest breakdowns is. And honestly,

It's that frontline seller who's having a lot of these conversations and the solution architects. That's the feedback that we need to go up. Right. So how do you do that?

Mike Milburn (20:45.858)

Yep.

So this is the, I'd like everybody on the podcast to kind of close your eyes and imagine this meeting. You're in a QBR, you're in your exec meeting and it's your reporting on your results for the quarter. You're getting ready for your next board meeting of any size and scope. And you're looking at, you're the CRO and you're looking at your results.

You're looking at your feature pipeline. You're looking at amount of head count and you're painting a vision for the company on where you're going to go. And what if you had a slide that, that, that said for every opportunity, here's the quantifiable problems that we're facing in the field. In other words, you know, you just kind of invoke this frontline sales and then there's,

There's RVPs and they go AVPs and by the time it gets up to the CRO, how do you get feedback? And the image that I'm trying to conjure up is, and this might sound low level, but let's start here to get to the high level. What if on every opportunity there was a way to capture objections? And it wasn't a free text field. It was a data driven format. Is it pricing? it, is it competitive? Is it a feature or function?

KK Anderson (21:48.027)

Uh-huh.

Mike Milburn (22:13.654)

And that opportunity has a dollar sign value associated to it. So if all the reps in the field were responsible for adding in all of their objections at the, at the infantry level, at the deal level, and the CRO could run a report and say, here's the number of opportunities that I'm facing where I have pricing as a problem. And here's the accumulated dollar sign that is impacted.

Or I'm facing a feature and function gap, or I'm facing a critical piece of functionality that will require &A. Whatever it is, if you can associate deal friction with the number of deals and the amount of ARR or the amount of revenue that's associated, now you're having an exact conversation. It's not emotional. You're saying I've got X number of dollars. I'm going to choose 50 million or 5 million or 5

KK Anderson (23:05.991)

Mm-hmm.

Mike Milburn (23:11.074)

beans, whatever vector you want. And here is the data behind it that is causing me friction. Then the product organization or the partner organization or any other organization, they can ask you questions about it. They can second guess the quality of the data or what some of it means, but it's really hard to have. It's really easy to have a great conversation. If you come to that meeting with, Hey guys, our second half pipeline.

or X amount of revenue. And here are the three biggest blockers we're having to make the second half of the year. We need a flex capacitor. We need more aggressive POC pricing. And we'd really like exec sponsorship on the following 10 deals because we're having a lot of competitive pressure. Now it becomes a fulfillment opportunity for the rest of exec team to rally behind you instead of that familiar pattern of

what's happening with the deals and could have, should have, would have kind of that soft squishy. If the CRO can bring concrete examples of what they need to that meeting, then you're getting this CPO on board with you to build the right things to deliver more revenue.

Mark Petruzzi (24:30.253)

really good points there, Mike. So, okay, so how do you do, know, companies are getting customer requests, customer feedback every minute of every day. How do you determine, just how do you accept that into the process? How do you get that data into your system first? And then...

What are the criteria that should help you really drive and make it affect product decisions that will move revenue versus what may make one client feel good or even what may make the company feel good? Like we may look at this and say, yeah, this is an important one. This is important. But at end of the day, if it's not going to move revenue, it's got to be in a different place in that product roadmap.

How have you done such a great job with that throughout your entire career?

Mike Milburn (25:28.664)

You try and make the process easy, Mark. You try and make it transparent and you try to remove some of the black box. First of all, you know, the, the axiom of feedback as a gift is, is not just true if you're not getting feedback, like you're doing something very, very wrong. So let's just start with the sales side. Do you have a system that can quantify from the SEs and the sales team, the blockers that are getting in the way to sell the deal?

Do you have that? That is a binary yes or no question. And then can you summarize that by segment or geo? So part of what you implied by that question is if I have a sales team that's selling an SMB in North America and an enterprise team that is selling in Europe and they're asking for things, how do you distill those two things into a criteria?

that creates action? And the simple answer is revenue. So let's just make up some, let's just make up something to talk about. Let's say your SMB team has 20 deals, each valued at $1. Right? And that's in North America, that's $20. But your EMEA team, it wants something that is $100, but there's only one deal.

And you look at everyone and let's assume that to build those two products is the same amount of calories. Cause when you get different calories, then all of a sudden you're invoking a different vector. But first of all, can you have that conversation? This is no different than having a conversation with your family about where to go on vacation. Do you go on two little vacations and for a couple of days, you'd be on one big vacation. The world's navigated that for a long time, but now all of a sudden the sales conversation is difficult with your product team.

As a CRO, can you articulate the number of deals by segment and exactly what the blockers are? Yes or no. If you do not have that mechanism in place, then I would encourage you to use a CRM like Salesforce to create those objects. And you simply, it's part of your sales operations criteria. Every deal gets a blockers or pathways and it's not a free text.

Mike Milburn (27:49.12)

It is the top lockers and you're able to, sales ops can help you navigate, and, and run those reports. So that's the first side of it. Then, then the second side of it is as an exec team, do you have the framework to be able to decide and have that conversation? I think this is where a lot of these conversations stall is the fear that you have been building the wrong things or, or are you listening in the right way? Maybe.

You know, I just said it in a very blunt way, but if you're going to get to transparency, you've got to be able to listen and then you've got to be able to make roadmap decisions based off it. So, you know, I would say, regardless of what's happened in the past from the product and sales organizations, this is your opportunity to reset. Listen to what the sales team is telling you and then build a roadmap that addresses those. And if you're not going to address it, then just like, just like we talked about earlier, say.

we're gonna make these other decisions. And if you keep seeing this deal friction, we're sympathizing with you and we're not ignoring it. On the reverse side, on the customer success side, it's anyone that's a customer needs to be able to submit the feedback into your organization to tell you what is causing them to stop or renewal. And part of the unspoken hard part here is time.

A product roadmap usually takes a year to effect, which ironically is why Salesforce's roadmap is three RR was three RR three releases a year. So if you're going to get something into the roadmap, it might take you three releases to get that through the system. So you've got to have your radar out both on the sales and server sales and success side long enough to listen and impact that roadmap. The, so that's the time vector then.

That's all systematic and programmatic. And again, you should be able to report that to the CEO. You should be able to report that to the board. Then you have the live functions. And so this is actually a really neat story, but if you were to go on YouTube and you go true to the core, one of the most profound sessions that occurred, that occurs every dream force is usually it's Parker led, but somebody on the product team gets up.

Mike Milburn (30:14.578)

And the audience can range from five to 10,000 people. And they lead a conversation of, we being authentic with our roadmap? And this is a really neat conversation because there is no sales team. There's no success team. It's just the customer and Salesforce on stage. And what Parker does a great job of it is navigating. Every customer is going to have wants and needs. Everyone's got their individual requirements, et cetera.

And those fit either in, no, we're not going to do that. It's the wrong thing for us to build. We're thinking about it or here's where it's going to be built. And over time, what I think is really neat about true to the core is it shows Salesforce commitment to listening. It shows the customer's commitment towards giving that feedback. And I don't have any data or stats on it, but I would guess that, you know,

The reason why, the reason why that's so effective is the customers feel that their voice matters. And so if you combine both those things and you have sales radar and sales intelligence telling you what is necessary to drive a sale. And then you have customer intelligence coming through and saying, what do you intend to build?

And then you have something like true to the core, it could be exec round tables, or it could be dinners or whatever mechanism the company feels comfortable. Dreamforce is a very unique opportunity. What you see there is sort of like checks and balances, sort of like the foundation of the United States, right? We've got three different, bodies that help govern the United States. You have the sales team giving you feedback, the success team giving you feedback, and then you have actual customers. You take all three of those pieces of feedback and you look at the roadmap and you should be able to say.

KK Anderson (31:51.495)

with customers.

Mike Milburn (31:56.096)

Am I building the right things together?

KK Anderson (31:59.463)

And I wonder how often what the customer says is different in fact than the others

Mike Milburn (32:06.338)

You know, it happens. mean, I remember some very contentious, true to the core sessions and you kind of have to be candid and say, is this the right thing for the company to build? mean, the more customers you get, the more the need, do the needs of the many outweigh the needs of the few or the needs of the individual. Also here is the difference between like core product and customizable. So it's one thing for customer to say, I want this turnkey.

KK Anderson (32:28.977)

Mm-hmm.

Mike Milburn (32:32.918)

It's another thing to say you could do this and here's how you would do that. My opinion is that customers want transparency. And just because a customer wants something doesn't mean they should build it, but they deserve to be, they deserve to be heard.

KK Anderson (32:47.894)

I have a question. Just real quick, Mark, if I could, you talk about the three releases a year and that's... It feels like nowadays, that's just... Everyone wants something in the moment. They want real time. They want changes faster. want... I mean, I know it's not really a part of this topic per se, but I guess it kind of is. It's product roadmap and it's more...

Mark Petruzzi (32:48.724)

You know what's in...

KK Anderson (33:15.215)

in a real time, faster environment? Like how is the speed of business changing how SaaS companies are releasing and updating?

Mike Milburn (33:27.234)

Yeah. So this is a great topic. mean, I think we pioneered three releases a day, you know, almost 20 years ago. I guess the way I think about what Salesforce did with 3RR was it gave you some ability to have certainty to what is coming next, what you believe is coming, and then what you believe is coming a little bit longer out. So you sort of know directionally what's happening and it was transparent.

The, I felt that same anxiety many times of customers like, want this today and I want it today. I think that's tempered or weathered with building in the right way, building trust, building safety, building security. Some things take more than a day or a week or a month to build. The important thing is that does the company know where, does the customer know where you stand as an organization? Are you being heard?

And are you delivering on it? So, you know, we, I personally felt after, after being so many, after being so many, ABCs, executive briefing sessions or customer sessions or dream forces that the customer's desire to have it today is that was less important than Salesforce being able to listen and being able to build the right data driven machinery.

It also worked where if a customer said, I want X and nobody had ever heard it, you could tell the customer, you know what? You're the only customer that we've ever heard that's asked for this. And that worked in our favor a lot of times too. So if you speed that up today and people want, know, just in time releases or they want a release every two days, I don't think it changes the equation too much. Can you quantify what is being necessary in order to sell more products?

Can you quantify what is being used to renew more products? And if you can deliver it on a frequency of three times a year, five times a year, once a month, once a day, that's great. But I don't think it changes the overall calculus of, you listening to your sales team? Are you listening to your success team? Are you listening to your renewals team? are you, Ergo, you listening to your customers?

Mark Petruzzi (35:49.348)

Excellent. All right, let's go to our third topic here and go to market execution and when product and sales teams move as one. Tell us a little bit about what world class looks like around product, sales, execution. And when we use that term move as one, I've heard you use that term and that's why I'm asking it.

What does it mean for product and sales to move as one?

Mike Milburn (36:19.788)

Yeah. So.

Mike Milburn (36:24.5)

One of the great parts that I remember about our internal QBRs at Salesforce was having the sales team kick off or the sales team wrap up one of my product conversations. And imagine your CRO standing up and saying, I'm not the chief product officer.

Or I'm not heading up product, but I'm excited about the roadmap and here's why I'm excited. I'm going to go sell this because I believe in it. Now, all of a sudden you're showing alignment with your, with your critical sales component. And I think a lot of the internal meetings turn into sales is the sales job. Product is the product job and everyone just kind of goes off into their silos. So it starts with that message. Does the head of sales.

Can they deliver the product roadmap? Can the head of sales demo the product? And this is something that I just find really, really unique and interesting, but I mean, I think it's still the case today that almost every executive at Salesforce is responsible for demoing their product. And there's products that it doesn't make sense and there's really technical and I'm sure we can find corner cases, but it's pretty powerful when the head of sales is able to...

KK Anderson (37:18.897)

Alright.

Mike Milburn (37:43.064)

demo in some capacity, even if it's not the world's greatest demo. So I think those two things are one and two. Three is almost no airspace between the roadmap and the sales team. We've touched on it all throughout this conversation, Mark, but you should never ever hear from any sales team. man, I wish our roadmap was different. And I think you hear a lot of that kind of in the background or hallway conversations or exit interviews or.

Maybe I'm linked in. Sometimes you hear a lot of that. And conversely, from the product team, selling is hard. And so when you involve the product team in selling and you start to see the art of selling and the science of selling, you're going to see a lot of of sympathies and a lot of energies, know, timely today. Just today, I saw.

a CRO for one of the companies I led, he left one company and went to a new company. And when you see the product team respond to that and saying, you're going to do great, John, keep going, we loved working with you. I think that's the job of a CRO is to build those relationships that maybe said a different way. If a CRO is interviewing for their next job,

Why wouldn't the chief product officer be one of their key endorse ease or endorsements? That would be a true testimony.

KK Anderson (39:12.455)

Yeah, it really would. And, you know, take the CMO, the CPO and everybody. what's your, we have recently recorded a podcast with Kathy Minter and she talked a lot about the concept of the unified CRO and having sort of one leader that is overseeing marketing, overseeing product, overseeing customer success and in that way, rather than.

know, silent. What are your thoughts around that? Some of what you just said had me thinking.

Mike Milburn (39:48.364)

Yeah, I think there's some really exciting, I think there's been some, I think there's really exciting new roles that have been created both from CEOs and CROs, you know, and I think the CRO that is just revenue generating or just sales generating, think, I mean, first of all, it's an incredible job with a lot of responsibility and a lot of accountability.

But the inputs for that are things like marketing and branding, top of the funnel, the creation of pipeline. So if we're able to understand and navigate brand and marketing, then that's almost a next generation CRO leader. Same thing with system engineering. I've seen customer success fall in there. So it really depends on kind of the company and the investors and kind of the...

Also the candidate and the kind of role behind it. mean, at Salesforce, if you look at the current organization, it would be really bad form if you were a sales leader and you couldn't articulate the product or you couldn't articulate the message. Salesforce is lucky. 25 years later, everyone's on brand, everyone's on message. They have the enablement departments to go through that. So I think part of what you're asking, KK, is like you have

You have smaller companies, medium companies, bigger companies. You have all these different sizes of companies. Then you have private equity investors. And I think this is also an important point that, you know, in the in kind of the previous model, when companies were publicly traded or that was your goal is to IPO and be publicly traded company. Who was your accountable? Who is your accountable stakeholder? Wall Street, the stock price, right?

Now with private equity, they have a different set of goals, a different set of goals and a different timeframe for that. So what is the organizational structure that's going to drive value creation? And so I think you're seeing some consolidation in some of those roles, which is really exciting.

Mark Petruzzi (41:59.556)

And Mike, think you just set up our next podcast together and I don't think we've ever brought you by me back super fast, even though we've had amazing guests along the way. But I think we have to have a discussion after this about getting you back in in the next few weeks and talking and going more deeply into that private equity, private equity and sales, private equity and how that affects strategy within.

All these companies that you work with and and we do KK myself as well Yes, we're running lower on time here, but I'd like to get into topic for scaling product sales alignment frameworks for high growth organizations and I think the the core item here is when you when you scale from early stage startup to enterprise

How does this product sales relationship need to evolve? And how do you make that work? Because we all know these early stage companies of today are going to be the sales force of 2030. So, or at least a couple of them are. Not many, but a couple. And how do you navigate in each environment to get to that full scalability?

Mike Milburn (43:24.096)

Yeah, great question, Mark. you know, with all the turnover, all the growth and all the pace and speed that the tech ecosystem is in, here's a couple pieces of guidance. if you're the CRO and there was an impromptu board meeting, could you articulate the product roadmap and give your editorial and a data-driven decision on why it's good or conversely why it's bad?

Not subjective, not your opinion, but can you give a data-driven, supportable articulation of the product roadmap that, you know, that can you articulate that? That's thing one. Thing two is, are you listening to the customers in your, again, your sales teams are spending all of their time with customers. Are you bringing the product organization

critical information about the customers buying decisions, their needs, their wants, and are you giving, are you helping another organization build the right roadmap? Number three is, have you done, here's a litmus test one. Have you done a product tour with your top customers and your CPO? Nothing will flush out a correct alignment.

or an incorrect alignment better than a dinner or lunch or breakfast with 10 customers, head of sales and the head of product. There's nowhere to go. The door shuts. They start asking questions. What about this? How does this work? Can you have you done that before? And so I think those are three things. If I had to invoke a fourth one, it would be imagine your board meeting and reverse it.

Imagine presenting to either your private equity investors or the public counsel and imagine talking about the product roadmap and your alignment with your CPO. That's, think, what your job is as CRO is to build that alignment and build that trust.

KK Anderson (45:30.449)

So when you were in the beginnings of Service Cloud and you were there with a front row seat, what, any stories come to mind around how that scale and what that experience was like?

Mike Milburn (45:40.268)

Yeah. I think I shared this earlier. The first meeting I had when I was the GM, was terrified. I thought I was responsible for innovation and I had to figure out all this stuff. I was very, very intimidated by that opportunity. Parker leaned over and he made it just real normal. goes, just listen to what they say. Just listen.

And I listened to the sales team talk about, you know, here's the size of the opportunities. Here's the data coming. Here's the telemetry coming out of sales. And then I listened to the telemetry coming out of success. And the picture that came out of that was maybe it was 80%. Right. It was let's build this to drive more sales. Let's build this to build, to help do success. And I didn't have enough calories to, to, to do everything. So then I asked for help and it was, peer group.

How would you slice this? Would you do 80, 20, 20, 80, 50, 50, 70, 30? And I navigated that success together. And eventually it was the head of sales who became incredibly supportive of my roadmap in service cloud, which led to growth. And so the head of sales became one of our biggest advocates. so I think that story, KK, kind of, you know, while it was...

very, very intimidating and I had a of anxiety going to that meeting. It's sort of, reflect on that and Parker was exactly right. If you listen to what the sales team is providing in data driven organization, then the roadmap becomes almost a fulfillment exercise of how are you going to deliver that in the shortest amount of time? And the innovation is going to come from your product and engineering organizations on how you're going to fulfill the most amount of those things in the shortest amount of time.

Mark Petruzzi (47:35.232)

Excellent. All right, let's jump into our rapid fire segment here because I can't wait to hear some of these here from your perspective. So, you you're not a CRO. know, that's not kind of not your core, even though you've done so many amazing things over your career. So I guess this question becomes, you know, when in your career have you been asked to sell and what what product or service

was the first one you've ever really got your hands around.

Mike Milburn (48:09.506)

Yeah. So I've carried a bag. Actually, Mark, I've been responsible. I've never carried a bag from an AE perspective, but I've been responsible for revenue four or five times in my career. And believe it or not, the first is going back to Salesforce. At a matrix organization, I had no salespeople reporting to me and I had all the accountability of revenue. So I had to stand up in front of Mark and team and the board and, and, and, and announce that. So.

That was really the first one. And then every company since then, I've had some relationship, either direct or indirect, with the ownership of revenue.

KK Anderson (48:50.983)

Okay, who is your favorite, let's say CEO or C-level business mentor to follow?

Mike Milburn (48:59.34)

Yeah. So I think, so first of all, I keep an internal board of directors. And for me, what my internal board and my internal mentor do is, is they allow me to be accountable to people that I value. And one of the sales leaders that was at Salesforce, that was running one third of the company for a large majority of that time was a gentleman named Dan Del Degan, affectionately known as Triple D.

And, Dan came out of Oracle and then was it hugely influential in the growth of Salesforce. Dan later on, joined Greg Buchholz, the founder and CEO of Spring CM and Dan became the president and they sold Spring to DocuSign. Dan is probably the, gentleman that I count as my chairman of my board to, to hold myself accountable, but

I think the way that he operates in his value systems, a sales oriented to the topic of this conversation, a sales oriented CEO, I count Dan the top of that list.

Mark Petruzzi (50:03.203)

Excellent. So yeah, what about a tool that every product leader, well, let's do two of them here. Since you've managed these in a dotted line way, you're responsible for this revenue, you get to see the good, bad, and the ugly, and you get to see it from a slightly different vantage point than if you were.

a CRO managing that team day to day, which I think is going to give you even better insights to these questions. So what tool would you recommend every sales leader use to ensure they are aligned with the organization? And then is it any different for a product leader, any different recommendations there as well?

Mike Milburn (50:48.578)

Yeah. So I had the, I had the opportunity to build these tools. actually the first company I left after Salesforce was Salsify and we built both of these tools natively mark. chose Salesforce for those things. as a, as a platform, on the, on the sales side, think building the data model to be able to support what is sales need. I think it makes sense to build natively on Salesforce. It's close to the opportunity. It's close to.

leads opportunities, close one, time in sales stage, all of that makes it very, very simple. On the reverse side, it's really about usage and adoption. So, you know, there's a number of enterprise tools. I don't think I'm wedded. don't have a favorite, but what I want to know as CPO is who's using the products and what does usage and adoption look like?

from a telemetry standpoint on a good customer and what does it look like on a bad customer? So I almost think about like, I want the customer's name redacted and I wanna see usage and adoption and I wanna see those trends and I wanna see what's working and what's not working. Then I wanna start asking questions. So every product has got their own internal telemetry tools.

I'm not wedded to any of them, but I really believe in usage and adoption to drive the customer success product roadmap.

KK Anderson (52:23.079)

Nice. Okay Mike, what advice would you give your 21 year old self?

Mike Milburn (52:30.95)

I would give the advice that if I could imagine the number one relationship to build, would be the relationship between sales and products and never ever have a conversation that sounded or looked parochial about. wish sales did something different. I wish services did something different. I think there's a wonderful skill of empathy. And if you're a product person and empathize how hard it is to carry a bag and you're

family's livelihood is dependent on you selling something in some frequency, and you reverse that from a sales position, understand how hard it is to ship and QA and deliver products. I think it's the empathy between sales and service, sales and product, I think is just something I wish I'd spent more time on earlier in my career.

Mark Petruzzi (53:19.649)

I mean, Mike, isn't it just the kind of the secrets of life, you know, having that that empathy in every situation and anybody you work with or coordinate with from a business or personal perspective. So I love the way you just described that. All right, let's close up on.

Let's just say this from a product manager, a product manager perspective, somebody who is the CPO taking that role for the first time. Are there any books that can give a little bit of the tricks in the trade that you've read or do you just need to get the work and write that so we all have that insight?

Mike Milburn (54:01.41)

You know, it's a great question. The one that comes to mind is actually Mark's first book. I think it was Behind the Cloud. And it just boils it down into such, from what I remember, it's been a couple of years since I read it, Mark, but it just boils it down into the raw distilling of what it takes to create a product and get people to sell it, use it, and adopt it. And, you know, in those early days, in the first five to 10 years of Salesforce,

We did so much evangelizing, so much listening, but there was so much passion behind it. And so I think that's probably a pretty good place to start.

Mark Petruzzi (54:39.615)

Excellent. Well, we have kept you a minute more than we asked so we want to keep you on schedule for your day But Mike, this is such an honor. It was so great to to dive deep into some of these subjects with you So great that I feel like we should do it again, but we'll figure that one out from here

KK Anderson (54:56.423)

Thank

Mike Milburn (54:58.36)

Sounds good, guys. We'll talk to you soon. Great to be here. Cheers. Bye-bye.

KK Anderson (55:00.313)

Thanks Mike.

Mark Petruzzi (55:00.727)

All the best.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This special episode kicks off our Mastering Sales with AI series with a candid, high-impact discussion on how revenue leaders can move beyond AI buzzwords and actually apply intelligent selling strategies—especially in volatile markets.

Stephen Messer and Paul Melchiorre join Mark Petruzzi to break down the hard truths about what makes AI work in real sales orgs: leadership alignment, data readiness, and daily execution. This is your first step toward modern, adaptive selling—driven by signal, not guesswork.

What You’ll Learn:

• Execution Beats Ambition: Why success with AI doesn’t start with big vision decks—but with specific, high-impact use cases.
• Your CRM Can’t Keep Up: Why traditional tools break in volatile markets, and how neural net AI models adjust in real time.
• Forecasting Needs a Reboot: How daily deal signals—red, yellow, green—are replacing “gut feel” and weekly sales meetings.
• Buyer-Centric Strategy: Why studying sellers won’t help you predict revenue—but studying buyers will.
• Leading with Insight: How top CROs gain board trust through data, not opinions.

Key Topics:

• Moving from AI theory to operational reality
• Fixing broken forecasting processes
• Leveraging volatility as a growth advantage
• Redefining enablement with signal-based coaching
• Why AI is a co-pilot, not a replacement
• How to scale insights across sellers, teams, and time zones
• 
  

Event Recap – Top Takeaways:

• Start small, win big: Tie AI to real revenue use cases.
• Clean data wins: No insights without data discipline.
• AI empowers, not replaces: Give time back to sellers, and sharpen execution.
• Execution > tools: Adoption follows alignment.

🎧 Listen now and follow Selling the Cloud for more episodes in our Mastering Sales with AI series. New sessions coming soon.

Mark Petruzzi (00:39)

Welcome to this special edition of the Selling the Cloud podcast. Today we're digging in one of the most pressing questions facing revenue teams right now, today. How do you sell and lead when the market gets shaky? We're thrilled to be joined again by our friend and Selling the Cloud regular, Stephen Messer, co-founder of Collective Eye. Stephen is a serial entrepreneur, investor, and one of the most innovative thinkers

when it comes to applying AI to real world business challenges. With Collective Eye, he's created a platform that brings predictive sales intelligence, once reserved for Fortune 500 companies, into the hand of every seller and sales leader in companies of all sizes. As economic uncertainty rises, many organizations instinctively pull back, but strong sellers and smart leaders lean in. Collective Eye helps them do that with confidence.

providing real-time insight into which deals are likely to close, where risk exists, and how to act before it's too late. In today's episode, we're gonna dive deep into three key topics. Why volatility separates strong sellers from the rest, and how leaders can help their team step up. Why traditional forecasting tools break in a shifting market, and how AI gives you the edge.

and then how to create urgency when customers are tempted to delay and how to guide them to take action. Okay, let's jump in. Stephen, welcome back to Selling the Cloud.

Stephen Messer (02:17)

I love being here. Thank you, Mark. Thank you, KK, for having me. You know I love talking to your audience and frankly just talking to you too.

Mark Petruzzi (02:24)

We love it too.

KK (02:24)

⁓ that is

awesome. We're so happy to have you, Stephen. So let's dive into the first topic, which is how volatility reveals the real sellers. Like, will the real sellers please stand up? And so right now, one of the things that we're seeing across, you know, so many of our clients is hesitation, right? And it's exposing when deals stall and push and delay, it's really exposing sellers

who have relied historically on tailwinds or relied on having a ⁓ well-known logo that they're selling for. And strong sellers, right, they're typically going to thrive in this kind of environment because they're truly meeting the needs and the outcomes of the customer. So what, like in this, just kind of backing up a little bit and thinking about how you sell in volatile times, like what,

What do you see or what do you think top performers are doing differently than them?

Stephen Messer (03:29)

Yeah, well,

let's talk about top performers, top organizations, because remember market share is always hard to get in any market. But when there's change, that's usually when markets shift pretty dynamically. And volatility is something that a lot of organizations are sitting today looking around and realizing that they and their architectures are very rigid. They're not very flexible to make change.

They're also not getting feedback loops fast enough. And that translates from leadership down to seller. So I say that because, you know, historically we're well, let's put it this way, market volatility, especially when it's external volatility can be very hard to understand. You're asking an individual seller to figure out what's going on or the organization is coming to a group think mentality. And the reason why that's so challenging is because they're using themselves.

to try to figure out what's going to change in the world. I think there's nothing harder, right? One, your assumption is it's you. And then the second thing is your assumption is somehow the group think will get us there fast enough. But I think what you've heard me say this before, which is the hardest part about listening to your customer in a high volatility, especially when it's negative market impacts, which is really what we're living through.

right now is sort of these shocks to the market that keep coming every other day. And that makes it very hard. What you're hearing from your customer and what their conversations are with you aren't going to help you. They're giving you sort of the Instagram view of the world. And I always joke, the happiest couples look on Instagram in the two months prior to their divorce. They're out there telling you what a great thing is. And I think when market challenges arise,

A lot of your customers are afraid to say we're hitting headwinds in our market. That's why we may not be buying and or other things that are going on because they're not sure if it's just them or if it's everyone else and nobody wants to look like they're in trouble because that creates a death spiral and all these other things around it. So what I think I'll highlight is you are talking about the sellers who are able to pick up on those subtle signals or are testing and trying messages almost immediately to test for what's really happening.

as opposed to playbook people, or as opposed to people who are just trying to follow the med pic steps. They recognize that as soon as the market changes, I have to start figuring out and sensing what's going on in the market. I think that is one of the more important things to do. But I think I wanted to bring back, because everyone thinks, no, ⁓ it has to do with an individual. So I think it's the whole work fixating on themselves, not trying to understand what the entire market's telling them.

and the best people know how to do that.

KK (06:24)

Really interesting. ⁓ So what if we think about the end-door performers? Like how do, like the ones who aren't pushing and asking the right questions, like how do we, like if I'm a sales leader, is kind of what I'm getting at. If I'm a sales leader and I've got a sales team, I'm gonna have some strong sellers and medium sellers, probably some low sellers. How do I know?

How do I know when the times get volatile like this, like who's doing what needs to be done? Like how do I know what's real, what's not, who has happy ears? What do I look for?

Stephen Messer (06:51)

Yeah.

Yeah.

Look, Warren Buffett always said it best when the tide goes out is only when you see who's naked. And I think what a lot of the sales organization is going to experience is that a lot of the people that they liked the most in sales were the people who followed their playbooks, were there people who followed the steps exactly. They may, they're probably never the top producers, but they liked it. And what's happening now is

the market has shifted and all those playbooks fail. Always, inevitably. They're doing yesterday's messages, yesterday's sale, yesterday's behavior. And by the way, all their systems are looking at, especially if they're using the older form of AI called machine learning, they're probably looking at the last two years to predict what's going on today. Nothing to do with what today is. So all their systems are falling apart.

There's probably a few outliers that are their best sellers and historically been their best sellers, but never listened to anyone, never cared, never paid attention. Those are the players that are best. And I bring that up because those are the players who are just going about doing their job of selling. But the top producers are on their own. All the systems that you're looking at that people have installed.

you know, unless they're neural net, they're not adjusting daily to what's going on. So they're all their entire systems are falling apart. Can I, can I give an explanation of what I mean by that? All right. I want you to imagine that if you pick the technology, the older workflow technologies, you know, for forecasting, for deal review, for conversational intelligence, whatever you're looking at, they're all looking at just your company's data.

Mark Petruzzi (08:35)

Yes, please.

Stephen Messer (08:53)

for the last two years and using machine learning to look for the average. called, it's a regression model. They're looking at what's the average. So they're trying to figure out whatever worked over the last two years is going to be assigned for what works today. That is a real problem. And I'll give an analogy to try to make it easy. I want you to imagine a plane where all your gauges will work fine so long as the plane is working perfectly.

But if an engine catches on fire, something that hasn't happened in the last two years, all your gauges break. Now, I want to be clear. The only time you needed the gauges was when the emergency came up. But they're all designed to break the minute there's something new or unusual that occurs. So if you are using the most common tools that are out there, I'm not going to name their names.

Cadence tools, forecasting tools, et cetera. And they're not like Collective Eye where we're using entire networks in a neural net. What's happening is they're not adjusting to the change. Everything just looks like it's broken and you can't figure out what's going on. So you've lost all your tooling to understand daily change. think of this. Most people are still doing weekly forecasting. Or they're figuring out that deals don't work at the end of a quarter.

So when you're having volatility, think about what's happened in the last five days, ⁓ Tariffs on, tariffs off, tariffs doubled ⁓ to China. Then it was the Federal Reserve Chief is gonna get fired, then he's getting saved. I mean, I can go through the dailyness. And by the way, this is like the first 120 days. Like, this is like not minor stuff. And everyone's trying to look at their tooling to get a sense of what's happening with their deals.

And that tooling is using the last two years that had none of this to decide what's going on. I think that's terrifying. If I'm them, you're flying without gauges in fog. You are literally trying to hope for, does anyone see anything? Does anyone hear anything? I don't know how you do it. And this is a good warning. We're shot over the bow that if you don't have, in our world we call it collective, which is obviously our name.

Which is if an AI like a neural net, these newer types of AI aren't learning from everything going on, you are literally trying to ask the people in your org to figure out from a limited amount of data what's actually happening on a macro level. I think that's crazy.

Mark Petruzzi (11:31)

Yeah. And it's especially crazy, Steven, when we're also in the midst of software and SaaS, software as a service, being entirely different in the world than ⁓ AI. So maybe we can touch a little bit there and maybe tie it back to how the sales leaders leverage the new tools to leverage and figure out who their highest performing reps.

Stephen Messer (11:43)

displaced. Yeah.

Mark Petruzzi (12:01)

and highest potential reps are going to be in this new environment and in this new technology space as well.

Stephen Messer (12:09)

Yeah. Look, ⁓ I think in these times, there's two types of leaders. There's the back to basics leaders. All right. These are the guys where they're like, my God, we're going through this, but I've experienced other problems in the past. So I'm going to follow my old, wait, look, I just really need people to hunker down and do this thing. Now that's kind of like when Walmart started getting hit by Amazon and

I could see Walmart executives being like, it has nothing to do with online shopping. What it has to do is we have to get back to better greeters. If we could just do the basics really well, then people come in, people love greeters. You can't do that online. Like you could see this kind of logic. Back to basics, people don't realize that the world is the paradigm has completely shifted. And now again, I wouldn't say this if it wasn't for we're in the midst of this AI revolution where everyone's doing these things. Cause if you had traditional tools and a market collapse, fine.

That may be what you do is back to basics. But in the midst of a market change, what happens is people retool everything when they realize there's a better way to handle a downturn like this. This is what happened. If you think about the dot com collapse, everyone shifted over to digital marketing. We came out of the dot com collapse and more companies had web presences, more companies had.

Uh, online shopping more companies had shifted their advertising from traditional things like television, radio, and newspapers to online. Like the entire world shifted. switched to Google, like everything moved because there was a better approach. Well, let me tell you, there is another kind of manager that looks and says, okay, everything is changing. How do I now adjust to it and what else, what is going to happen? And if you think about the AI first sales organization, we are not talking about people who are thinking weekly cadences.

Right, you've seen this Mark. Daily optimization means you're adjusting to what's happening to your customer, but you're starting with studying your customer. That's what these models do. Like in our model, our customers, we track 5 % of the globe's economy is feeding this model. That's all feeding back everyone a daily view. You know what that's going to happen to your customer before they've told you just cause you're getting feedback loops.

Mark Petruzzi (14:17)

Yeah.

And the old traditional approaches of this, that your competitors, they're just looking at what happened two years ago and what's happening in that company. There is nothing about the buyer and the buyer's journey and what's happening on that side and what the thought process is. And that's where these AI tools that are especially yours being built in a collective fashion

You're getting perspectives and guidance and coaching from your buyers as well. It's not just coming from you or your team because by their actions, your buyers are coaching you on what you should be doing next.

Stephen Messer (14:51)

Yeah.

Look, think about it this way. You are literally, it's April 23rd. For most of the SaaS world, this will be the end of their fiscal year in a few days. And I'm going to bet you that there are a whole bunch of leaders out there who are freaking out because they're going to rely on the last day or the last few days to try to figure out what's actually coming in. And they're relying on quantifying the opinion.

of all their reps of what's going to happen as the world is changing. I, as someone who's out there, can't tell you. I can watch all the news in the world. I still don't know what it's going to mean. But my neural net knows exactly what it's going to mean. I can start to see which deals that I thought were good are starting to go red. Because I promise you, if they're a manufacturing org, or they sell to manufacturing orgs, or they're dealing with people who have to import products, their world is changing. But I bet you there's a lot of people you didn't think were going to have downsides that are now.

having downsides or reconsidering purchases because they just want to wait and see. And I bet you nobody's paying attention to that because they think I'm going to get this deal over the finish line. I'm going to have to do a little bit more discounting, but I'm going to get it there. And I think they're going to find out discounting is not the problem.

KK (16:11)

It's not a race to the bottom this time. And so a couple of things that I'm thinking about as I listen. So one, it feels like the last decade, the theme de jour before the AI revolution really was process. Write your sales process, document your process, have everyone doing the same thing. And then we've got all of these systems that allow like

very generic, know, spray and pray is what we call it, know, cadences and, and outreaches and everyone, you know, it was all around activity and process and not really necessarily the right activity or even the right process. Right. And so now with volatility, right, that, that you don't want your sellers like the blind leading the blind, right? You don't want to be like an ostrich with your head in the sand while the

you know, with happy ears, right? That's something that I keep thinking about a lot. so a sales leader needs to be agile and they need to be able to like move on a dime and bag some of the stuff that they've been doing that is actually causing them to go slower. Like what's your thought on that?

Stephen Messer (17:31)

Look, this is the terrifying thing of what's happening when you have these grounds swells where everything changes, these paradigm shifts that hit. People are really afraid. used to call it in my last company, we used to call it the Tarzan syndrome, where they're afraid to let go of the rope that they're holding onto until they firmly feel they understand the new one. But you never really hold onto the new rope if you're holding onto the old one so tightly, you're just never gonna let go. And what you saw during the dot com change,

really when that switched over is you saw changing of the guards. There were some people who just wouldn't let go of the rope. And there are other people who like, this is a time we have to change everything. And I fear that, you you brought it up first. I have heard crazy things like forecasting is a process. Well, if forecasting was a process, Goldman Sachs would have the ultimate process. They don't. They recognize that volatility is the norm. Like this is what neural nets are great for. If you have a large enough data set, we've spent 10 years.

tracking the globe's economy, building this model to do this stuff. This stuff can change the way you think about things. I've also heard people tell me how buyer centric they are while only studying their seller. like, there's like, there's a point where you have a realization. Life makes things hard to make it easy for you to change. Not everyone gets that message. Sometimes they think hard is what you have to work through.

Mark Petruzzi (18:41)

you

Stephen Messer (18:56)

No, I would say if you're sitting there today, if you are watching this and you were wondering, am I going to make my end of fiscal year? Because you are sitting there worried. You have put in place all the wrong systems. You think it works because it worked for 10 years and you are mistaking that what works in the past will work in the future. That is like saying, I'm going to give them all my salespeople quarters to call me from the road because cell phones don't exist.

So I'm not going to think about my Salesforce as having a computer in their pocket because now it's a smartphone. Like you change with the times. And if you're using something you bought five years ago, you are using an infrastructure that makes no sense for the modern world. You just haven't gotten there yet. So KK, you are right. I will tell you what the new sales org looks like. And you know it because it's your best sellers are already doing this. One, it is one to one selling. If you are doing mass marketing,

Cadence tools, auto dialers, SDRs, I will tell you that is going the way of the Dodo. You can call it a cadence, I promise you your customer's calling it spam. And I know that, and you know that, because when you get it from other people, you think to yourself, my God, I can't believe they sent me this message. I will tell you a few more things that they already know. They're not answering their phones anymore.

They're not like these are heads of sales who won't do the stuff that they're telling people to do bombard people. No buyers want you to know them. So why do I bring that up? If you had a daily feedback loop and you guys know this more than anyone else when you see a deal go in the odds change and go down you change your pitch to adjust to what's happening in the market. I'll tell you we sell volatility now. If you are worried about volatility that is why you need daily forecasting with traditional process forecasting as an example.

You're going to get a weekly forecast based on people's opinions. I need to know what the world is telling me daily. That, that is the message we didn't sell prior to 90 or 120 days ago. It's a feature of our product. You all have features of your products and services. You're figuring out which features of your products matter more. But if you can't recognize that the old pitch isn't working or not working for this buyer at this company in this region on this day, if you're not getting a daily feedback,

You're not going to, you're going to try one, two messages. Yeah, maybe good luck. hope that's enough. Ours we're trying six, seven, eight, nine, 10 different messages with different people. And we all collaborate so we can share which messages worked in which scenarios. And we're sharing that across our whole company. It means we're getting at bats much more frequently. And our message in 90 days, I can tell you has dramatically changed and will continue to change. That is the playbook. Now everybody is unique. Treat them that

KK (21:46)

Hmm.

Mark Petruzzi (21:47)

Yeah, yeah, beautiful. Let's move to ⁓ topic two. And maybe we'll even switch it up a little bit. Topic two is when forecasting breaks, what to trust instead. But I'd even like to take it a step further and just put it out there to your point when everything has changed and will continue to change in ways that we're not used to. We're not used to the

know, speed of change keeps getting faster and faster. And it's, it's kind of been unleashed. It's, know, we, got a real feel for it during the pandemic. You know, I think amazingly, most companies were able to really be nimble and efficient in that. But they're, they're gonna, they're gonna have to get used to that being the, the standard, not the exception. So when you look at that and you look at just general forecasting tools,

Stephen Messer (22:16)

Yeah.

Yeah.

Mark Petruzzi (22:45)

you know, most forecasting tools or anything that's called the forecasting process is pretty much looking only at historical data. And when the market's changing as quickly as it is today, that data becomes irrelevant very, very quickly. So what are the biggest risks in relying on those outdated forecasting methods? you know, and where does it even go from here? Because...

your product is going to keep evolving and changing and daily forecasting is going to turn into hourly forecasting.

Stephen Messer (23:19)

Yeah. You know, you're a hundred percent right. mean, I will tell you, we could turn on hourly today if you wanted, by the way. We're already set up for that. think, if your forecasting process relies on interviewing your sellers, if your forecasting process relies on using machine learning only on your data, yourself, I think...

KK (23:39)

your own core force instance, your own, yeah.

Stephen Messer (23:43)

You are driving a car through your rear view mirror. You are going to crash into something. It is inevitable. It will be deadly. It will be bad. You just don't realize it because you think it's better than it was last year. And there was a period of time when you only had your own data to make predictions on. I look the reason why we look at our whole network, the reason why our customers pull it, the reason why the Wall Street Journal called us the ways for sales.

KK (23:46)

Eee.

Stephen Messer (24:13)

was because our assumption was it was easier to study the buyer to predict what the buyer was going to do than studying the seller to predict what the buyer is going to do. That should be obvious. It is crazy. There is an insanity that thinks that by studying my seller, I will predict what the buyer is doing. You are looking at the wrong person. These moments are the moments you realize the logic failure that you have.

If you're going daily, you are reacting at the speed your customer is feeling a pain. You will be buyer centric by its nature because you are studying the buyer. If you are doing a forecasting process, you are basically all trying to agree that none of you really know what's going on. It may make you feel good, but it doesn't matter. When we are driving on a distance in a trip that matters, we don't ask our four friends

what the trip should be, what direction we should take, and how long we will arrive. We go to Google Maps in ways for a reason. It knows about the road ahead. It's learning for more people. These are the moments you realize your systems are broken. They feel familiar. They feel good. But I think we're going to look back in a year, and nobody is going to believe that they used those antiquated systems and antiquated approaches. If you've done it for 30 years, it's antiquated.

I think this is a moment where you see a giant transformation. Now, is it that hard to learn? No. It feels like it. When we did COVID, do you remember when everyone was like, how is the country going to survive? And in two weeks, everybody learned to do business on Zoom.

KK (25:57)

Mm-hmm. It's pretty great actually when you think about that.

Stephen Messer (25:59)

This is one of those, this is one of those

moments where like you literally could turn it on. We get our customers live in no time. Literally, you could be live and have it. Yeah, you could literally be there tomorrow seeing how it works. And you could use people like you guys and say, how the hell do I use this thing? It is so easy. It's fear. But you know what? These moments drive people to have to overcome their fear. And that's when they make these big moments of change.

KK (26:08)

Right. Like, overnight. ⁓

Yeah.

Well, some of the, you know, historically, when you think back to any recessionary period, some of the some of our greatest companies were founded and took off in a recessionary time. And I'm not saying that that I think we're headed towards a recession, just knowing that things are volatile and people have the same reaction where they tend to sit on their hands. And coupled that with knowing that really and truly there's a massive opportunity.

when you have volatility like this, like this is when you can really shine and figure out how your product or service that you're selling can really help your customer solve the problems that they need to solve, like whatever it is, right?

Mark Petruzzi (27:11)

Yeah.

Stephen Messer (27:13)

You are 100 % right.

Mark Petruzzi (27:13)

And KK, just, KK, you just brought us in a great direction here. And I'd like to take the whole conversation up to that point. And I'll start it with a quick story. I've been fortunate enough to have met John Chambers, the former CEO of Cisco a few different times. And the last time I was with him, he told the story to a bunch of us about Cisco and then more generally about

his view on capturing growth and capturing market share. And his point of view is that there's never any growth that's captured or market share that's captured in high growth situations. Because in his theory, companies just, get on, they catch the wave, they get a little sloppy, which we've seen that over and over again, and they all kind of become more like each other and become more commodities.

Stephen Messer (28:04)

.

Mark Petruzzi (28:08)

difficult times and he used the example of I believe it was the Kyoto earthquake in Japan when he just instead of like taking his Asia pack unit and just going into protection mode He looked at that and he said this is when we're gonna grab market share and he took a extremely difficult market environment and turned it into a

huge market share grab for Cisco and I mean that really hit home because

We're in that situation now globally. What an opportunity to go and really look at this, especially because we have this little word that means so much now and means different things to every different person. But this little word, this little acronym AI, like you can use that and leverage it into that market share grab today.

KK (28:40)

We are.

Steven, one of the things that you always say, and I quote you all the time, is that a seller with super intelligence on their side will outperform a seller without it any day of the week. And it's like, so we've got this volatile time, which is an incredible opportunity, as we've discussed, we've got AI in our corner that we can leverage to be incredibly differentiated. Like, I'm excited. Like, I'm excited about this.

Stephen Messer (29:02)

Lucky.

Yep.

Look, if you are a seller or a leader and you're freaking out right now, you are not seeing market opportunity. You have the wrong tooling. If you are there trying to figure out, I going to make my end of quarter? And you've got all these systems that's not working. It is not working for a reason, right? These are the moments where you realize the water has gone out. I am naked. Please help me. And you can make that change and transition very quickly. I think there are companies like us.

We are grabbing market share like crazy now because they have installed all these systems. And I'm able to point out, you used forecasting example. We do a lot more than forecasting, but let's just use forecasting because you brought it up. It's taking 20 % of their activity on Friday. You only have so many days left in this quarter and you're going to give up one of them to debate with each other. Your opinions based on what news you read and what you're hearing from customers of what your outcome is going to be. Do you know how many CROs are going to get fired?

for missing their number because they had no ability to tell in advance what was going on. And the board who's asking right now, what is this going to mean for our quarter? They are saying things like, I am hearing from my teams, as opposed to, we use a product like Collective Eye, which there's only us, but let's just say, I use Collective Eye and I'm seeing that the AI is telling me.

Mark Petruzzi (30:45)

Yeah. ⁓

Stephen Messer (30:50)

this is what's happening with my deals and I know exactly which ones to go into right away and I know exactly which person to talk to and I know exactly how to handle the situation and I'm going to do my best to deal with it but here are strategies that I'm going out there with because I'm trying to do what I can to salvage this crazy market and that is the difference between someone who can show the board that they like.

I would argue a lot of these people who are out there, and I'm sorry if they're listening and you're upset, if you're thinking I have put in tooling and I'm trying to manage it, you should be fired. The board should not be relying on you or your company or your team's opinion. That is insane. Can you imagine a banker or a broker saying to you, my personal opinion was this stock was going to do well? No, you better have a quantitative analysis that tells me exactly what's happening so at least I understand what's going on.

You are not doing your fiduciary obligation by appalling people's opinion. This is insane. It's insane.

Mark Petruzzi (31:45)

Yeah. And you know what, Stephen?

Stephen, you're taking me into a whole nother point as well. ⁓ And I'll try to make this a little bit of an analogy. But first, I'll start with a premise and a hypothesis. And this is something I truly believe. But sales reps are incredible manipulators. And some of them more than others. But they are really good at delivering their narrative. And what they want to see happen

and managing up to their CRO, to their CEO as well. So you're doing this polling as you're describing, and you're getting all these different sales reps to kind of put in their agenda. It almost feels to me like if you were, no matter what your political background is, if you were to say, I want to find out about something that happened, the Ukrainian-Russian peace talks,

and you brought on individuals and you brought one commentator from Fox News, one from CNN and one from MSNBC and you found some of the new brands out there. I mean, could you imagine what kind of information you would have at the end of that day and how they would, you would go into one thing and you'd be told one thing and then you go into the other thing and you'd be told an entirely different thing. But that is what happens and we know it.

Stephen Messer (32:47)

Yeah.

Mark Petruzzi (33:10)

because we've all been CROs, we've all been sales leaders on this call. And that's what I've never thought of it this way. Maybe it's the political environment we're in today. But that's what some of those days have felt like to me now that I think back at them, because I would be amazed. I would have one sales leader telling me one thing about the economy and another one telling me an entirely different thing. One group that's saying they're gonna hit every one of their commit deals.

and one of them coming in and saying, I'm not gonna hit any. And then only to find out that the one that said they weren't gonna hit any hit half. And the one that said they were gonna hit all hit 30%. So it's amazing and your tool does take a lot of that out of the equation. And what it also does is it takes the wasted time because same thing, if you're just gonna listen to political commentary all day long for 12 hours a day, you're kind of wasting your time because

Stephen Messer (33:44)

Yep.

Mark Petruzzi (34:07)

no matter what and no matter how smart you are, you're not gonna get like, you're not gonna get an answer, because there's not one answer.

Stephen Messer (34:13)

Yeah.

KK (34:14)

It's impossible to

know without that. And I'll say one thing, and then I want to ask you a question about kind of trusting the data, because I know that there's listeners out there thinking, yeah, this sounds really cool, but how do I know I can trust this data? So I want to go there in a minute. So for us at AGS, where Mark and I are a firm, we

Stephen Messer (34:28)

Yeah.

KK (34:37)

you know, we use collective eye. And so we, log in every morning and I, and I look at the odds of the different opportunities that, we're, that we're working on. And I always think to myself, you know, red light, yellow light, green light, right? And if a deal has an odds that is like 80 % or higher, I'm like green light, everything's tracking well there. And if we have a team members that have deals that are in the yellow light, which is like, you know, I would say 60 to 75 % or 80%.

Stephen Messer (34:50)

you

KK (35:05)

That's where I'm now gonna spend my day. And when I make that phone call to our seller and say, hey, how can I support, how can we create differentiation in XYZ opportunity because it's a yellow light, right? And I know that we really want this and this would be a really great win for us. It's a yellow light. Like, what can we do to really make sure we understand everything at play? And then that's a true coaching conversation, not a...

Stephen Messer (35:33)

Yeah.

KK (35:34)

you know, saying the same, you know, stuff to every single salesperson that you talk to on every single call, you feel like you're saying the same thing like a broken record, right? So that red light, yellow light, green light is really cool as far as productivity and being able to coach in the moment, those types of things. But take me back to how do I know I can trust this? Like I know we're going to have some skeptics out there.

Stephen Messer (35:43)

Yeah.

Look, there are, look, my ideal a lot, as you know, with a lot of people say they're snowflake, our business works differently. Our, I would say there's two things to realize. One is everyone thinks that the challenge that they went through to figure out how to sell their product is what an AI has to. And the other thing is they think they're selling a product. Here's what makes all this stuff work so well. One is just understand we're studying the buyer across everyone in our network. It's pooled data.

It is like Google Maps. learns from every driver. what part of the challenge that the selling team always is dealing with is trying to figure out how to sell their product, but they don't realize it's a random walk. Their buyer is going through a buying process. They think they're selling it. No, they're going about their process of buying it. Their process is pretty consistent. They're pro. In fact, if you've ever had a customer, you're selling every month.

more more stuff to you know their process really well. You know exactly how long it takes. know who needs to sign it off. You know how to pick that one pretty well. It's all the fact that you're selling to new customers all the time that it looks like a random walk. It is things that are feeling similar. It is things that have kind of commonalities, but generally it's a buying process. So when we study that buyer at buying organizations all day long across our network, we're able to make really good predictions.

We're taking in your data to learn about you. Yeah, there's some uniqueness. We're going to learn about that. But generally, we're learning that. So the first thing is conceptually recognize that what we're studying is the actual person who can make the decision and their team and their company and everything that's going on all day long. If you understand that, when you start to see the use of the product, because the only way you'll ever believe it is using it. If you use Google Maps or Waze,

Mark Petruzzi (37:35)

Yeah.

Stephen Messer (37:45)

And someone told you it could tell you where the police were, you would say, that's BS. Until you see your first example, or where it routes you in a shortcut, or it knows about an accident beforehand, you see an example. If I had told you three years ago about this amazing thing called ChatGBT that could draft and do all these great things, that you would say, Steve, you're crazy. But then you played with it, and you were like, my goodness. And then you played more, and you realized there's better and better ways to write prompts.

to get even better results, you start to go down the rabbit hole. There is no way that I, KK, you or Mark will convince people to believe something until they see it for themselves. But here's what I love. What I love are all the people who say, I don't believe it, so I'm not gonna give it a try. I think you need to prove me wrong. That is like me commenting, I don't like Paris, but I've never visited France.

Okay, that is not a fair representation. That is an opinion based on nothing. So if you can't take that gamble to try it out, and we give lots of free ways for people to try it out. Intelligence.com is one free way. We give people 14 days to try it and opt out if they don't like it without any cost. We do lots of really cool things to give people the chance to try it. But if you don't try it, you've got a bigger problem. That means you're just trying to reinforce your own bias.

that it can't work because you're afraid of something, whether you're afraid it's going to take over your job or whether you're it's not going to work or whether you're afraid you're going to look stupid or you're afraid. Trust me, until you're in it, you just, you don't have the ability to make that decision. Now, can I point out one last thing before I jump off that subject? Cause I think this fear is an important thing. The one group we haven't talked about that will affect every seller that will affect every sales leader and every org right now is

The only natural predator for a CRO is the board. And there are a lot of people out there thinking, I can manage the board. But the statistics of a 15 month tenure on average for CROs say boards don't believe your BS. They have gotten the place where you have spent all this money on tooling that is based on studying the seller, not the buyer.

So they do not believe anything you are saying. And if you show up at the end of this quarter or during the quarter when they're asking questions about how is this stuff that's going on affecting our business, and it starts with I think, or my team believes, you have a shark circling around you waiting to feed on you because they are thinking I have a fiduciary obligation to shareholders.

whether I'm a PE firm, whether I'm a VC firm, or whether there's gesture investors and they are saying, think, you think the entire business, we have to make decisions on how to do capital allocation, whether we should be staffing up, staffing down, building or retracting. have debt holders and your argument is I've spoken to my team. You don't have a quantitative way to say we use collective eye, it studies the entire.

sales world and what it's telling me right now is that we're going to get hit and here's where we're going to get hit or we should be doubling down in this sector because this sector is growing and we can put our money there and we can make up for our numbers because if the answer is I met with my team on Friday and we believe that we're still going to be on track.

Mark Petruzzi (41:28)

It's trouble.

Stephen Messer (41:28)

You can hear

and you can see the shark circling, thinking, how do we let this guy be in charge of our business?

Mark Petruzzi (41:36)

Well, especially Steven, you've kind of used the shark analogy, but it is the DNA of those women and men who are typically on boards are entirely different than the typical DNA for a CRO. And they are only, it's black and white. It's what are the reports show? What does the data show? I mean, that's why data as, know, leveraging data science in every function within a company

why do you think that is such an easy investment for a board to make? They're like, yes, I want more data. And I've been asking you to get more data from your customers for years. And you've got this CRM system. And every time you go and do a presentation, you start the presentation by saying, we don't really have great information on our customers. And we're trying to get better. And we're working on it. So you're 100 %

Stephen Messer (42:28)

Yeah.

We have pipeline cleanup.

here's how our pipeline's grown, but we have some cleanup we need to do. Yeah, I sit on boards. I sit on public boards. I sit on private boards. Trust me, here's what they don't see, What they don't see is the CFO comes in, perfect numbers, no opinions. The CMO comes in and shows what's happening in the market.

Mark Petruzzi (42:36)

It's the same thing.

Stephen Messer (42:55)

with quantifiable, here's how we got our cact down. Here's where we're spending. We're seeing less conversion right here. The seller comes in, leans back. So let me tell you what's going on. Here's what we're hearing. Here's what we're feeling. Here's what we're saying. Here's how we're changing. We're going to implement methodologies. We're going to change some of our hiring practices. And they're just like, give me something I can rely on. And the numbers they put in the board book come out of systems that they know are fake.

like CRM, they come out of things where they're looking at the numbers and nothing adds up because they're like, last quarter, you came and said you had 10 million in ⁓ new pipe, but I'm seeing now 15. Should I read that? And they're like, well, we have cleanup and ⁓ we still have work to do. We're still implementing some things. Our CRM needs to get redone. They're just like, what the hell is going on here? And they're done with it.

Mark Petruzzi (43:24)

Yep. Yep.

Yeah.

Stephen Messer (43:53)

That's what

you see happening when you see the high turnover. They're basically saying we have to find someone who can actually manage this business with data. And that is not a process. Let me come back to that. That is a machine spitting out trustworthy, consistently quantified, up-to-date information. I would rather be a CRO walking in saying, look, I'll show you the trend of where the AI was predicting. You can see here.

And you know, you could do this in tele. It'll say, you could see here when the tariffs went on, immediately our odds went down and you can see which deals got pushed back out. You could see the impact of that. Now the tariffs came off and you could see exactly how it rippled through. And by the way, when they asked me questions, how great would it be to be able to go on a tele and just say, okay, which parts of our business or which regions or which industries had the biggest impact? And it comes back immediately with an answer. So now you're giving them hard answers with factual information.

And then you could bring them to examples and show them. Here's where you can see the customer started saying these things and look how the odds started changing. And now they're like, okay, you have control of your revenue. You have control of your business. That's what people care about.

Mark Petruzzi (45:01)

Yes.

KK (45:01)

My heart.

Mark Petruzzi (45:04)

And Stephen, what they also get, you also get to do as a CRO there is say, okay, this even when you have bad news to report and you could say, well, this is what the numbers with Collective Eye started showing me 30 days ago. And this is what we did. And this is my response. And this is what the team came up with. And guess what? We've seen this response now. We've seen the numbers going up. We're back in a better point.

KK (45:24)

Yes.

Mark Petruzzi (45:34)

And like I do that all day long. mean, and when I started using Collective Eye, you know, I, I wanted this to be as amazing of a product. And, and, you know, for me, this started all the way back in, in work that I was doing with BCG where, you know, there was a lot of really smart people that right at the beginning were like, this isn't going to work. Collective Eye isn't going to do what it said. And, and there's all these things and these are people I respect. And so I kind of went in with first like,

I didn't believe anything. I was testing all kinds of things. The things you and I have talked about, Stephen, like where, okay, I have three meetings on an account. Well, is that gonna make my account jump up 20 points in the forecast ⁓ odds? And I've done that and I've seen it. And again, yes, do meetings and interaction help your forecast? Usually, but is it the main driver?

And right now, like for example, in accounts that me and KK have, that we've had a bunch of great interaction and emails, but the numbers are still going down because there's macroeconomic and geopolitical things happening here that are bigger than our little meetings that I'm having. That's the difference. But I love the concept and I want to just share it one more time for our audience of, you get to do this stuff almost real time.

Stephen Messer (46:35)

Yeah.

Mark Petruzzi (47:00)

and see what your actions and your thoughts and those great strategic ideas that you come up with and you get to see how it's really gonna impact your revenue at the end of the day. That's amazing to me.

Stephen Messer (47:09)

Thank

KK (47:14)

And if you're going to be like in this case, there's a deal that Mark and I

Stephen Messer (47:17)

you.

KK (47:17)

are working on right now actually, we, gosh, we feel so good about it, but man, the odds are not good and we're not happy about that. And it's telling us, you know what, don't spend five hours working on that. Go, go bark up another tree, go find something else, go prospect. You know, you, you know, it's, it's, you, you see the immediate impact of the markets on your pipeline, but then that education.

Stephen Messer (47:33)

Yeah.

KK (47:44)

just makes you so much smarter. Right? And yeah.

Stephen Messer (47:47)

So cool.

It's so cool. What's so cool about it is what you're both saying is it's hard if you haven't seen this as a someone who's watching this via it's hard to get that like you will see deals where you have tons of activities and the odds keep going down and you'll have deals where you have no activities. The answer shooting up. You're like what's going on? And what it is is that's the market that we're capturing telling you something. And so you all of sudden you're like I mean the first time you'll see it. They're like something's wrong. I didn't do anything on that. I'm like no.

KK (48:08)

Yeah.

Stephen Messer (48:15)

Pick up the phone. You pick up the phone, they're like, what great timing. You're like, how did it know? But that's the power of these network models is you start to get this wow factor and you start to realize tons of activity does not indicate that it's working well. Sometimes they're just being really polite. Sometimes even if they wanted to buy, they just don't have the dollars, but they want to learn. There's so many things you learn. And in these moments, I'll give a great example. KK called me up today and she's like, my God, the macro. She's like, I can see in certain deals.

Mark Petruzzi (48:30)

Yeah

KK (48:36)

Mm-hmm.

Stephen Messer (48:44)

that are in certain areas exactly what's going on. It's like you can see it on a daily basis. We call it cycle time, which is if I can get down to a daily feedback loop of how did yesterday affect my tomorrow. That doesn't just mean me. That means like everything. How does it, what's happening? I can now quickly react to it because even if it's just putting in a phone call to say, my God, I saw what happened yesterday with Powell. How are you guys holding up? And if they're like, this stuff is whiplash is killing me.

Tell me what's going on. Can I give you an introduction to someone? Can I help with this problem in some other way? Like, hey, do you need me to slow down because you're worried about it? You're gonna find out faster and you're gonna not invest the wrong time or good time in bad places. And you also might be able to build a relationship that grows. I will tell you, we are growing faster in the last month and a half than we've ever grown and we've been growing fast. It is because all of a sudden everyone's like, I can't.

KK (49:28)

I'm not.

Stephen Messer (49:41)

wait a week to know what's going on. And I definitely don't want to ask people who themselves don't know what's going on. And all of sudden now we're dropping in fast, showing people and they're grateful because they're like, imagine if I had this and it's not too late, right? I have a feeling we're in for a lot more volatility because the world is becoming like.

There's a risk of Taiwan going to war. There is a risk that India goes to war with China. There's a risk that the Ukraine problem doesn't get better, that it gets worse. We have Yemen shooting missiles again. We have the threat of Iran war. Like just macro things like that, yet alone what's happening day to day and the disruption that AI is causing in all parts of the business. I don't think we're going through a very volatile period, which is for me, thankfully using collective eye, my own product, because I eat my own dog food. I am excited.

KK (50:20)

your life.

Stephen Messer (50:30)

because this is the moment that people realize everything they're doing needs to change. That doesn't happen often. I want to grab it. I want every one of your people listening here to feel excited, not fearful what's going to happen each day.

Mark Petruzzi (50:35)

Yeah.

Yeah, incredible.

KK (50:44)

Right.

One thing I'll also say before we wrap up, this has been such a fun episode. It took me, gosh, what am I now? Almost 49. It took me a lot of years to get to a point where I actually look forward to challenges. Because when I see them, when I find myself in a challenge, my first thought is,

cannot wait to grow. I cannot wait to see how I get better and stronger as a result of this. I almost welcome it. I go as far as to say I'm almost looking for them. And so that's sort of the lens and the perspective that we have to have as sales leaders, as sellers going into these times. Don't be afraid to change. Don't be afraid to jump in.

That's just my perspective there. And I will say, we're going to put in the show notes here a link to be able to learn more about these great systems as well. So ⁓ head there and make sure you go to learn more.

Mark Petruzzi (51:55)

Yeah.

Stephen Messer (51:56)

Look,

pair yourself up with the super intelligence. That's my main point. I think you said it best, KK, which is, you ⁓ you can overcome any challenge if you're aware of it. If you're unaware of it, it's just you're living in fear that something is going to drop that's going to blow your quarter. Something's going to drop that's going to blow your pipe. Something's going to drop. That's not going to give you the ability to overcome it because you're going to find out far too late to fix it. Overcoming things is what makes a great seller.

KK (51:59)

Yep.

Stephen Messer (52:24)

wake up in the morning and think today is the day I earned my keep. I did something great. And if you get a daily feedback like Collective Eye gives, you will literally wake up saying, this is where I need to be, or it's not worth it. You're not going to get surprises anymore. And I love the point of we can overcome anything. KK, I've seen you do it. I've seen Mark do it. Every one of us who's listening to this has seen great people do it. If given the chance, you can overcome something.

not given the chance because you didn't want to listen, which is really what Collective Eye is doing. It's just listening on your behalf and telling you what this means for it's a translator of what the buyer is trying to tell you. If you're not listening, you're not in the game. You think you are, but you're not.

Mark Petruzzi (52:54)

Yeah, you don't have a chance.

KK (53:08)

Mm-hmm.

Mark Petruzzi (53:09)

Yeah.

Stephen, I'll close real quickly with a little bit of another story here. it's when I was ⁓ kind of college time, you know, year or two after college. Well, my whole life, I had a friend who actually went into the Green Beret and the special forces and we would always meet up and there would be seven or eight special forces, individuals with two or three of us that were

you know, the ones who don't have that kind of training and background. And I don't want to make it seem like I'm someone who would ever be looking to get into a fight in a bar or something. But there were bars that we would go to when we knew we had those Green Berets with us, then where we would, you know, we'd never even think about going to without them. And that's kind of the way I feel with Collective Eye. And you just got to use it for good, not...

not evil and that's goal.

Stephen Messer (54:08)

Amen.

KK (54:09)

Yeah

Stephen Messer (54:09)

Amen. Amen. And we will.

Mark Petruzzi (54:11)

Beautiful.

Yep. it's, well, Stephen, first off, it's amazing. We are so grateful for the relationship we have with you and your team. And we're so grateful to have been an early, early adopter and get to leverage it every day. And thank you for taking the time with us today. This was awesome.

Stephen Messer (54:33)

That's mutual and I hope your community communicates to you because they could get a lot of their questions answered really easily from you guys. You guys are power users. You're amazing. We've loved working with you. We've learned from you and ⁓ so grateful to be on today and hopefully give people some excitement, not fear around this volatile market.

Mark Petruzzi (54:52)

Yeah, beautiful. Thank you again. All the best.

KK (54:53)

Absolutely. Thank you, Stephen. We'll see

you next time, okay?

Stephen Messer (54:56)

Thank

you guys. Can't wait anytime you want.

Mark Petruzzi (55:00)

Perfect. And thanks to our amazing audience. Have a great day all. Cheers.

KK (55:00)

Absolutely.

Mark Petruzzi (55:12)

It will not let me, there we go, okay.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Stephen Messer, Co-Founder of Collective[i], continues to challenge the status quo of sales technology and leadership—this time focusing on how GTM teams can embrace AI, real-time data, and agile principles to navigate today’s complex buying environments.

Stephen and the hosts explore what’s broken in forecasting, why reactive CRM systems create risk, and how the modern seller’s mindset needs to evolve in a world where speed, adaptability, and intelligence win.

What You’ll Learn:

• The Rise of Agile Selling: Why sales leaders need to build systems that adapt in real time—not ones that just report what already happened.
• AI-Enhanced Forecasting: How predictive intelligence is helping teams eliminate bias and plan more accurately.
• Why CRM Alone Is a Liability: A deep dive into why legacy sales systems fail in fast-moving markets.
• How to Spot Buying Signals Earlier: What modern sales orgs are doing to move faster and respond with precision.
• Changing the Sales Culture: Why the future of sales leadership depends on embracing new data models and tech-forward practices.

Key Topics:

• Limitations of CRM forecasting
• Integrating AI for signal-based selling
• Buyer journey complexity and data latency
• Building an agile, responsive GTM motion
• Real-time revenue intelligence tools
• Leadership shifts for the AI-enabled seller
• 
  

Guest Spotlight: Stephen Messer

Stephen is Co-Founder and Vice Chairman of Collective[i], a revenue intelligence platform leveraging AI to enable agile sales execution. He’s a serial entrepreneur with a passion for reshaping how sales teams operate in dynamic, data-rich environments.

Resources & Mentions:

• Company: Collective[i]
• Topics: Agile revenue strategy, AI forecasting, CRM alternatives
• Suggested Reading: The JOLT Effect, The Qualified Sales Leader, The Sales Acceleration Formula

🎧 Listen now and follow Selling the Cloud for more episodes on modern GTM, enterprise sales, and AI-led transformation. Subscribe wherever you get your podcasts.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Stephen Messer, Co-Founder of Collective[i], joins Mark Petruzzi and KK Anderson to challenge outdated sales systems and thinking—starting with the traditional CRM mindset.

Stephen shares why CRM is no longer enough to keep up with how modern B2B buyers actually buy, and how AI, agile selling, and real-time intelligence are enabling sales organizations to operate with precision, speed, and adaptability. If your team is still relying on lagging indicators to drive revenue, this conversation is a must-listen.

What You’ll Learn:

• Why CRMs Fall Short: How today’s buying environments outpace static, backward-looking CRM data.
• AI’s Role in Sales Agility: How machine learning and predictive intelligence change how reps prepare, forecast, and engage.
• Modern Buyer Behavior: Why linear sales cycles are dead and what sellers need to do to stay relevant.
• Real-Time Revenue Intelligence: How agile systems give sellers an edge by tracking live signals, not just past activities.
• Breaking Old Habits: What it really takes to shift from CRM dependence to a future-forward, AI-enhanced GTM approach.

Key Topics:

• CRM limitations in today’s sales environment
• How AI enhances human selling, not replaces it
• The evolution of sales ops and forecasting
• Agile frameworks in B2B sales
• The speed and complexity of modern buying journeys
• Building a responsive, data-informed sales organization

Guest Spotlight: Stephen Messer

Stephen is Co-Founder and Vice Chairman of Collective[i], a platform that delivers AI-powered insights for enterprise sales organizations. A serial entrepreneur and digital innovator, Stephen brings deep insight into how technology and data can transform sales performance.

Resources & Mentions:

• Company: Collective[i]
• Topics: AI in sales, agile revenue systems, sales enablement tech
• Recommended Reading: The JOLT Effect, The Challenger Sale, Predictable Revenue

🎧 Listen now and follow Selling the Cloud for weekly expert conversations on the future of enterprise selling, GTM strategy, and revenue innovation. Subscribe wherever you get your podcasts.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of Selling the Cloud, conversation with Kristina Jaramillo, President of Personal ABM, dives deeper into how ABM becomes a true revenue engine when it’s embedded across the entire go-to-market team.

Kristina focuses on post-sale motion; how ABM supports retention and expansion, closes the sales-marketing gap, and helps GTM teams drive value beyond the initial deal. She also shares how executive alignment, buyer enablement, and account-specific orchestration lead to stronger pipeline outcomes.

What You’ll Learn:

• ABM for Retention and Expansion: Why post-sale ABM delivers faster ROI and stronger pipeline impact.
• Marketing-Sales Orchestration: How marketing enables—not just hands off—the selling conversation through strategic content and insights.
• Leadership Alignment for Revenue: The importance of CRO-CMO collaboration and how it drives true go-to-market accountability.
• Multi-Channel Buyer Relevance: How to use platforms like LinkedIn to drive engagement beyond generic outreach.
• Revenue-Led Metrics: What to actually measure in ABM, from NRR and deal influence to buyer group engagement.

Key Topics:

• ABM’s role in revenue beyond acquisition
• Moving from pipeline handoff to full-cycle enablement
• How to align GTM leadership across sales and marketing
• Using account insights, not just intent data
• Orchestrating account experiences across buyer groups
• Redefining the marketer’s role in late-stage deals

Guest Spotlight: Kristina Jaramillo

Kristina is President of Personal ABM and host of the ABM Done Right podcast. She works with B2B tech and SaaS companies to move beyond automation-driven tactics and build strategic, account-relevant go-to-market programs that generate real revenue growth.

Resources & Mentions:

• Podcast: ABM Done Right
• Go-to-market strategist to follow: Sangram Vajre
• Recommended Books:
• The Challenger Sale
• The Challenger Customer
• The JOLT Effect

🎧 Listen now and follow Selling the Cloud for more GTM insights from leading voices in enterprise growth. Subscribe wherever you get your podcasts.

KK Anderson (00:01.573)

Hello and welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Christina Jaramillo, president of Personal ABM. Christina is a trailblazer in strategic account marketing. Her firm specializes in helping tech and SaaS companies evolve their go-to-market strategies to land and expand six and seven figure enterprise accounts. Unlike

many ABM programs focused on automation and intent signals, Christina's approach centers on creating highly relevant one-to-one experiences that influence every stage of the buying journey and drive real revenue outcomes. And so today, Christina is going to share with us what it really takes to succeed in the enterprise space, especially for mid-market companies trying to move up market.

So today we're gonna explore four themes with Christina. First, we'll talk about redefining your ideal customer profile, your ICP, and enterprise buyer personas. And we'll talk about how do you align that? Your targeting, your messaging, and how do you get that message right with enterprise priorities? Second, we're gonna talk about fixing flawed ABM programs.

Why are so many intent-based, persona-based, ABN programs failing? And how can you rebuild them around account-specific insights and business cases? Third, we're gonna talk about what's not working anymore in B2B marketing. Okay, spray and pray email sequences, generic content, we all know it's no longer cutting it. So we're gonna talk about things that we can do instead. And then finally, fourth,

We're gonna talk about turning the marketing to sales handoff, turning the marketing to sales handoff into a handshake. We all know that there's usually some kind of an island or a gap between marketing and sales. And the real trick is closing that gap. And Christina is gonna talk to us about how we can support that handshake. This episode is packed with practical insights for revenue leaders looking to break into larger accounts.

KK Anderson (02:21.889)

improve win rates, and align sales and marketing. Let's dive in. Welcome, Christina, to Selling the Cloud.

Kristina Jaramillo (02:29.602)

Thank you so much for having me. I'm looking forward to the conversation.

KK Anderson (02:32.077)

Yes, we are so excited that you are here today. So let's jump into the first topic, which is redefining your ICP and your enterprise buyer personas. And you've said in our conversations that so many companies that are trying to move up market fail to really, truly redefine their ideal customer profile. So start with.

maybe describing what's the difference between an ICP when you're targeting a mid-market buyer or an enterprise buyer.

Kristina Jaramillo (03:08.344)

Yeah. So first off, I'm going to say that most companies don't necessarily have a ICP in the first place. They might have an ideal customer segments or a total relevant market, which is has sales and marketing teams guessing where they should be prioritizing accounts, where they should be focusing on. So your ICP is your ideal customer. So they're the ones that should be the ones that are predictive of accounts landing, expanding with you, because they align with you. They're going to align with you in a couple of ways. It's operationally.

executionally and culturally. These are the ones that are strategically ready for your solution as well and ready to implement with success. They're the ones that have a key strategic priority in place that your solution, your platform, whatever you're selling can play a role in. So no matter how much pain you solve, an enterprise is really not going to move forward with a deal if it doesn't fit into their existing strategic priorities.

These are the ones that you have a differentiated situational story to tell. So we all know enterprise deals are inherently longer and they're getting longer, you know, currently, and they're more complex. They require more time, more resources and focus. So you don't want to be wasting your time and your team's time on accounts that are most likely not going to move forward or they're going to get stuck in indecision or churn after a deal is closed. So it's really important that we redefine our ICP and keep optimizing that ICP.

because the market changes, your business changes, your customers and your focus changes. So your ICP definition is really going to make sure that you are winning or losing deals and how accounts enter or leave the pipeline. So traditionally, I still see a lot of organizations focusing their enterprise ICP on pretty generic broad.

So like industry, company size, revenue, technographics, maybe a superficial look alike. So I've seen stats saying that when you do things like that, you're cutting your win rate by at least 60%. I've seen even closer to 70. And while companies, I know it's kind of scary, but while companies are building their pipeline with these enterprise accounts, win weights are dropping. And it's a lot because companies are spending time on enterprises that...

Kristina Jaramillo (05:28.95)

are not likely to land and if they do, they might turn. And if they land, they might not ever expand. So account-based go-to market, which we specialize in, is about aligning that complete marketing function with sales, with customer success, so that we focus on the ICP as a team versus just that total relevant market, which is what a lot of companies I've seen have focused on. The ICP that you focus on are the accounts that are predictive of landing and expanding with you.

So we need to focus on what are those characteristics of those key enterprises? What are characteristics of enterprises that are strategically ready for you? So for example, most companies are not yet structured to succeed with AI. They might want to move forward. They might be very interested. They might be looking, but they're not set up if they bought an AI solution to maybe use it to its full potential. So there's a risk return, even though there could be greater success.

So what we really need to think about is where are we relevant, where our competitors are relevant, and then think about the strategic priorities where we should be looking for in a prospect. And then the situations where we have that differentiated situational story to tell. So it requires more work and it's not something that just kind of sits in a pitch deck somewhere or in a slide somewhere, it never gets revamped.

KK Anderson (06:53.093)

Wow, that's quite a lot. So...

you know, as you are shifting and, and I guess it's way more than just segmenting is what I'm hearing you say. Right. It's more around the strategic priorities. And so, so like, what are some of those blind spots that companies have?

Kristina Jaramillo (07:07.47)

Yes, that's why we need to be real.

Kristina Jaramillo (07:17.656)

think they either let marketing define it or let sales define it, or they each have their own version of it. And there's, it's not like a cohesive one that you should be able to ask someone in both sides of the team and even customer success. And they should have very similar, if not identical definitions. And I think that's why there's that disconnect in pipeline numbers and revenue numbers and closed deals and things like that. It's so that we know.

KK Anderson (07:22.906)

out.

Kristina Jaramillo (07:46.39)

It's not a matter of like aligning all these teams internally, the go-to marketing. It's really about orchestrating and moving together as one. So whatever marketing does influences sales and then sales influences customer success. And it goes all the way again, when you do up in a circle, because customer marketing would get involved if that's something that your organization has. it's, it's everyone agreeing on it. And again, that whole revisiting it, not just letting it kind of be a stagnant thing.

KK Anderson (08:12.411)

So how do you determine what those strategic priorities are that your target market might have in common, know, over and above just typical thermographics?

Kristina Jaramillo (08:25.154)

Yeah, so what we typically do is we'll go to the customers that are the best customers. So the ones that are getting the most value, the ones that are using the platform or solution the most, and the ones that have great stories and examples to sell, and then kind of go by that. What do they look like before they came to us? Would they look like six months into implementation, 12 months, 18, whatever, and then try to go backwards. the approach that I'm talking about is a very narrow approach. So it's not.

necessarily scalable right away. It's what we've learned from this type of approach to scale our campaigns, scale our outreach, scale our nurture sequences. So we want to make sure that if we're selling six figure deals, that's our high end maybe. We want to look at what is that account that has closed at that and has all these characteristics that I just spoke about. And how can we kind of

target organizations that may be similar, but also we tell their relevant story. So we're not just telling the industry or persona story, we tell that account story. And then we can kind of scale back or scale that kind of approach and do it for like the one to few and one to many type of ABM approaches there are.

KK Anderson (09:37.659)

And so Define for me, I heard you say we tell the account story. So just for the person that's listening for our audience, just give a quick background on this whole concept of tier one, tier two, tier three, or one to many, one to few, one to one.

Kristina Jaramillo (09:54.014)

Okay. So to, yeah, yeah. One to many is more like demand gen in general, what people know demand gen to be. So you're basically trying to fill the pipeline. One to few is maybe they've engaged and they progressed a little further in their journey. So they're a little more relevant as you get further and further down. like from the one to many to one to few to one to one, you're getting more and more relevant. And one to one is I've heard people describe it as it has to be like an earned approach because

It requires a lot of attention. It requires a lot of input and resources. So it's basically for a one-to-one, you're learning what that account is, what is important to them as an account and how that trickles down. So what is the C-suite or what is the board saying at that account that's going to trickle down into the department that you're selling to? Like, how's that going to affect operations, customers, P &L, growth, anything that you can kind of tie your solution to?

And this type of approach again is for those bigger level accounts that we know are more, we've identified as part of our RCP, but we also know that they are more aligned with us. They have a strategic priority we can speak to and play a role in and just getting more and more relevant to them. So if you're targeting a bank, for instance, cause I have an example about this that I might get to later.

You want to tell the bank story, not a financial services story that has X amount of revenue, X amount of employees and customers, and X amount of locations. You want to tell that particular named bank account story. What's going on there? What are their initiatives for the next 12 to 18 months? What are they investing in? So are they more likely to be going into that digital transformation? Have they already done it? Where are they as an account?

And again, this approach is very labor intensive, but it reaps the benefits if it's one of those bigger deals. So this might not be, this approach I'm saying is not for every organization, but there are aspects of it that you can use it if you're selling a $25,000 solution or a hundred or multimillion dollar solution, hundred thousand.

KK Anderson (12:00.571)

Okay, so question. So when we think about enterprise accounts, we've got a lot of personas, a lot of different stakeholders that cross-functionally we may need to be selling to. So if you're doing that one-to-one approach, let's take your bank, for example, is there a number of stakeholders that you would market to? How do you adapt messaging and content based on your outreach strategy?

Kristina Jaramillo (12:31.278)

Well, when you redefine your ICP, so like if you're moving from a selling to mid market to enterprise, chances are your personas either change and if they don't change, it definitely expand. So I like to have at least three to five people engage and personas are going to change from even organization because we all know that everyone has different titles or different roles they play in every organization. So I would like to have a couple of people engage from influencer to if we can identify a decision maker or even a blocker or a challenger we can identify.

KK Anderson (12:48.741)

Yeah.

Kristina Jaramillo (13:01.08)

But we need to figure out what they typically look like and then the content that would be relevant to them. So if you're selling a solution, like a sales and marketing tech into an enterprise selling team, the AE is not going to have the same priorities as the CRO. So we want to make sure we're speaking to all those decision makers and all those influencers and speaking what's important to them, but what's important to them as a team. like the CRO is obviously going to care about things that are more tied to.

the business as a whole, team as a whole, whereas the AE might not, or even a director of sales might not. So we got to make sure that we're talking to their particular, like what's going to make them successful and how is your solution going to help them be better at their job? And also how is your solution better than competitors you've identified? Like where are the gaps and impacts in those competitors and where do you fit in better? Or how do you see those competitor gaps are going to impact?

the team and also, you know, in various ways, not just very in a revenue based way. And we need to make sure that we're speaking to that so that the team can make a decision and not get stuck in that indecision kind of like, it's a pain, but it's not a big enough pain for me. That means you haven't made that relevant connection. they could acknowledge it, but don't move forward.

KK Anderson (14:26.139)

Okay. And so that messaging, especially in that one-to-one approach, has got to be customized by person, super labor intensive. So what about in a one-to-few approach or a one-to-many approach? Because I would imagine that your campaigns kind of encompass all three levels. Is that right? So how do you, do you have to do hyper segmentation or something of your ICP?

Kristina Jaramillo (14:49.911)

Yeah, I mean,

Kristina Jaramillo (14:55.06)

Yes. And you also have to see if like an account, if it becomes more engaged, once they've entered the pipeline through maybe a one through too many campaign, if they become more engaged and you know that they have the potential to be a bigger value deal and there's more than maybe one person engaged and they've got attended webinars, they've downloaded assets, they maybe even replied to something and they have that potential to be a lucrative deal. That's how you can get them up to that one-to-one and whatever you're

like the content you're creating, the strategy and messaging you're creating for that particular one-to-one can be used to reengage similar accounts again in the one-to-many and one-to-few programs. So it's not a matter of all of the stuff that I'm talking about or all the strategy I'm talking about is just like for that one account. It can be used to kind of start that process all over again. And then once an account becomes like it hits a threshold of engagement and relevance and all it fits all these criteria's.

KK Anderson (15:51.483)

Mm-hmm.

Kristina Jaramillo (15:53.89)

then you can be know that's when it's time to really dive in. And it has to, there has to be so many signals from not just intense signals when I say signals before you develop that, because again, it's labor intensive and you don't want to waste time on something you know is or you can tell that's not going to move forward.

KK Anderson (15:57.691)

to really dive in.

KK Anderson (16:15.141)

So just curious, would you, let's say the signals are hitting and you decide to pull them out of a one to few campaign and upgrade them to a one to one, are you gonna engage in AE at that point or are you still with the BDR?

Kristina Jaramillo (16:30.798)

it depends on how much the BDRA might've already engaged with them. If they've already engaged, then we'd continue with them, but most likely because they're the bigger deals. They usually go to higher level salespeople and more experienced or they might, might be a team kind of thing because it, depending on how many insights there are from, who's engaged with them in their journey.

KK Anderson (16:43.237)

Mm-hmm.

KK Anderson (16:53.211)

Okay, let's move on to the next topic, which is fixing flawed ABM programs. This is one of my favorite conversations because it just seems like every single day, know, do you remember the book, Who Moved My Cheese? I'm dating myself right now, but.

Kristina Jaramillo (17:04.867)

Me too.

Kristina Jaramillo (17:10.77)

Yes. I remember seeing that title. No, you're not because I remember actually, well, I remember seeing it and my dad brought it home when I was like in college and was like, this is a weird title for a business book. And then he explained it to me. was like,

KK Anderson (17:23.267)

It's so good and I feel like our cheese is moving every day in sales and marketing, go to market strategy world. So, you you've worked with companies who've invested in all kinds of platforms like a sixth sense or demand base and different intent platforms and they're not seeing ROI. Like what's usually missing?

Kristina Jaramillo (17:48.024)

So it's interesting, I've talked to dozens of companies that are using these type of platforms or have used them in the past. And there's a handful that are always the same players that are coming in. One is it that they've relied on the ICP proxies within the platform, which again is not the ICP, it's at total relevant market. So it's too broad, it's not focused enough. Another one that's really...

a key player in having this not be as successful is there's a lack of change management. So if you have the wrong email, social live, even digital interactions and deliver those wrong account experiences, you're not going to convert it in market opportunity to revenue no matter how much intent the account shows. But a lot of people do that. And I've seen that there's churn rate issues or churn issues at these companies because they're not giving

A lot of the teams at these organizations aren't giving their customers the advice to be ready before they purchase this solution. And these are hefty investments. They're not cheap. And then these accounts are not converting. They're letting the tech drive the strategy versus having the tech support the strategy. So that is a big problem. And they just didn't do that readiness before they even adopted the platform to see if they were even in the right frame of mind to identify

you know, where the reds were in the business. Are they having a churn rate? Are they having a pipeline issue? Are they having an issue with accounts going dark or whatever disengaging? Another issue that I see with these platforms is that people are getting limited account insights. So the platform can identify the accounts, you know, that you might want to engage in. There's no guidance to what the intent was, why it was there in the first place.

what was the reason for it. So they don't understand necessarily the context behind the intent and why, you know, what's going on. There's no real direction to engage those accounts. Instead of telling an account story, we're going back to those persona and industry stories, just like your competitors. So we're all reacting the same way to the intent. So then if an account becomes unresponsive or goes dark, we kind of figure we're left wondering why and it's because we didn't

Kristina Jaramillo (20:12.056)

do the due diligence. Obviously you can't do that with every account, but the biggest, another big issue that I see is that a lot of teams aren't providing the account-based enablement to bridge the intent that's coming in to have, so no sales knows what to do with it. I've seen a lot of marketers telling me that, you know, we have six cents, we love it, but marketing or sales hates it. And it's because sales teams aren't equipped with the insights or the enablement to continue that conversation that marketing has started or engaged.

So they're being just again, going back to that handoff and there's no tools or messaging or stories so that sales can become multi-threaded. They don't have specific business cases to talk about. They don't have the tools to create that consensus and overcome that indecisiveness and move accounts to revenue. So there is that problem where one team might really like it and then the other team doesn't. It's because they're not equipping the team to maximize the platform and the results from it.

KK Anderson (21:11.003)

And then I imagine what happens is the unequipped seller probably then gets on the phone and just starts feature jumping. Let me demo, let me talk about our product, here's what we do, here's the problems we solve. And they may get some nodding heads and some, that's cool, but they're definitely not building the urgency.

Kristina Jaramillo (21:25.742)

Yeah.

Kristina Jaramillo (21:32.236)

Yeah. And so all that hard work that marketing did sales kind of backpedaled for them, but not because they want, you know, they wanted to, it's because they didn't have the resources and they didn't know what to do next. So they had an account that maybe was a little warmer and that they had been equipped with this insights or this knowledge up. They would have been able to address the conversation completely differently.

KK Anderson (21:55.205)

So do you have a preference for what type of platform or program that you recommend for these kinds of things? is that intent signal, mean, is that cheese moving as well, should I say? Like is that still as effective as it used to be?

Kristina Jaramillo (22:17.868)

don't think so only because so many people have it now. Before when it was like new and you were the only one or a handful of people that had it, it was one thing. But I know more platforms are telling you who the actual person is with the intent, but just telling me that a company, like if you give me that there's intent at Microsoft, doesn't mean what am I, how am I going to handle that one? There are some that are getting down to the person itself, which is very scary to me, but it's

KK Anderson (22:35.003)

Yeah, that's impossible.

Kristina Jaramillo (22:46.442)

It's more to me that it's become targeted to man gen. So you're doing demand gen, but you're doing it at a middle, more relevant, a little more targeted, but it's still a narrower spray and pray. It's useful. It's just not being used. And I don't think that a lot of companies can justify the ROI from it when it comes in terms of revenue as opposed to like, unless they're targeting or if they're

KK Anderson (22:59.675)

Mm-hmm.

Kristina Jaramillo (23:14.648)

keeping track of MQLs and MQAs and that's how they're justifying the spend. But if they actually turned and said, this particular tool in Sixth Sense or demand base led to X amount of revenue, I think it's very hard to justify the expense. We saw people that tech last or maybe like your three quarters away there and then you adopt a smaller part of the tech and then you grow from there. But if you do it first, you're going to have that tech for like six months before you've actually built what's go into it.

KK Anderson (23:28.431)

Wow, yep.

KK Anderson (23:44.365)

Or before you even know, like if you start using it and it's not working and you you've got the common pitfalls like you were just describing, you may not even know. So I've heard you say that ABM should influence revenue and not just generate MQLs. And you've talked a little bit about this already, but what are those like right metrics? Like what should...

Kristina Jaramillo (23:44.749)

So why do.

Kristina Jaramillo (23:53.142)

It's not the tool. Yeah, it's not the tool. It's the way it's being used.

KK Anderson (24:12.749)

marketers be looking at not just for ABM success, in general.

Kristina Jaramillo (24:17.506)

Yeah, so NRR is your ultimate metric. We want to look across that buyer's journey and customer lifecycle and impact stage progression, win rates, deal sizes, ARR, GRR, again, ultimately that NRR. So we are marketers in our organization, in our firm, but we really are focused on revenue as well. So we're assessing that go-to market. We want to look for what's happening. Where are we losing? Why are we losing?

We want to see if we're getting that VP and C suite engagement, because if not, then we need to build metrics around that. why not? Are we getting engagement across the organization or is it just the one department? And put metrics around that. It might not be relevant to your whatever you're selling, but a lot of times it is. are we looking at the lagging revenue indicators like stage progression, win rates, deal sizes?

and AR, GR, and NR and putting measurements around those to see where that business problem lies. So when we engage as a forum with people, we want to look at the biggest red in the business and address that first and develop the strategy from there and then move on to develop or to develop strategies for other areas that are revenue leaks.

KK Anderson (25:31.579)

So, kind of spilling into the topic of what's not working anymore in B2B marketing, I'm curious, how have your different channels shifted? Are you less on email, more on other channels? What are those kind of, how are you building up your intent signals?

Kristina Jaramillo (25:57.945)

From our firm, I'd say we're more on LinkedIn than we are on email. I'm seeing a lot for our customers as well because you can engage with your buyers in a different way. You can see what's important to them. What are they talking about? Why are they talking about these things? What is, and I'm not saying like personal, like they went to Penn State. I'm talking like, what are they doing in their role and how is it?

KK Anderson (26:01.859)

Okay, tell me about that.

KK Anderson (26:23.269)

Yeah.

Kristina Jaramillo (26:24.736)

How is the market impacted? How are the tools they might using be impacted? What they're doing and how they're achieving them. So you can do a lot of homework before reaching out to someone and knowing a little bit more about them before you send them that LinkedIn message or an email message, or you decide to call them however you're outreaching to them. And I think the same thing is happening for our clients is that they're using and market in general, that they're using LinkedIn, they're using these other tools and other platforms to see what's going on with that individual first.

So they can get relevant beyond you live in Phoenix or you went to XYZ University or you're working in this industry. I wanna get more insights the better and LinkedIn is one of those platforms that is like a plethora of information. And you could even see what the person might be writing on about or commenting on or things like that. So you get an insight into how they work and how their team might work.

KK Anderson (27:18.843)

How do you do that at scale?

Kristina Jaramillo (27:22.06)

That at scale can be hard, but BDRs can definitely like say if BDRs are working on your one to many or one to few, they can use Navigator. They can use regular LinkedIn subscriptions and do a little bit of homework before. And again, digging deeper, like they have to be told and taught to dig deeper than those generic similarities. What might be bad? What's influencing them on their day to day and how can what you're selling or

KK Anderson (27:43.226)

Right.

Kristina Jaramillo (27:50.094)

How can your solutions or your platform, how can it help them be more successful? And you got to position it that way versus, you know, I know that you're in this industry and we've seen a lot of people in this industry have this problem.

KK Anderson (28:02.607)

Right, it's almost the exact same thing you were just saying with the one-to-one in an enterprise account. Like it's not good enough to have just that market story. You have to have the account story.

Kristina Jaramillo (28:14.7)

the account story. Yeah, I mean, when's the last time anyone closed a six or seven figure deal with just sending generic thought leadership or industry leadership? I mean, it might, but yeah.

KK Anderson (28:22.147)

Yeah, it's probably been a long time. So it's a LinkedIn connection and then a LinkedIn message is another way that you're doing it. What else? Are there any other like intent channels that you've been seeing that work in getting engagement with enterprise just primarily? I mean, are you using email still?

Kristina Jaramillo (28:44.302)

Kristina Jaramillo (28:49.272)

I am, but it's very like compared to what it was. I do LinkedIn first. If I get engagement versus like say I reach out to someone that I know would be a great fit because we have a business case, we have a case study, we know what's going on strategically. We did all our homework. They engage with me by connecting because I'm sending them a relevant message. And then I send them, I might send them up a couple of weeks later, another follow up message to.

KK Anderson (28:52.667)

Tell me about that.

Kristina Jaramillo (29:15.362)

read a certain article and they don't engage with that because the LinkedIn inbox can sometimes be a black hole. Things just get lost in there. Then I might try to find their actual email address and try to reach out to them that way. And then maybe send one or two followups to nurture them that way. email is always like my last resort only because it's not, I feel like it's intrusive, number one, like you're getting to the person's inbox that they basically live in.

and you haven't necessarily earned the right to get there. And I don't want them to think that I'm just another person selling something. Like I have to, if I'm outreach with them, I'm, there's a reason. So there's a reason is I have information to share that's relevant and I have content to share. I'm not just saying, let's jump on a call because I know that I get dozens of those a day and I ignore all of them. So it's definitely happening at the enterprise level. So I always say people, if you're going to...

reach out to someone, whether that's on LinkedIn, whether that's email, however you decide to engage with them, there has to be a reason. Like it's not just that you want to sell them. That's not the reason. It's because I know that XYZ is happening at your company and this article will explain how to address it or how to be proactive so it doesn't happen to you as well. So you're giving them value and it goes back to value selling. And that has to be something that marketers, like I think that's a lot of a big problem with this is that a lot of marketers are not.

educated in the ways of selling. And that's why there's such a disconnect because they just think of marketing in those very brand awareness type terms as opposed to, well, what's going to move that revenue needle forward? Like does a salesperson, would they care about the features and benefit article to share to their, their prospects? Most likely not. Cause it's not as successful for them. So I think when you're in the sales,

Like you put on a sales hat or you walk in their shoes or you listen to a sales call, you understand them so much better and you can write for them better. You can produce content and produce assets for them so much better when you know where they're coming from and you speak their language.

KK Anderson (31:20.987)

Yeah, I was just about to say you're speaking my love language.

Kristina Jaramillo (31:26.446)

You have to, if you want them to be successful and you want them to work with you in a consistent basis, you have to speak their love language, which is revenue. Like it's not.

KK Anderson (31:35.301)

Right, right, exactly. But as a sales leader and sales coach myself for decades now, I find myself saying probably on a daily basis, like it's serve over sell. And I don't care if you're selling a metal valve or you're selling a seven figure SaaS product, right? It does not matter.

If you want to differentiate in today's market, you must serve over sell. If you're not helping them solve a business problem, if you're not consulting with them on how to advance their career, what's in it for them, you're not going to get anywhere. Right? And so it is, how can you help them?

Kristina Jaramillo (32:26.882)

Yeah, how do you want to be perceived too? Do you want to be perceived as a partner or a vendor? And marketing has to think about that too. And I think that's the best.

KK Anderson (32:29.787)

That's right. You want to be a And it's almost like, how can you get them to say thank you? Like, wow, that was nice. Right? And so when you're coming into their inbox, you you want to do that. That makes it a lot more tricky. I'm curious to get your take on cold calling and having BDRs pick up the phone and call people. I, you know, obviously you want to do that with a serve.

Kristina Jaramillo (32:39.937)

Mm-hmm.

KK Anderson (32:58.051)

over sell mentality as well. But talk to me about, I know we're going a little bit off track here, but how you combine your call with your LinkedIn, with your email and your approach to really try to deliver some value.

Kristina Jaramillo (33:15.648)

Yeah, so I am the last person you want to talk to about cold calling. But if you were to have, like say you have a set number of accounts or whatever and you're trying to outreach to them, again, are you calling to hit your number of calls for that day or are you calling to actually engage with someone? So I am always quality over quantity. And again, if you're not teaching, even in that, even if you're doing a cold call, if you're not trying to teach them or say, you know, page three of this, you know, executive

brief that's 50 pages and really long is really where you should focus. You might not need to read the whole thing, but definitely page three you need to focus on because it's got X, Y, and Z in it is way more beneficial and interesting to me than saying, here's a 50 page report. Get to like, good luck. Add that to your list of reading for the day, evening. And it's, it's, it tells them that you read it too. And you know about it and you're more in a

KK Anderson (33:59.695)

Yeah!

Kristina Jaramillo (34:14.146)

well-read on their industry and what's going on with them. And then you even took the time to pinpoint something that they should care about and why. Totally different conversation than saying, you know, here my product and feature dump and this is why we're better than XYZ competitor.

KK Anderson (34:25.807)

Right. You have to earn the right to be able to talk about yourself. Right? Yeah.

Kristina Jaramillo (34:31.326)

Absolutely. Yep. A lot of sellers know this, but marketing needs to get on board too.

KK Anderson (34:36.091)

That's true. So, okay, so if you're, you know, for the CMOs out there in the audience that are listening right now and, you know, kind of steering back to the ABM concept of this one-to-one, then one-to-few and one-to-many, you know, marketing, like what should they be thinking about when starting and executing an ABM program to go up market to enterprises?

Kristina Jaramillo (35:07.64)

So right now I would really focus on building the right foundation to change those interactions that the teams are delivering and how the experiences are being delivered, how the account experience is being delivered versus what I see a lot of people doing and then have their ABM program fail and then wonder why. Is there retrofitting ABM on top of what they're already doing and just using it to source the pipeline?

And ABM can be used to sort the pipeline, but it's not as effective as it is to actually driving change with the accounts, moving those accounts forward and driving revenue. So I have an example of this. I recently spoke to head of marketing and an AP and automation FBA FPNA tech. So they wanted to see how they could fix their ABM program. They had started it eight months ago, so it was relatively new.

What they really needed to do is recalibrate what they were doing. Their frameworks needed to change, their processes, their metrics. They had done this retrofitting of what they were already doing and they were not seeing the ABM returns and the time and investment. So we noticed it was that they were putting ABM just on new logo acquisition, which you can, but it's much more difficult to do versus reviewing that go-to market like we've been talking about.

and they were also defining their ICP with generic things. So a generic trait. So for them, it was like how many transactions they had, you know, what did their, you know, platform look like? What did their ERP environment look like? They were not segmenting their existing customers to see where they had the greatest long-term revenue with those kinds of customers. And then looking at them.

to see how they could get similar characteristics beyond those demographics and technographics so they could better define their ICP. They hadn't redefined it or readdressed their ICP. So these are things that people really need to do before they develop an ABM program in order to make sure that it's successful. Otherwise, you're looking at maybe six months, maybe less before you're like, it's not working. We're gonna leave it.

KK Anderson (37:23.137)

You said something that I want to, I want you to double click on for me, Christina. You said maybe they're using it on net new acquisition versus their install base is what I'm, what I'm assuming. Tell me more about.

Kristina Jaramillo (37:37.612)

So for us, what we've seen the most success and what I've seen other people even say this is that ABM really has success, greater success on retention expansion than it does on net new. Because to me, net new, a lot of it has to do with demand. So if we are, we know there's a dozen accounts that are up for renewal and we need to know this ahead of time, not 30 days before renewal.

KK Anderson (38:04.987)

You

Kristina Jaramillo (38:07.118)

because you can't throw together a strategy that quick. They're renewing and they have a potential to expand because they've been using us on a weekly or monthly basis versus an account that's only been using us on a quarterly or annual basis. Then we need to know what we need to do to address the stay, why stay, why now conversation and why expand. Like this is what you look like when you came to us, this is what's happened since you've worked with us and this is where we see opportunities in the next...

know, six months to a year, however your contracts are situated, areas for growth. So you're again, going back to that, seeing as being seen as a partner to grow their business, as opposed to just a vendor of a solution. And you can expand that account, maybe either they can have different features or different solutions that you offer, they can add on to what they're already buying, or maybe they have business units that you need to break into and they can help you kind of break those walls down. So it's all a matter of

trying to get these accounts to grow and stay with you, then land and expand. It's doable on land, excuse me, land that new. It's just a longer road. And I think people don't think of it and they think, ABM will just fix all my problems and we'll land that new within 30 days.

KK Anderson (39:07.739)

Come on.

KK Anderson (39:21.881)

Yeah, and why is it that it takes longer with the NetNew?

Kristina Jaramillo (39:27.626)

It's similar to the fact that you need to do all your homework on an account that's net new versus if they're a customer, you have most of that done for you already. Usually what's harder enterprise-wise, same thing with ABM like normal sellers have.

KK Anderson (39:31.493)

Yeah.

Yep, got it, okay.

KK Anderson (39:43.323)

Okay, well that is some great advice for our CMOs listening. Let's shift over to, I'm having so much fun talking, I'm losing track of time. Let's shift over to, and we've talked a little bit about this, but that marketing to sales handshake, right? Really closing the gap between the two. What does that look like in practice?

Some may say you get an MQL, you hand it over to sales and then they're off. You've talked a little bit about this, but how do we really make that overlap?

Kristina Jaramillo (40:24.558)

So basically means you're not just working accounts to pipeline on the marketing side and giving sales that intent, the engagement, and then sitting back and waiting for them to tell you what they think they might need or what they need based on that selling cycle. You're proactively working to influence the selling conversation on the marketing side. As a marketer, I'm providing account insights that sales need to have that right engagement. We're providing them with content to support them, to help them reframe conversations content to...

support them once, you know, if they've celebrated through the selling cycle and now it's just internal conversations, what kind of content am I, supporting them with so that they can be, have these conversations internally and, and go in our favor. Are we providing with stories on the reframes they need? Want to make sure that they're also providing account based value props, conversational support.

We're helping sales enable buyers to make that trade off between what they're doing now and working with you, justify the business case and have that confidence to make a decision that's going to drive change. Cause obviously change is very scary. It can be expensive. It can be timely. We're helping sales overcome those issues with these prospects and bring those different buyers together. And we're helping sales address those struggles that they're dealing with within particular.

So we've already either they've seen them before so we know how to enable them or there's something new and we need to learn how to enable them. So we're thinking of working alongside sales and account teams until it's revenue or there's greater revenue growth. It's all about making marketing accountable for revenue just like making sales teams accountable. It's obviously not going to be the same numbers and the same metrics and things like that, but all teams should really be accountable because an account based approach

really should be joint sales and marketing and a CS win. I know it's account-based marketing, but I like to say account-based go-to market instead because it makes everybody accountable as opposed to just one team. it's, especially in this day and age, it's very hard for just sales to do everything alone. It's virtually impossible.

KK Anderson (42:29.167)

No.

KK Anderson (42:39.887)

Right, that's really interesting. I like that account-based go-to-market. Yeah. So how often are you recommending that sellers should be meeting with their marketing team?

Kristina Jaramillo (42:58.522)

so depending on how you're structured, say someone who's the, the ideal idea would be that there's a marketer aligned with segments of the sales team. And I would say like ideally weekly, but if not at least monthly, so we can see like, where are these deals stuck? Are they progressing? Do you need additional support? Do we need to have, do we need to create a webinar content or a case study based on what you're having a problem you're having? Because we've seen it two, three, four times already.

So obviously this is something we need to address as a company or as a team. So you can check in because if you're just kicking them over the fence and just hoping something happens and then waiting to the end of the quarter to see what's going on, it's too late. It's really too late.

KK Anderson (43:39.183)

Right. That is such a great point. That is such a great point. Okay. So let's see. When you think about, you know, just last week, I don't know when it dropped on our podcast schedule, but I think it was last week, we had an interview with Cathy Minter, who she used to be a co-host of Selling the Cloud, and she was our guest last week. And she talked a lot about a unified CRO model where

marketing, sales, customer success, a lot of what you just said. Like it's interesting how all of these conversations are all happening at the same time. Like it's so important that everyone is unified under one kind of leadership. And so, you know, I know this is kind of putting you on the spot, but like what's your perspective on that? So if you have one, let's say your chief revenue officer and you've got marketing, you've got everyone in the revenue organization is kind of reporting up. Like what's your perspective on

or do you feel like they should all be separate?

Kristina Jaramillo (44:40.782)

So if you have a CRO and everyone's reporting the CRO and not necessarily a CMO, that automatically means that you should be focused on revenue. But ideally, I like it so that the BDRs are under marketing. Because then it's almost like marketing gets to train them on what they need to ask for to support. And then we can know how the higher level business development or sales team needs, what they're going to need.

KK Anderson (44:55.855)

Okay.

Kristina Jaramillo (45:09.274)

In a perfect world to me, there would be a CRO and a CMO and they're in lockstep about how they're going to hit the revenue goals together. And they're constantly meeting because then that trickles down to their respective teams of how we're going to work together. Because if you see them align, then it's much easier for the teams to come together. But if they're not working together to hit these revenue goals, that's where that misalignment happens. That's where I'm going to give you MQLs and then hope for the best at the end of the quarter, of the year.

KK Anderson (45:21.871)

Mm-hmm.

KK Anderson (45:35.794)

huh.

Kristina Jaramillo (45:37.454)

So I think it's all a matter of that changement internally, change management.

KK Anderson (45:40.997)

So any kind of stories or experiences that you've had where either there's been a really strong handshake or where there's been a gap and that alignment story is so interesting to me because I feel like that is an obvious gap for so many people that are listening. For one, just to say like a CMO typically has real data. They've got numbers, they've got all kinds of data that they're looking at.

And a CRO, unless they're using like a platform like Collective Eye or something, they don't. have, well, don't, know, our seller says this deal is going to get pushed because of this or that, or, know, it's all, you know, it's all speculation and opinion. so, you know, that causes a lot of consternation a lot of times between CMOs and CROs and to their CEO, right? So just anything comes to mind as far as, you know,

Kristina Jaramillo (46:22.286)

So big, right.

KK Anderson (46:40.805)

clients that have done this really well or...

Kristina Jaramillo (46:45.962)

Yeah, it's, it's when there is like, if we go into an organization and the sales and marketing leaders are not on the same page or we don't have access to one or another, we already know that our success rate is going down. we've worked with organizations where they will keep us completely siloed from sales. So we've developed great content. They've been engaged, they've engaged with it in campaigns, but we don't know what's happening after that because they are so siloed internally that

we cannot get past them. So those clients don't wind up being a great fit for us because we want to make sure that we're impacting revenue and there's no way for us to know we are. Like they've engaged with content from us, but we don't know what happens after that. So it's very hard when there's not both. ideally for us, we come in where there's alignment or we come in and we work directly with the selling team and we're working with the VP, senior VP of sales or the CRO because we're creating that

strategy and content and messaging for the selling conversations that he knows his team's already having, but they just can't get that level of attention from marketing because they were either not on the same page when it comes to that, because they're more brand awareness and they're more metrics on campaigns. Don't have the manpower because it is like, as we've been talking about, what we do is very time consuming. But if you can, if this, let's say

program I'm running, takes me three months and I close a six figure deal, then it's worth it. Because then we can try to replicate that or we can try to influence the smaller deals. And then we can give a lot of this information to marketing so that they can optimize the programs they're running. So it's, it's very hard if there isn't that change management. And I've heard, I've talked to a lot of people that are in marketing that they want to do all these great things, but there is no senior leadership alignment, but they want the results. The senior leadership wants the result, but there isn't that alignment.

And they say they're aligned, they're not really, in theory they are, but not, they're not orchestrating and moving as one team. So like an ideal role, the CRO and a CMO would be best friends.

KK Anderson (48:53.467)

Yep, 100%. Okay, so let's move on to, excuse me, rapid fire questions. This is my favorite part of every episode. And Christina, what we like to do is just ask some quick questions and you can give us your knee jerk reaction. Okay, what was, well, let me see, every good marketer has to have sold something at some point. What was the first product or service you ever sold?

Kristina Jaramillo (49:11.864)

Got it.

Kristina Jaramillo (49:23.086)

So if we wanna go back to like the original original, I would say Girl Scout Cookies.

KK Anderson (49:26.427)

There you go. Door to door.

Kristina Jaramillo (49:28.694)

Yeah, but then after, yeah, well then after that, yeah, well actually I even my dad, I even got my dad in on it. He would bring in, this was back when they actually had paper forms and you put your name and like checked how many you wanted, like a thinment. He would bring the form in to work and we lived in New Jersey, but he worked in New York. So he would take the train, bring the form in, he'd come back and he'd sell like hundred cookies or boxes. And then he'd have to come in for like three or four days, a couple of weeks later with duffel bags.

Anything for like a reward.

KK Anderson (49:58.659)

So you are delegating very early. You were an entrepreneur even then.

Kristina Jaramillo (50:04.558)

It helps that my dad and I are very close.

KK Anderson (50:06.797)

I love that. Okay, who's your favorite CMO or go-to-market strategist to follow?

Kristina Jaramillo (50:14.742)

Yeah, so he was a CMO, believe he was. Yeah, he was CMO, but he's a go-to market strategist now Sangram Vahri at go-to market partners. He's one of my favorite because he tells it like it is and it's no sugar coating it. And he's telling you, you don't have a sales problem, you don't have a marketing problem, you don't have a customer success problem, you have a go-to market problem. And a lot of the content that he and his team shares is very relevant. So if you're not following him, I suggest it.

KK Anderson (50:38.651)

That's really great. then, I should say, Christina, you and your partner produce some amazing content as well.

Kristina Jaramillo (50:45.826)

thank you. We're very busy.

KK Anderson (50:46.795)

Yes, some amazing content. So definitely go follow their newsletter and then you also have a podcast.

Kristina Jaramillo (50:55.478)

I do, we do have a podcast. You're going to be on it, I believe next week.

KK Anderson (50:58.048)

Yes. And tell us what's the, tell us about the podcast and where they can find it.

Kristina Jaramillo (51:03.34)

Yeah, it's on every platform wherever you listen to. I just happen to be a Spotify person, but it's called the ABM Done Right. And we talk to people who have both sides of the fence. So sales and marketing leaders that are typically in the tech and SaaS industry, and they're selling complex solutions. So they know all the things that we've been talking about. And they really just want to optimize their programs. And they're telling you lessons learned, what works, what's not working.

why they recommend certain platforms and certain strategies and people will tell you like the honest answer of, know, we adopted ABM before we ready or we, you know, adopted ABM and then ran it for three months and didn't give it a chance. And so that we have to start again. So it's, it's, I learned a lot and it's a, I nerd out a lot with people that I don't necessarily get to talk to otherwise. So it's, it's something fun.

KK Anderson (51:51.555)

Yeah. Okay, so what is a leadership or go to market practice that you think every sales or marketing leadership adopt?

Kristina Jaramillo (52:01.986)

So I think a lot of people need to focus on their why. Why are we running this campaign? Why are we reaching out to this company? And if you can't figure out the why, then maybe you need to go back to the drawing board. Or why am I picking up this phone or sending this email? Because I think a lot of people are just focused on the tasks they need to do, that they get stuck so much in the weeds of the tasks that they forget the strategic part and the strategic reason we do all these things.

KK Anderson (52:30.235)

Start with Y. Start with Y. Okay, advice you'd give your 21 year old self.

Kristina Jaramillo (52:37.07)

Um, let's see advice to give my 21 year old self would definitely be to travel more. I definitely traveled more in my twenties, but I should have traveled even more internationally. And I would say if you have a passion that you want to follow, that's the time to do it. I mean, you can do it in your forties and fifties and sixties and beyond. It's just harder. So if I had, if you had something that we're passionate about at that time, other than traveling, that was what I was passionate about. It probably would have gone down a different road.

KK Anderson (52:55.483)

So much fun.

KK Anderson (53:02.987)

Yeah, really, really great advice. I have a 20-something year old niece, two of them nieces, they're both in Italy right now and I'm thinking to myself, God, I haven't been there since I was in my 20s.

Kristina Jaramillo (53:15.382)

same feeling I love it on.

KK Anderson (53:17.499)

Okay, last one. What's your favorite business book? What would you recommend to your readers for, to our audience for a good read?

Kristina Jaramillo (53:26.38)

So I know you said business book, I'm a really big, I'm a nerd because we always focus on the go-to market. I'm reading a lot of only sales marketing based or go to meet, go to market books. So my top two, would say would be the challenger sale, which people I should, if you haven't heard about it, Google and look it up. And my favorite, there's a couple of different challenger ones, but the challenger customer, cause you kind of get inside the head of what the customer is thinking and then it can makes you a better marketer.

And it sounds like it would be more of a seller's book, but it totally is for both sides of the team.

KK Anderson (54:01.614)

the challenger customer.

Kristina Jaramillo (54:03.936)

and the jilt effect that's written by some of the authors from... Yeah, it's a good one.

KK Anderson (54:05.657)

yes, I've read that one. Yeah, that is an awesome book. Okay, awesome. Well, Christina, thank you so much for joining us today. And we will include all of your recommendations in the show notes and then also your LinkedIn profile and a link to your podcast as well. Yeah, it was a lot of fun. Okay, talk soon.

Kristina Jaramillo (54:21.666)

Thank you so much. really appreciate it.

Kristina Jaramillo (54:31.79)

All right.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Kristina Jaramillo, President of Personal ABM, joins KK Anderson to unpack why most ABM programs fall short; and what it really takes to win and expand six- to seven-figure enterprise accounts.

Kristina shares how B2B teams can go beyond persona-based playbooks to deliver personalized, strategic account experiences. She explains how to redefine your ICP, align marketing and sales with shared revenue accountability, and build campaigns that influence real pipeline movement; especially when targeting enterprise buyers.

What You’ll Learn:

• ABM Foundations that Win: How true account insights—beyond intent data or personas—unlock six- and seven-figure deals.
• Strategic ICP Redefinition: Mapping accounts by strategic readiness and revenue potential, not just firmographics.
• Full-Funnel Alignment: Tactics that unite sales, marketing, and CS around shared expansion and retention goals.
• Personalization at Scale: Frameworks for moving from one-to-one to one-to-few without losing relevance.
• Revenue-Centric Metrics: Using stage progression, influenced pipeline, and NRR to prove ABM impact.

Key Topics:

• Strategic account-based marketing for mid-market & enterprise growth
• Differentiating ABM from demand gen
• Intent data traps and tech misuse
• Metrics that go beyond MQLs: NRR, stage progression, deal influence
• Aligning CS, sales, and marketing around buyer relevance
• Orchestrating account experiences, not just sourcing leads

Guest Spotlight: Kristina Jaramillo

Kristina is President of Personal ABM and host of the ABM Done Right podcast. With a deep focus on revenue-driven marketing, she helps B2B tech and SaaS companies build customized go-to-market motions that win and expand high-value enterprise accounts. 

Resources & Mentions:

• Podcast: ABM Done Right
• Go-to-market strategist to follow: Sangram Vajre
• Recommended Books:
• The Challenger Sale
• The Challenger Customer
• The JOLT Effect

🎧 Listen now and follow Selling the Cloud for more GTM insights from leading voices in enterprise growth. Subscribe wherever you get your podcasts.

KK Anderson (00:01.573)

Hello and welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Christina Jaramillo, president of Personal ABM. Christina is a trailblazer in strategic account marketing. Her firm specializes in helping tech and SaaS companies evolve their go-to-market strategies to land and expand six and seven figure enterprise accounts. Unlike

many ABM programs focused on automation and intent signals, Christina's approach centers on creating highly relevant one-to-one experiences that influence every stage of the buying journey and drive real revenue outcomes. And so today, Christina is going to share with us what it really takes to succeed in the enterprise space, especially for mid-market companies trying to move up market.

So today we're gonna explore four themes with Christina. First, we'll talk about redefining your ideal customer profile, your ICP, and enterprise buyer personas. And we'll talk about how do you align that? Your targeting, your messaging, and how do you get that message right with enterprise priorities? Second, we're gonna talk about fixing flawed ABM programs.

Why are so many intent-based, persona-based, ABN programs failing? And how can you rebuild them around account-specific insights and business cases? Third, we're gonna talk about what's not working anymore in B2B marketing. Okay, spray and pray email sequences, generic content, we all know it's no longer cutting it. So we're gonna talk about things that we can do instead. And then finally, fourth,

We're gonna talk about turning the marketing to sales handoff, turning the marketing to sales handoff into a handshake. We all know that there's usually some kind of an island or a gap between marketing and sales. And the real trick is closing that gap. And Christina is gonna talk to us about how we can support that handshake. This episode is packed with practical insights for revenue leaders looking to break into larger accounts.

KK Anderson (02:21.889)

improve win rates, and align sales and marketing. Let's dive in. Welcome, Christina, to Selling the Cloud.

Kristina Jaramillo (02:29.602)

Thank you so much for having me. I'm looking forward to the conversation.

KK Anderson (02:32.077)

Yes, we are so excited that you are here today. So let's jump into the first topic, which is redefining your ICP and your enterprise buyer personas. And you've said in our conversations that so many companies that are trying to move up market fail to really, truly redefine their ideal customer profile. So start with.

maybe describing what's the difference between an ICP when you're targeting a mid-market buyer or an enterprise buyer.

Kristina Jaramillo (03:08.344)

Yeah. So first off, I'm going to say that most companies don't necessarily have a ICP in the first place. They might have an ideal customer segments or a total relevant market, which is has sales and marketing teams guessing where they should be prioritizing accounts, where they should be focusing on. So your ICP is your ideal customer. So they're the ones that should be the ones that are predictive of accounts landing, expanding with you, because they align with you. They're going to align with you in a couple of ways. It's operationally.

executionally and culturally. These are the ones that are strategically ready for your solution as well and ready to implement with success. They're the ones that have a key strategic priority in place that your solution, your platform, whatever you're selling can play a role in. So no matter how much pain you solve, an enterprise is really not going to move forward with a deal if it doesn't fit into their existing strategic priorities.

These are the ones that you have a differentiated situational story to tell. So we all know enterprise deals are inherently longer and they're getting longer, you know, currently, and they're more complex. They require more time, more resources and focus. So you don't want to be wasting your time and your team's time on accounts that are most likely not going to move forward or they're going to get stuck in indecision or churn after a deal is closed. So it's really important that we redefine our ICP and keep optimizing that ICP.

because the market changes, your business changes, your customers and your focus changes. So your ICP definition is really going to make sure that you are winning or losing deals and how accounts enter or leave the pipeline. So traditionally, I still see a lot of organizations focusing their enterprise ICP on pretty generic broad.

So like industry, company size, revenue, technographics, maybe a superficial look alike. So I've seen stats saying that when you do things like that, you're cutting your win rate by at least 60%. I've seen even closer to 70. And while companies, I know it's kind of scary, but while companies are building their pipeline with these enterprise accounts, win weights are dropping. And it's a lot because companies are spending time on enterprises that...

Kristina Jaramillo (05:28.95)

are not likely to land and if they do, they might turn. And if they land, they might not ever expand. So account-based go-to market, which we specialize in, is about aligning that complete marketing function with sales, with customer success, so that we focus on the ICP as a team versus just that total relevant market, which is what a lot of companies I've seen have focused on. The ICP that you focus on are the accounts that are predictive of landing and expanding with you.

So we need to focus on what are those characteristics of those key enterprises? What are characteristics of enterprises that are strategically ready for you? So for example, most companies are not yet structured to succeed with AI. They might want to move forward. They might be very interested. They might be looking, but they're not set up if they bought an AI solution to maybe use it to its full potential. So there's a risk return, even though there could be greater success.

So what we really need to think about is where are we relevant, where our competitors are relevant, and then think about the strategic priorities where we should be looking for in a prospect. And then the situations where we have that differentiated situational story to tell. So it requires more work and it's not something that just kind of sits in a pitch deck somewhere or in a slide somewhere, it never gets revamped.

KK Anderson (06:53.093)

Wow, that's quite a lot. So...

you know, as you are shifting and, and I guess it's way more than just segmenting is what I'm hearing you say. Right. It's more around the strategic priorities. And so, so like, what are some of those blind spots that companies have?

Kristina Jaramillo (07:07.47)

Yes, that's why we need to be real.

Kristina Jaramillo (07:17.656)

think they either let marketing define it or let sales define it, or they each have their own version of it. And there's, it's not like a cohesive one that you should be able to ask someone in both sides of the team and even customer success. And they should have very similar, if not identical definitions. And I think that's why there's that disconnect in pipeline numbers and revenue numbers and closed deals and things like that. It's so that we know.

KK Anderson (07:22.906)

out.

Kristina Jaramillo (07:46.39)

It's not a matter of like aligning all these teams internally, the go-to marketing. It's really about orchestrating and moving together as one. So whatever marketing does influences sales and then sales influences customer success. And it goes all the way again, when you do up in a circle, because customer marketing would get involved if that's something that your organization has. it's, it's everyone agreeing on it. And again, that whole revisiting it, not just letting it kind of be a stagnant thing.

KK Anderson (08:12.411)

So how do you determine what those strategic priorities are that your target market might have in common, know, over and above just typical thermographics?

Kristina Jaramillo (08:25.154)

Yeah, so what we typically do is we'll go to the customers that are the best customers. So the ones that are getting the most value, the ones that are using the platform or solution the most, and the ones that have great stories and examples to sell, and then kind of go by that. What do they look like before they came to us? Would they look like six months into implementation, 12 months, 18, whatever, and then try to go backwards. the approach that I'm talking about is a very narrow approach. So it's not.

necessarily scalable right away. It's what we've learned from this type of approach to scale our campaigns, scale our outreach, scale our nurture sequences. So we want to make sure that if we're selling six figure deals, that's our high end maybe. We want to look at what is that account that has closed at that and has all these characteristics that I just spoke about. And how can we kind of

target organizations that may be similar, but also we tell their relevant story. So we're not just telling the industry or persona story, we tell that account story. And then we can kind of scale back or scale that kind of approach and do it for like the one to few and one to many type of ABM approaches there are.

KK Anderson (09:37.659)

And so Define for me, I heard you say we tell the account story. So just for the person that's listening for our audience, just give a quick background on this whole concept of tier one, tier two, tier three, or one to many, one to few, one to one.

Kristina Jaramillo (09:54.014)

Okay. So to, yeah, yeah. One to many is more like demand gen in general, what people know demand gen to be. So you're basically trying to fill the pipeline. One to few is maybe they've engaged and they progressed a little further in their journey. So they're a little more relevant as you get further and further down. like from the one to many to one to few to one to one, you're getting more and more relevant. And one to one is I've heard people describe it as it has to be like an earned approach because

It requires a lot of attention. It requires a lot of input and resources. So it's basically for a one-to-one, you're learning what that account is, what is important to them as an account and how that trickles down. So what is the C-suite or what is the board saying at that account that's going to trickle down into the department that you're selling to? Like, how's that going to affect operations, customers, P &L, growth, anything that you can kind of tie your solution to?

And this type of approach again is for those bigger level accounts that we know are more, we've identified as part of our RCP, but we also know that they are more aligned with us. They have a strategic priority we can speak to and play a role in and just getting more and more relevant to them. So if you're targeting a bank, for instance, cause I have an example about this that I might get to later.

You want to tell the bank story, not a financial services story that has X amount of revenue, X amount of employees and customers, and X amount of locations. You want to tell that particular named bank account story. What's going on there? What are their initiatives for the next 12 to 18 months? What are they investing in? So are they more likely to be going into that digital transformation? Have they already done it? Where are they as an account?

And again, this approach is very labor intensive, but it reaps the benefits if it's one of those bigger deals. So this might not be, this approach I'm saying is not for every organization, but there are aspects of it that you can use it if you're selling a $25,000 solution or a hundred or multimillion dollar solution, hundred thousand.

KK Anderson (12:00.571)

Okay, so question. So when we think about enterprise accounts, we've got a lot of personas, a lot of different stakeholders that cross-functionally we may need to be selling to. So if you're doing that one-to-one approach, let's take your bank, for example, is there a number of stakeholders that you would market to? How do you adapt messaging and content based on your outreach strategy?

Kristina Jaramillo (12:31.278)

Well, when you redefine your ICP, so like if you're moving from a selling to mid market to enterprise, chances are your personas either change and if they don't change, it definitely expand. So I like to have at least three to five people engage and personas are going to change from even organization because we all know that everyone has different titles or different roles they play in every organization. So I would like to have a couple of people engage from influencer to if we can identify a decision maker or even a blocker or a challenger we can identify.

KK Anderson (12:48.741)

Yeah.

Kristina Jaramillo (13:01.08)

But we need to figure out what they typically look like and then the content that would be relevant to them. So if you're selling a solution, like a sales and marketing tech into an enterprise selling team, the AE is not going to have the same priorities as the CRO. So we want to make sure we're speaking to all those decision makers and all those influencers and speaking what's important to them, but what's important to them as a team. like the CRO is obviously going to care about things that are more tied to.

the business as a whole, team as a whole, whereas the AE might not, or even a director of sales might not. So we got to make sure that we're talking to their particular, like what's going to make them successful and how is your solution going to help them be better at their job? And also how is your solution better than competitors you've identified? Like where are the gaps and impacts in those competitors and where do you fit in better? Or how do you see those competitor gaps are going to impact?

the team and also, you know, in various ways, not just very in a revenue based way. And we need to make sure that we're speaking to that so that the team can make a decision and not get stuck in that indecision kind of like, it's a pain, but it's not a big enough pain for me. That means you haven't made that relevant connection. they could acknowledge it, but don't move forward.

KK Anderson (14:26.139)

Okay. And so that messaging, especially in that one-to-one approach, has got to be customized by person, super labor intensive. So what about in a one-to-few approach or a one-to-many approach? Because I would imagine that your campaigns kind of encompass all three levels. Is that right? So how do you, do you have to do hyper segmentation or something of your ICP?

Kristina Jaramillo (14:49.911)

Yeah, I mean,

Kristina Jaramillo (14:55.06)

Yes. And you also have to see if like an account, if it becomes more engaged, once they've entered the pipeline through maybe a one through too many campaign, if they become more engaged and you know that they have the potential to be a bigger value deal and there's more than maybe one person engaged and they've got attended webinars, they've downloaded assets, they maybe even replied to something and they have that potential to be a lucrative deal. That's how you can get them up to that one-to-one and whatever you're

like the content you're creating, the strategy and messaging you're creating for that particular one-to-one can be used to reengage similar accounts again in the one-to-many and one-to-few programs. So it's not a matter of all of the stuff that I'm talking about or all the strategy I'm talking about is just like for that one account. It can be used to kind of start that process all over again. And then once an account becomes like it hits a threshold of engagement and relevance and all it fits all these criteria's.

KK Anderson (15:51.483)

Mm-hmm.

Kristina Jaramillo (15:53.89)

then you can be know that's when it's time to really dive in. And it has to, there has to be so many signals from not just intense signals when I say signals before you develop that, because again, it's labor intensive and you don't want to waste time on something you know is or you can tell that's not going to move forward.

KK Anderson (15:57.691)

to really dive in.

KK Anderson (16:15.141)

So just curious, would you, let's say the signals are hitting and you decide to pull them out of a one to few campaign and upgrade them to a one to one, are you gonna engage in AE at that point or are you still with the BDR?

Kristina Jaramillo (16:30.798)

it depends on how much the BDRA might've already engaged with them. If they've already engaged, then we'd continue with them, but most likely because they're the bigger deals. They usually go to higher level salespeople and more experienced or they might, might be a team kind of thing because it, depending on how many insights there are from, who's engaged with them in their journey.

KK Anderson (16:43.237)

Mm-hmm.

KK Anderson (16:53.211)

Okay, let's move on to the next topic, which is fixing flawed ABM programs. This is one of my favorite conversations because it just seems like every single day, know, do you remember the book, Who Moved My Cheese? I'm dating myself right now, but.

Kristina Jaramillo (17:04.867)

Me too.

Kristina Jaramillo (17:10.77)

Yes. I remember seeing that title. No, you're not because I remember actually, well, I remember seeing it and my dad brought it home when I was like in college and was like, this is a weird title for a business book. And then he explained it to me. was like,

KK Anderson (17:23.267)

It's so good and I feel like our cheese is moving every day in sales and marketing, go to market strategy world. So, you you've worked with companies who've invested in all kinds of platforms like a sixth sense or demand base and different intent platforms and they're not seeing ROI. Like what's usually missing?

Kristina Jaramillo (17:48.024)

So it's interesting, I've talked to dozens of companies that are using these type of platforms or have used them in the past. And there's a handful that are always the same players that are coming in. One is it that they've relied on the ICP proxies within the platform, which again is not the ICP, it's at total relevant market. So it's too broad, it's not focused enough. Another one that's really...

a key player in having this not be as successful is there's a lack of change management. So if you have the wrong email, social live, even digital interactions and deliver those wrong account experiences, you're not going to convert it in market opportunity to revenue no matter how much intent the account shows. But a lot of people do that. And I've seen that there's churn rate issues or churn issues at these companies because they're not giving

A lot of the teams at these organizations aren't giving their customers the advice to be ready before they purchase this solution. And these are hefty investments. They're not cheap. And then these accounts are not converting. They're letting the tech drive the strategy versus having the tech support the strategy. So that is a big problem. And they just didn't do that readiness before they even adopted the platform to see if they were even in the right frame of mind to identify

you know, where the reds were in the business. Are they having a churn rate? Are they having a pipeline issue? Are they having an issue with accounts going dark or whatever disengaging? Another issue that I see with these platforms is that people are getting limited account insights. So the platform can identify the accounts, you know, that you might want to engage in. There's no guidance to what the intent was, why it was there in the first place.

what was the reason for it. So they don't understand necessarily the context behind the intent and why, you know, what's going on. There's no real direction to engage those accounts. Instead of telling an account story, we're going back to those persona and industry stories, just like your competitors. So we're all reacting the same way to the intent. So then if an account becomes unresponsive or goes dark, we kind of figure we're left wondering why and it's because we didn't

Kristina Jaramillo (20:12.056)

do the due diligence. Obviously you can't do that with every account, but the biggest, another big issue that I see is that a lot of teams aren't providing the account-based enablement to bridge the intent that's coming in to have, so no sales knows what to do with it. I've seen a lot of marketers telling me that, you know, we have six cents, we love it, but marketing or sales hates it. And it's because sales teams aren't equipped with the insights or the enablement to continue that conversation that marketing has started or engaged.

So they're being just again, going back to that handoff and there's no tools or messaging or stories so that sales can become multi-threaded. They don't have specific business cases to talk about. They don't have the tools to create that consensus and overcome that indecisiveness and move accounts to revenue. So there is that problem where one team might really like it and then the other team doesn't. It's because they're not equipping the team to maximize the platform and the results from it.

KK Anderson (21:11.003)

And then I imagine what happens is the unequipped seller probably then gets on the phone and just starts feature jumping. Let me demo, let me talk about our product, here's what we do, here's the problems we solve. And they may get some nodding heads and some, that's cool, but they're definitely not building the urgency.

Kristina Jaramillo (21:25.742)

Yeah.

Kristina Jaramillo (21:32.236)

Yeah. And so all that hard work that marketing did sales kind of backpedaled for them, but not because they want, you know, they wanted to, it's because they didn't have the resources and they didn't know what to do next. So they had an account that maybe was a little warmer and that they had been equipped with this insights or this knowledge up. They would have been able to address the conversation completely differently.

KK Anderson (21:55.205)

So do you have a preference for what type of platform or program that you recommend for these kinds of things? is that intent signal, mean, is that cheese moving as well, should I say? Like is that still as effective as it used to be?

Kristina Jaramillo (22:17.868)

don't think so only because so many people have it now. Before when it was like new and you were the only one or a handful of people that had it, it was one thing. But I know more platforms are telling you who the actual person is with the intent, but just telling me that a company, like if you give me that there's intent at Microsoft, doesn't mean what am I, how am I going to handle that one? There are some that are getting down to the person itself, which is very scary to me, but it's

KK Anderson (22:35.003)

Yeah, that's impossible.

Kristina Jaramillo (22:46.442)

It's more to me that it's become targeted to man gen. So you're doing demand gen, but you're doing it at a middle, more relevant, a little more targeted, but it's still a narrower spray and pray. It's useful. It's just not being used. And I don't think that a lot of companies can justify the ROI from it when it comes in terms of revenue as opposed to like, unless they're targeting or if they're

KK Anderson (22:59.675)

Mm-hmm.

Kristina Jaramillo (23:14.648)

keeping track of MQLs and MQAs and that's how they're justifying the spend. But if they actually turned and said, this particular tool in Sixth Sense or demand base led to X amount of revenue, I think it's very hard to justify the expense. We saw people that tech last or maybe like your three quarters away there and then you adopt a smaller part of the tech and then you grow from there. But if you do it first, you're going to have that tech for like six months before you've actually built what's go into it.

KK Anderson (23:28.431)

Wow, yep.

KK Anderson (23:44.365)

Or before you even know, like if you start using it and it's not working and you you've got the common pitfalls like you were just describing, you may not even know. So I've heard you say that ABM should influence revenue and not just generate MQLs. And you've talked a little bit about this already, but what are those like right metrics? Like what should...

Kristina Jaramillo (23:44.749)

So why do.

Kristina Jaramillo (23:53.142)

It's not the tool. Yeah, it's not the tool. It's the way it's being used.

KK Anderson (24:12.749)

marketers be looking at not just for ABM success, in general.

Kristina Jaramillo (24:17.506)

Yeah, so NRR is your ultimate metric. We want to look across that buyer's journey and customer lifecycle and impact stage progression, win rates, deal sizes, ARR, GRR, again, ultimately that NRR. So we are marketers in our organization, in our firm, but we really are focused on revenue as well. So we're assessing that go-to market. We want to look for what's happening. Where are we losing? Why are we losing?

We want to see if we're getting that VP and C suite engagement, because if not, then we need to build metrics around that. why not? Are we getting engagement across the organization or is it just the one department? And put metrics around that. It might not be relevant to your whatever you're selling, but a lot of times it is. are we looking at the lagging revenue indicators like stage progression, win rates, deal sizes?

and AR, GR, and NR and putting measurements around those to see where that business problem lies. So when we engage as a forum with people, we want to look at the biggest red in the business and address that first and develop the strategy from there and then move on to develop or to develop strategies for other areas that are revenue leaks.

KK Anderson (25:31.579)

So, kind of spilling into the topic of what's not working anymore in B2B marketing, I'm curious, how have your different channels shifted? Are you less on email, more on other channels? What are those kind of, how are you building up your intent signals?

Kristina Jaramillo (25:57.945)

From our firm, I'd say we're more on LinkedIn than we are on email. I'm seeing a lot for our customers as well because you can engage with your buyers in a different way. You can see what's important to them. What are they talking about? Why are they talking about these things? What is, and I'm not saying like personal, like they went to Penn State. I'm talking like, what are they doing in their role and how is it?

KK Anderson (26:01.859)

Okay, tell me about that.

KK Anderson (26:23.269)

Yeah.

Kristina Jaramillo (26:24.736)

How is the market impacted? How are the tools they might using be impacted? What they're doing and how they're achieving them. So you can do a lot of homework before reaching out to someone and knowing a little bit more about them before you send them that LinkedIn message or an email message, or you decide to call them however you're outreaching to them. And I think the same thing is happening for our clients is that they're using and market in general, that they're using LinkedIn, they're using these other tools and other platforms to see what's going on with that individual first.

So they can get relevant beyond you live in Phoenix or you went to XYZ University or you're working in this industry. I wanna get more insights the better and LinkedIn is one of those platforms that is like a plethora of information. And you could even see what the person might be writing on about or commenting on or things like that. So you get an insight into how they work and how their team might work.

KK Anderson (27:18.843)

How do you do that at scale?

Kristina Jaramillo (27:22.06)

That at scale can be hard, but BDRs can definitely like say if BDRs are working on your one to many or one to few, they can use Navigator. They can use regular LinkedIn subscriptions and do a little bit of homework before. And again, digging deeper, like they have to be told and taught to dig deeper than those generic similarities. What might be bad? What's influencing them on their day to day and how can what you're selling or

KK Anderson (27:43.226)

Right.

Kristina Jaramillo (27:50.094)

How can your solutions or your platform, how can it help them be more successful? And you got to position it that way versus, you know, I know that you're in this industry and we've seen a lot of people in this industry have this problem.

KK Anderson (28:02.607)

Right, it's almost the exact same thing you were just saying with the one-to-one in an enterprise account. Like it's not good enough to have just that market story. You have to have the account story.

Kristina Jaramillo (28:14.7)

the account story. Yeah, I mean, when's the last time anyone closed a six or seven figure deal with just sending generic thought leadership or industry leadership? I mean, it might, but yeah.

KK Anderson (28:22.147)

Yeah, it's probably been a long time. So it's a LinkedIn connection and then a LinkedIn message is another way that you're doing it. What else? Are there any other like intent channels that you've been seeing that work in getting engagement with enterprise just primarily? I mean, are you using email still?

Kristina Jaramillo (28:44.302)

Kristina Jaramillo (28:49.272)

I am, but it's very like compared to what it was. I do LinkedIn first. If I get engagement versus like say I reach out to someone that I know would be a great fit because we have a business case, we have a case study, we know what's going on strategically. We did all our homework. They engage with me by connecting because I'm sending them a relevant message. And then I send them, I might send them up a couple of weeks later, another follow up message to.

KK Anderson (28:52.667)

Tell me about that.

Kristina Jaramillo (29:15.362)

read a certain article and they don't engage with that because the LinkedIn inbox can sometimes be a black hole. Things just get lost in there. Then I might try to find their actual email address and try to reach out to them that way. And then maybe send one or two followups to nurture them that way. email is always like my last resort only because it's not, I feel like it's intrusive, number one, like you're getting to the person's inbox that they basically live in.

and you haven't necessarily earned the right to get there. And I don't want them to think that I'm just another person selling something. Like I have to, if I'm outreach with them, I'm, there's a reason. So there's a reason is I have information to share that's relevant and I have content to share. I'm not just saying, let's jump on a call because I know that I get dozens of those a day and I ignore all of them. So it's definitely happening at the enterprise level. So I always say people, if you're going to...

reach out to someone, whether that's on LinkedIn, whether that's email, however you decide to engage with them, there has to be a reason. Like it's not just that you want to sell them. That's not the reason. It's because I know that XYZ is happening at your company and this article will explain how to address it or how to be proactive so it doesn't happen to you as well. So you're giving them value and it goes back to value selling. And that has to be something that marketers, like I think that's a lot of a big problem with this is that a lot of marketers are not.

educated in the ways of selling. And that's why there's such a disconnect because they just think of marketing in those very brand awareness type terms as opposed to, well, what's going to move that revenue needle forward? Like does a salesperson, would they care about the features and benefit article to share to their, their prospects? Most likely not. Cause it's not as successful for them. So I think when you're in the sales,

Like you put on a sales hat or you walk in their shoes or you listen to a sales call, you understand them so much better and you can write for them better. You can produce content and produce assets for them so much better when you know where they're coming from and you speak their language.

KK Anderson (31:20.987)

Yeah, I was just about to say you're speaking my love language.

Kristina Jaramillo (31:26.446)

You have to, if you want them to be successful and you want them to work with you in a consistent basis, you have to speak their love language, which is revenue. Like it's not.

KK Anderson (31:35.301)

Right, right, exactly. But as a sales leader and sales coach myself for decades now, I find myself saying probably on a daily basis, like it's serve over sell. And I don't care if you're selling a metal valve or you're selling a seven figure SaaS product, right? It does not matter.

If you want to differentiate in today's market, you must serve over sell. If you're not helping them solve a business problem, if you're not consulting with them on how to advance their career, what's in it for them, you're not going to get anywhere. Right? And so it is, how can you help them?

Kristina Jaramillo (32:26.882)

Yeah, how do you want to be perceived too? Do you want to be perceived as a partner or a vendor? And marketing has to think about that too. And I think that's the best.

KK Anderson (32:29.787)

That's right. You want to be a And it's almost like, how can you get them to say thank you? Like, wow, that was nice. Right? And so when you're coming into their inbox, you you want to do that. That makes it a lot more tricky. I'm curious to get your take on cold calling and having BDRs pick up the phone and call people. I, you know, obviously you want to do that with a serve.

Kristina Jaramillo (32:39.937)

Mm-hmm.

KK Anderson (32:58.051)

over sell mentality as well. But talk to me about, I know we're going a little bit off track here, but how you combine your call with your LinkedIn, with your email and your approach to really try to deliver some value.

Kristina Jaramillo (33:15.648)

Yeah, so I am the last person you want to talk to about cold calling. But if you were to have, like say you have a set number of accounts or whatever and you're trying to outreach to them, again, are you calling to hit your number of calls for that day or are you calling to actually engage with someone? So I am always quality over quantity. And again, if you're not teaching, even in that, even if you're doing a cold call, if you're not trying to teach them or say, you know, page three of this, you know, executive

brief that's 50 pages and really long is really where you should focus. You might not need to read the whole thing, but definitely page three you need to focus on because it's got X, Y, and Z in it is way more beneficial and interesting to me than saying, here's a 50 page report. Get to like, good luck. Add that to your list of reading for the day, evening. And it's, it's, it tells them that you read it too. And you know about it and you're more in a

KK Anderson (33:59.695)

Yeah!

Kristina Jaramillo (34:14.146)

well-read on their industry and what's going on with them. And then you even took the time to pinpoint something that they should care about and why. Totally different conversation than saying, you know, here my product and feature dump and this is why we're better than XYZ competitor.

KK Anderson (34:25.807)

Right. You have to earn the right to be able to talk about yourself. Right? Yeah.

Kristina Jaramillo (34:31.326)

Absolutely. Yep. A lot of sellers know this, but marketing needs to get on board too.

KK Anderson (34:36.091)

That's true. So, okay, so if you're, you know, for the CMOs out there in the audience that are listening right now and, you know, kind of steering back to the ABM concept of this one-to-one, then one-to-few and one-to-many, you know, marketing, like what should they be thinking about when starting and executing an ABM program to go up market to enterprises?

Kristina Jaramillo (35:07.64)

So right now I would really focus on building the right foundation to change those interactions that the teams are delivering and how the experiences are being delivered, how the account experience is being delivered versus what I see a lot of people doing and then have their ABM program fail and then wonder why. Is there retrofitting ABM on top of what they're already doing and just using it to source the pipeline?

And ABM can be used to sort the pipeline, but it's not as effective as it is to actually driving change with the accounts, moving those accounts forward and driving revenue. So I have an example of this. I recently spoke to head of marketing and an AP and automation FBA FPNA tech. So they wanted to see how they could fix their ABM program. They had started it eight months ago, so it was relatively new.

What they really needed to do is recalibrate what they were doing. Their frameworks needed to change, their processes, their metrics. They had done this retrofitting of what they were already doing and they were not seeing the ABM returns and the time and investment. So we noticed it was that they were putting ABM just on new logo acquisition, which you can, but it's much more difficult to do versus reviewing that go-to market like we've been talking about.

and they were also defining their ICP with generic things. So a generic trait. So for them, it was like how many transactions they had, you know, what did their, you know, platform look like? What did their ERP environment look like? They were not segmenting their existing customers to see where they had the greatest long-term revenue with those kinds of customers. And then looking at them.

to see how they could get similar characteristics beyond those demographics and technographics so they could better define their ICP. They hadn't redefined it or readdressed their ICP. So these are things that people really need to do before they develop an ABM program in order to make sure that it's successful. Otherwise, you're looking at maybe six months, maybe less before you're like, it's not working. We're gonna leave it.

KK Anderson (37:23.137)

You said something that I want to, I want you to double click on for me, Christina. You said maybe they're using it on net new acquisition versus their install base is what I'm, what I'm assuming. Tell me more about.

Kristina Jaramillo (37:37.612)

So for us, what we've seen the most success and what I've seen other people even say this is that ABM really has success, greater success on retention expansion than it does on net new. Because to me, net new, a lot of it has to do with demand. So if we are, we know there's a dozen accounts that are up for renewal and we need to know this ahead of time, not 30 days before renewal.

KK Anderson (38:04.987)

You

Kristina Jaramillo (38:07.118)

because you can't throw together a strategy that quick. They're renewing and they have a potential to expand because they've been using us on a weekly or monthly basis versus an account that's only been using us on a quarterly or annual basis. Then we need to know what we need to do to address the stay, why stay, why now conversation and why expand. Like this is what you look like when you came to us, this is what's happened since you've worked with us and this is where we see opportunities in the next...

know, six months to a year, however your contracts are situated, areas for growth. So you're again, going back to that, seeing as being seen as a partner to grow their business, as opposed to just a vendor of a solution. And you can expand that account, maybe either they can have different features or different solutions that you offer, they can add on to what they're already buying, or maybe they have business units that you need to break into and they can help you kind of break those walls down. So it's all a matter of

trying to get these accounts to grow and stay with you, then land and expand. It's doable on land, excuse me, land that new. It's just a longer road. And I think people don't think of it and they think, ABM will just fix all my problems and we'll land that new within 30 days.

KK Anderson (39:07.739)

Come on.

KK Anderson (39:21.881)

Yeah, and why is it that it takes longer with the NetNew?

Kristina Jaramillo (39:27.626)

It's similar to the fact that you need to do all your homework on an account that's net new versus if they're a customer, you have most of that done for you already. Usually what's harder enterprise-wise, same thing with ABM like normal sellers have.

KK Anderson (39:31.493)

Yeah.

Yep, got it, okay.

KK Anderson (39:43.323)

Okay, well that is some great advice for our CMOs listening. Let's shift over to, I'm having so much fun talking, I'm losing track of time. Let's shift over to, and we've talked a little bit about this, but that marketing to sales handshake, right? Really closing the gap between the two. What does that look like in practice?

Some may say you get an MQL, you hand it over to sales and then they're off. You've talked a little bit about this, but how do we really make that overlap?

Kristina Jaramillo (40:24.558)

So basically means you're not just working accounts to pipeline on the marketing side and giving sales that intent, the engagement, and then sitting back and waiting for them to tell you what they think they might need or what they need based on that selling cycle. You're proactively working to influence the selling conversation on the marketing side. As a marketer, I'm providing account insights that sales need to have that right engagement. We're providing them with content to support them, to help them reframe conversations content to...

support them once, you know, if they've celebrated through the selling cycle and now it's just internal conversations, what kind of content am I, supporting them with so that they can be, have these conversations internally and, and go in our favor. Are we providing with stories on the reframes they need? Want to make sure that they're also providing account based value props, conversational support.

We're helping sales enable buyers to make that trade off between what they're doing now and working with you, justify the business case and have that confidence to make a decision that's going to drive change. Cause obviously change is very scary. It can be expensive. It can be timely. We're helping sales overcome those issues with these prospects and bring those different buyers together. And we're helping sales address those struggles that they're dealing with within particular.

So we've already either they've seen them before so we know how to enable them or there's something new and we need to learn how to enable them. So we're thinking of working alongside sales and account teams until it's revenue or there's greater revenue growth. It's all about making marketing accountable for revenue just like making sales teams accountable. It's obviously not going to be the same numbers and the same metrics and things like that, but all teams should really be accountable because an account based approach

really should be joint sales and marketing and a CS win. I know it's account-based marketing, but I like to say account-based go-to market instead because it makes everybody accountable as opposed to just one team. it's, especially in this day and age, it's very hard for just sales to do everything alone. It's virtually impossible.

KK Anderson (42:29.167)

No.

KK Anderson (42:39.887)

Right, that's really interesting. I like that account-based go-to-market. Yeah. So how often are you recommending that sellers should be meeting with their marketing team?

Kristina Jaramillo (42:58.522)

so depending on how you're structured, say someone who's the, the ideal idea would be that there's a marketer aligned with segments of the sales team. And I would say like ideally weekly, but if not at least monthly, so we can see like, where are these deals stuck? Are they progressing? Do you need additional support? Do we need to have, do we need to create a webinar content or a case study based on what you're having a problem you're having? Because we've seen it two, three, four times already.

So obviously this is something we need to address as a company or as a team. So you can check in because if you're just kicking them over the fence and just hoping something happens and then waiting to the end of the quarter to see what's going on, it's too late. It's really too late.

KK Anderson (43:39.183)

Right. That is such a great point. That is such a great point. Okay. So let's see. When you think about, you know, just last week, I don't know when it dropped on our podcast schedule, but I think it was last week, we had an interview with Cathy Minter, who she used to be a co-host of Selling the Cloud, and she was our guest last week. And she talked a lot about a unified CRO model where

marketing, sales, customer success, a lot of what you just said. Like it's interesting how all of these conversations are all happening at the same time. Like it's so important that everyone is unified under one kind of leadership. And so, you know, I know this is kind of putting you on the spot, but like what's your perspective on that? So if you have one, let's say your chief revenue officer and you've got marketing, you've got everyone in the revenue organization is kind of reporting up. Like what's your perspective on

or do you feel like they should all be separate?

Kristina Jaramillo (44:40.782)

So if you have a CRO and everyone's reporting the CRO and not necessarily a CMO, that automatically means that you should be focused on revenue. But ideally, I like it so that the BDRs are under marketing. Because then it's almost like marketing gets to train them on what they need to ask for to support. And then we can know how the higher level business development or sales team needs, what they're going to need.

KK Anderson (44:55.855)

Okay.

Kristina Jaramillo (45:09.274)

In a perfect world to me, there would be a CRO and a CMO and they're in lockstep about how they're going to hit the revenue goals together. And they're constantly meeting because then that trickles down to their respective teams of how we're going to work together. Because if you see them align, then it's much easier for the teams to come together. But if they're not working together to hit these revenue goals, that's where that misalignment happens. That's where I'm going to give you MQLs and then hope for the best at the end of the quarter, of the year.

KK Anderson (45:21.871)

Mm-hmm.

KK Anderson (45:35.794)

huh.

Kristina Jaramillo (45:37.454)

So I think it's all a matter of that changement internally, change management.

KK Anderson (45:40.997)

So any kind of stories or experiences that you've had where either there's been a really strong handshake or where there's been a gap and that alignment story is so interesting to me because I feel like that is an obvious gap for so many people that are listening. For one, just to say like a CMO typically has real data. They've got numbers, they've got all kinds of data that they're looking at.

And a CRO, unless they're using like a platform like Collective Eye or something, they don't. have, well, don't, know, our seller says this deal is going to get pushed because of this or that, or, know, it's all, you know, it's all speculation and opinion. so, you know, that causes a lot of consternation a lot of times between CMOs and CROs and to their CEO, right? So just anything comes to mind as far as, you know,

Kristina Jaramillo (46:22.286)

So big, right.

KK Anderson (46:40.805)

clients that have done this really well or...

Kristina Jaramillo (46:45.962)

Yeah, it's, it's when there is like, if we go into an organization and the sales and marketing leaders are not on the same page or we don't have access to one or another, we already know that our success rate is going down. we've worked with organizations where they will keep us completely siloed from sales. So we've developed great content. They've been engaged, they've engaged with it in campaigns, but we don't know what's happening after that because they are so siloed internally that

we cannot get past them. So those clients don't wind up being a great fit for us because we want to make sure that we're impacting revenue and there's no way for us to know we are. Like they've engaged with content from us, but we don't know what happens after that. So it's very hard when there's not both. ideally for us, we come in where there's alignment or we come in and we work directly with the selling team and we're working with the VP, senior VP of sales or the CRO because we're creating that

strategy and content and messaging for the selling conversations that he knows his team's already having, but they just can't get that level of attention from marketing because they were either not on the same page when it comes to that, because they're more brand awareness and they're more metrics on campaigns. Don't have the manpower because it is like, as we've been talking about, what we do is very time consuming. But if you can, if this, let's say

program I'm running, takes me three months and I close a six figure deal, then it's worth it. Because then we can try to replicate that or we can try to influence the smaller deals. And then we can give a lot of this information to marketing so that they can optimize the programs they're running. So it's, it's very hard if there isn't that change management. And I've heard, I've talked to a lot of people that are in marketing that they want to do all these great things, but there is no senior leadership alignment, but they want the results. The senior leadership wants the result, but there isn't that alignment.

And they say they're aligned, they're not really, in theory they are, but not, they're not orchestrating and moving as one team. So like an ideal role, the CRO and a CMO would be best friends.

KK Anderson (48:53.467)

Yep, 100%. Okay, so let's move on to, excuse me, rapid fire questions. This is my favorite part of every episode. And Christina, what we like to do is just ask some quick questions and you can give us your knee jerk reaction. Okay, what was, well, let me see, every good marketer has to have sold something at some point. What was the first product or service you ever sold?

Kristina Jaramillo (49:11.864)

Got it.

Kristina Jaramillo (49:23.086)

So if we wanna go back to like the original original, I would say Girl Scout Cookies.

KK Anderson (49:26.427)

There you go. Door to door.

Kristina Jaramillo (49:28.694)

Yeah, but then after, yeah, well then after that, yeah, well actually I even my dad, I even got my dad in on it. He would bring in, this was back when they actually had paper forms and you put your name and like checked how many you wanted, like a thinment. He would bring the form in to work and we lived in New Jersey, but he worked in New York. So he would take the train, bring the form in, he'd come back and he'd sell like hundred cookies or boxes. And then he'd have to come in for like three or four days, a couple of weeks later with duffel bags.

Anything for like a reward.

KK Anderson (49:58.659)

So you are delegating very early. You were an entrepreneur even then.

Kristina Jaramillo (50:04.558)

It helps that my dad and I are very close.

KK Anderson (50:06.797)

I love that. Okay, who's your favorite CMO or go-to-market strategist to follow?

Kristina Jaramillo (50:14.742)

Yeah, so he was a CMO, believe he was. Yeah, he was CMO, but he's a go-to market strategist now Sangram Vahri at go-to market partners. He's one of my favorite because he tells it like it is and it's no sugar coating it. And he's telling you, you don't have a sales problem, you don't have a marketing problem, you don't have a customer success problem, you have a go-to market problem. And a lot of the content that he and his team shares is very relevant. So if you're not following him, I suggest it.

KK Anderson (50:38.651)

That's really great. then, I should say, Christina, you and your partner produce some amazing content as well.

Kristina Jaramillo (50:45.826)

thank you. We're very busy.

KK Anderson (50:46.795)

Yes, some amazing content. So definitely go follow their newsletter and then you also have a podcast.

Kristina Jaramillo (50:55.478)

I do, we do have a podcast. You're going to be on it, I believe next week.

KK Anderson (50:58.048)

Yes. And tell us what's the, tell us about the podcast and where they can find it.

Kristina Jaramillo (51:03.34)

Yeah, it's on every platform wherever you listen to. I just happen to be a Spotify person, but it's called the ABM Done Right. And we talk to people who have both sides of the fence. So sales and marketing leaders that are typically in the tech and SaaS industry, and they're selling complex solutions. So they know all the things that we've been talking about. And they really just want to optimize their programs. And they're telling you lessons learned, what works, what's not working.

why they recommend certain platforms and certain strategies and people will tell you like the honest answer of, know, we adopted ABM before we ready or we, you know, adopted ABM and then ran it for three months and didn't give it a chance. And so that we have to start again. So it's, it's, I learned a lot and it's a, I nerd out a lot with people that I don't necessarily get to talk to otherwise. So it's, it's something fun.

KK Anderson (51:51.555)

Yeah. Okay, so what is a leadership or go to market practice that you think every sales or marketing leadership adopt?

Kristina Jaramillo (52:01.986)

So I think a lot of people need to focus on their why. Why are we running this campaign? Why are we reaching out to this company? And if you can't figure out the why, then maybe you need to go back to the drawing board. Or why am I picking up this phone or sending this email? Because I think a lot of people are just focused on the tasks they need to do, that they get stuck so much in the weeds of the tasks that they forget the strategic part and the strategic reason we do all these things.

KK Anderson (52:30.235)

Start with Y. Start with Y. Okay, advice you'd give your 21 year old self.

Kristina Jaramillo (52:37.07)

Um, let's see advice to give my 21 year old self would definitely be to travel more. I definitely traveled more in my twenties, but I should have traveled even more internationally. And I would say if you have a passion that you want to follow, that's the time to do it. I mean, you can do it in your forties and fifties and sixties and beyond. It's just harder. So if I had, if you had something that we're passionate about at that time, other than traveling, that was what I was passionate about. It probably would have gone down a different road.

KK Anderson (52:55.483)

So much fun.

KK Anderson (53:02.987)

Yeah, really, really great advice. I have a 20-something year old niece, two of them nieces, they're both in Italy right now and I'm thinking to myself, God, I haven't been there since I was in my 20s.

Kristina Jaramillo (53:15.382)

same feeling I love it on.

KK Anderson (53:17.499)

Okay, last one. What's your favorite business book? What would you recommend to your readers for, to our audience for a good read?

Kristina Jaramillo (53:26.38)

So I know you said business book, I'm a really big, I'm a nerd because we always focus on the go-to market. I'm reading a lot of only sales marketing based or go to meet, go to market books. So my top two, would say would be the challenger sale, which people I should, if you haven't heard about it, Google and look it up. And my favorite, there's a couple of different challenger ones, but the challenger customer, cause you kind of get inside the head of what the customer is thinking and then it can makes you a better marketer.

And it sounds like it would be more of a seller's book, but it totally is for both sides of the team.

KK Anderson (54:01.614)

the challenger customer.

Kristina Jaramillo (54:03.936)

and the jilt effect that's written by some of the authors from... Yeah, it's a good one.

KK Anderson (54:05.657)

yes, I've read that one. Yeah, that is an awesome book. Okay, awesome. Well, Christina, thank you so much for joining us today. And we will include all of your recommendations in the show notes and then also your LinkedIn profile and a link to your podcast as well. Yeah, it was a lot of fun. Okay, talk soon.

Kristina Jaramillo (54:21.666)

Thank you so much. really appreciate it.

Kristina Jaramillo (54:31.79)

All right.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this Part 2 episode, co-host Mark Petruzzi continues the conversation with Jack Zimnavoda, Head of Customer Success at Insightful. This time, they explore how Jack’s team is scaling Customer Success by embedding AI, aligning post-sale marketing, and applying smart segmentation strategies.

Jack shares how predictive tools, data-informed health scores, and hybrid touch models enable CS teams to identify churn risks, streamline workflows, and drive expansion; all while maintaining a personal touch.

What You’ll Learn

• Predictive CS in Action: Jack explains how his team uses AI within their CS platform to surface risk, recommend proactive next steps, and highlight expansion-ready accounts.
• Marketing + CS = Growth: How Insightful brings CS and marketing together to educate customers, promote feature adoption, and scale communication—without losing personalization.
• Segmentation for Scale: Why Insightful uses a hybrid touch model to support over 5,000 customers across different industries and sizes—without compromising value delivery.
• Retention Forecasting: Discover how qualitative inputs, usage data, and AI models combine to anticipate churn and improve long-term customer outcomes.

Key Topics

• Building a predictive, AI-supported CS platform
• Aligning CS, product, and marketing post-sale
• Hybrid-touch models for scale
• Customer health scoring and churn prediction
• Operationalizing expansion strategy
• Creating scalable CS motions with a human touch

Guest Spotlight: Jack Zimnavoda

Jack is Head of Customer Success at Insightful, where he leads global efforts in retention, adoption, and expansion. With over 10 years of experience in B2B SaaS, Jack has developed practical, scalable strategies that connect Customer Success with revenue growth.

Resources & Mentions

• Book: The Seven Pillars of Customer Success by Wayne McCulloch
• Podcast Mention: This is Growth by Daphne Costa Lopes
• Tool: Vitally – CS platform used by Insightful

🎧 Listen now and follow Selling the Cloud for more expert insights on scaling GTM teams. Subscribe wherever you get your podcasts.

Mark Petruzzi (00:04)

Welcome to today's episode of Selling the Cloud podcast. We're thrilled to welcome Jack Zimnavoda, Head of Customer Success at Insightful. Jack is a seasoned CS leader with a deep passion for helping companies retain and grow their customer base through intentional customer success strategies. He has built teams that drive renewal, expansion, and adoption at scale, and he's helped shape

how modern B2B SaaS companies think about customer-led growth. Today, Jack will explain how customer success can become a core growth engine through better cross-selling, upselling, and alignment with the rest of the go-to-market organization. Today, we'll explore four areas. One, we're thinking customer success as a revenue driver. Two, building a customer-centric expansion motion.

three, partnering with sales, product, and marketing for go-to-market impact, and four, metrics and models that power scalable CS growth. All right, well, again, Jack, welcome. We're very excited about having you here, and we can kind of kick off into topic one. But again, first, welcome.

Jack Zimnavoda (01:20)

Thanks so much. Really, really excited to be a part of this podcast and ready to dive into it.

Mark Petruzzi (01:26)

Perfect, all right. Topic one, rethinking customer success as a revenue driver. That is something that I have been in the middle of for many years. And it's funny, you get all different views on this straight up to the CEO and the board. You have a typical customer success mindset of, I don't wanna be selling, I'm not sales. But at the same time, that's evolved as we all know how important

the upselling and cross-selling process is and how that can't be done successfully without the support of the CS team. So Jack, know, CS has been viewed as a post-sales support function in the past. What needs to change in mindset and structure for it truly to become a revenue driver?

Jack Zimnavoda (02:20)

Yeah, so it's a totally fair ⁓ mindset that go-to-market leaders have there of customer success being an offshoot of support, particularly for leaders that have been around in go-to-market ⁓ leadership for 20 plus years, because truth be told, customer success was an offshoot of support. ⁓ I started in this career back when it was account management, and then it's gone into its own... ⁓

know, evolution since then. But also, I think it's fair to say that that gap in the understanding of customer success being a support function versus what it's really intended to be these days is narrowing, right? I think these days, customer success, especially at SaaS firms, is kind of a core piece of the go-to-market team. And I think most people don't view it the way that they might have 15, 20 years ago.

⁓ In those instances where it is still viewed as a higher level of support, think really what needs to happen is a change in mindset first. And that doesn't happen by somebody saying, this works well at other companies, we should do it. ⁓ I think it kind of happens by experimentation, right? Letting the customer success team ⁓ go to their customers and offering ⁓ new things to them, whether it's new use cases or

expansion to different teams or through different product offerings. And the proof is in the pudding in those cases. So I think with that experimentation, when you show small wins like that, it automatically changes the mindset. ⁓ And once that happens, you could think about changing the structure of teams.

Yeah.

Yeah. These are really, you know, very real problems that customers have, or sorry, companies have when they start introducing customer success as a revenue generator, right? The truth is there's no one way that this works well. I've seen it done in so many different ways. I've seen pods created where CSMs are coupled with salespeople. I've seen, you know, customer success managers own all revenue operations post the initial point of sales and own a quota.

And I've even seen, you know, and I don't recommend this, I've seen CSMs essentially treated as SDRs to go out and find opportunities and feed them back to the sales team to manage. You know, I'll just speak to the way that my team is set up because I think it works quite well in the way that we're working it today, which is that my team, ⁓ the way that that insightful works is that the sales team has a certain period of time whereby they're able to expand the accounts that they bring in.

⁓ But if that period passes, then the success team has the obligation really to nurture those accounts, find opportunities to take them from identification of the opportunity all the way through through close. And really we incentivize the team to do exactly that. So ultimately, I think any of those types of structures can work. It's just a matter of ensuring that incentives are aligned and that expectations between the teams are

very very clear.

Mark Petruzzi (06:51)

Great. So Jack, where do you see most companies going wrong when they're trying to turn customer success into a profit center instead of a cost center?

Jack Zimnavoda (07:02)

Yeah, great question. Two things every time. The first thing is that there's a lack of understanding sometimes when you want the customer success team to take on ⁓ the ownership of the revenue. ⁓ Lack of understanding of what the CSM team has on their plate already from a responsibility standpoint. And then blindly thinking that they could add opportunity, identification, and realization.

without negatively impacting those other areas that are already on their plates. So I think when you look at bringing this into a customer success team for the first time, it's really crucial that there's a plan in place to offload some of that non-value added work prior to making the shift so that hopefully the customer success team has a bandwidth to focus on this area plus the core competencies that they've always had.

I would say the other thing, and I mentioned this in the previous answer, which is not aligning incentives to the intended outcomes. So, you know, if you're starting this out and you've got your customer success managers judged on things like client sentiment or the number of quarterly business reviews they're doing or gross retention, there's really no incentive for the CSMs to grab onto this opportunity for them with everything they've got.

And just bringing this once again back to my team. I handle this by giving them incentives in two ways. The first is by giving them quarterly bonuses that's based on that retention, which of course factors in expansion dollars, but is really rooted in retention. But then on top of that, there is a small commission opportunity, but they're focused on non-organic expansions, meaning these opportunities have to be identified.

by the CSM, they really have to be the ones responsible for drumming up this business and owning it from identification through close to get that commission.

Honestly, I have not dealt with that struggle too much. And the reason is we set expectations extremely clearly upfront. We explain why the business is going in this direction, which is ultimately to grow revenue business-wide. And also, for me, it's a matter of showing them the previous data. Most of the time, salespeople can get territorial over their accounts, and that's understandable. But when you take a look at their commission payouts,

I'd say nine times out of ten, the vast majority of their commission is coming from new business anyway. It's just kind of a mindset that needs to shift of, I should just be focused on new business and that's the key area that the company needs me to focus on and that I'm getting paid for.

So I think it should work together pretty seamlessly, right? think sales and customer success need to be working hand in hand. And that is regardless of if customer success is owning the expansions or not. There needs to be a very solid understanding, foundational understanding of what the accounts need, what their use case is, what are their goals that they need to achieve to be able to say, yes, this expenditure was worth it.

⁓ As long as you have those kind of key points in play, then the rest I think falls into play pretty naturally. Again, making sure that you're not overloading any particular team with so much that they can't handle their responsibilities.

Mark Petruzzi (11:22)

Cool. I've got one more on this to double down a little bit. What are the early signs, Jack, that you see that gives you the indication that a CS team is being too reactive instead of being able to make that jump over to the strategic side?

Jack Zimnavoda (11:42)

Yeah, that's a great question. ⁓ For me, it's really simple. If we're finding examples of churn, customers leaving us, and they come as a surprise to the CSM, it is a clear cut sign to me that they're just too in the weeds of resolving issues that are brought to them and not taking the time to have proactive conversations with their customers about what their goals are, what kind of value they expect to see. ⁓ Any time that that

churn is brought up and we don't know what's going on there. I need to take a step back and I want my team to take a step back to really understand what happened there in terms of their involvement with that account because it shouldn't be a surprise.

Yeah, think there are a couple of things that are constant, whether it's a new logo or an expansion, right? Those things are, you know, solid understanding of what levers there are to pull for increases or expansions, right? Is this a play to sell professional services or is it add-ons that are available to them? Just understanding, you know, what's in their tool belt that they can rely on. And the other thing that I think is a constant between

whether it's an existing customer or a new customer, is a really solid understanding at the very minimum of the industries that you're serving and what challenges they're facing. Even better, obviously, if you have a solid understanding of the customers specifically and what their challenges are. But then there are things, I guess you call them ingredients, right, that are a bit more unique to existing customers.

The first is incredibly simple but incredibly powerful, think, and that is, are they a happy customer? You can have great products, ⁓ you can have a really solid process for onboarding those customers, but at the end of the day, if a customer is giving you feedback that, for whatever reason, they're unhappy, maybe they're not able to achieve their goals or they felt that the onboarding process didn't work for them,

The focus can't be on selling that customer more at that point. It needs to be on fixing that problem. So I think there are a ton of signs that you could get for existing customers that you can't necessarily tell with a new, a net new account in terms of whether or not they're set up for a good expansion conversation. And then the other thing, the other ingredient I would say that's really great to have. I don't think it's a must have, but it's...

certainly nice to have, is there's no shortage of tools that a customer success team can rely on to know whether their accounts are primed for expansion. I'm a big proponent of using predictive AI tools that help you analyze the conversations that are happening between the CSM and the account that are able to take a look at the data in your customer success platform or in your CRM.

and predict whether or not this account based on a lot of their traits or whatever are a good candidate for expansion. When you're a company like Insightful where you've got 5,000 customers plus, don't have time, or the CSMs don't have time to sort through all the data on their own. So having that kind of predictive insight is really valuable in using their time wisely and focusing on the accounts that are

you know, really ready for that expansion conversation.

I'm sure there's more, I'm ⁓ I'm blanking out the others.

Mark Petruzzi (16:19)

So Jack, tell us about how you work on training CSMs to have these types of commercial conversations without turning them into full-fledged sales reps.

Jack Zimnavoda (16:32)

Yeah, ⁓ I think part of it doesn't really go into training. It comes into hiring the right people. ⁓ And what I mean by that is, you know, when I'm hiring for CSM roles and I just actually had a couple of interviews this week for a new CSM role in New York, the two kind of mindsets that I'm looking for that I think are great for this position are curiosity and also creativity.

⁓ I think when customer success managers can go into conversations with the mindset of genuine curiosity about, you know, customers' businesses, you know, how they're making money, ⁓ what their challenges are, and also creative approach towards problem solving for those challenges, conversations that lead to upsells or cross-sells really just happen naturally. So I think that's the first piece of it, is hiring for the right...

sets of soft skills, if you will. ⁓ Having said that, there's also tactics that we could train on. ⁓ One of those tactics for my team is when we're running quarterly business reviews, before that takes place, I'm having my team do a lot of research on the accounts that we're working with outside of just the departments we're working with. We're trying to identify stakeholders that may not even know about Encypheal, could find value in it.

And then we're going back to our champions and we're saying, Hey, let's bring them into the quarterly business review so they could understand what we're doing with XYZ firm. and it's just a very natural conversation. So I think, you know, we have the benefit of being able to have these non-sales conversations, that very naturally go into a direction of expansion in one way or the other.

Yeah.

And also I double down on that. think that serving and selling are absolutely not mutually exclusive. I think in order to serve, sometimes you need to sell and that's not a conflict of interest in my mind.

Mm-hmm.

Exactly, right? That's ideally that's what they're doing. Yeah

Mark Petruzzi (19:33)

So when you look at this overall, Jack, so what kind of role does customer segmentation play in the whole entire expansion strategy, the entire growth go to market?

Jack Zimnavoda (19:47)

Yeah, it's for a company like ours, it's massively important. You know, we've got, again, 5,000 customers across, know, across the globe, truly serving dozens of different industries. You know, if I were a CS leader of a company that sold a $5 billion product and only had 30 customers, it's not as important, right? ⁓ Segmentation matters less in those instances. You just have to be insanely knowledgeable about each and every one of those.

businesses. ⁓ But in cases where you have a larger customer base, ⁓ yeah, absolutely imperative. We segment by customer size, their industry or vertical, what their potential use cases are. And these are really just goals when it comes to setting up expansion plays. The way that we handle, let's say, a massive organization that's only using us for one department is going to be

completely different than the way that we try to upsell a 300 person company that's already using it for all their employees. There's just different plays that are going to go into effect for each of those scenarios. But also the value propositions are going to be wildly different between these segments. There are some propositions that are going to be game changers for certain industries that are completely meaningless to others.

kind of summarize all that, the more that you can slice and dice your segments based on whatever you have, key traits, personas, use cases, know, whatever you have, ⁓ the better your opportunities are to create messaging that is, at least feels personalized to your customers and can be done in a scalable way.

So right now our customer base is segmented mostly on revenue size. And yeah, we do have our enterprise segment, which as you might expect, is essentially white glove service with ⁓ custom or bespoke onboarding, ⁓ regular engagement through the adoption and ⁓ renewal cycle. But from a scale,

scaling standpoint, can't do that with 5,000 customers. So the next segment down, we've got a hybrid approach. And in that scenario, it's really set up to give our customers the resources that they need at the right point in their customer journey, and also make those resources available to them when they want to have it as well. So it's more of a one to many, and it's a hybrid touch model, but it seems to work quite well, and our customers are still getting a lot of value from it.

Yeah, so I think there's a couple of, there's a lot that goes into this, right? I think the first thing that needs to be considered is are you making this change for existing enterprise businesses? Because at that point, it does become potentially contentious between sales and success, right? If you take a massive enterprise account that the sales... Okay. If the answer is yes, then I think...

What's really important there is mapping out that account and working with the sales team in making sure that sales and success are aligned to be able to Execute on the mapping that that is done. So if you get a large enterprise account, you're working with ⁓ One two three departments there and have an opportunity to sell additional products or two additional teams there

⁓ I think the success and the sales team have an opportunity to work hand in hand to pull in those stakeholders from the other organizations and work together. And then it's just a question of how ⁓ everybody is compensated for those expansions.

Mark Petruzzi (24:56)

Yeah.

Jack Zimnavoda (25:28)

Yeah, absolutely, it applies. We go through sales stages ⁓ that we essentially stole from sales. We've got our own pipeline that we're using to manage those opportunities and make sure that they're going from stage to stage in ⁓ the time that we expect it to, and that they're meeting the med-pick ⁓ kind of results that we need to along the way. So it's not all that different from sales. ⁓

Mark Petruzzi (25:38)

Thanks.

Jack Zimnavoda (25:57)

It is just a matter of where in the business we're doing this and when in terms of the relationship we're doing it. So we're always on the lookout for those opportunities and we're always going to capture those opportunities in our CRM or in our CSP and we'll be tracking them just like sales would.

Mark Petruzzi (26:18)

Great. Perfect. All right. Let's move on to topic three here, partnering with sales, product and marketing for good market impact. So, all right. So how, you know, what does good or great look like here from the standpoint of collaboration between CS and sales? And how do you avoid channel conflict when you still, you know, when you have to own that expansion side within CS?

Jack Zimnavoda (26:45)

Right.

So I guess I'll start with the second half of that question, which is avoiding channel conflict, right? And I think it's such an important question because it's totally normal for conflict to exist when this is introduced to an organization where historically sales has zoned expansions, right? ⁓ And again, in my experience, this happens because of one, possibly two reasons. The first is, you know, the swim lanes are not set and not made clear.

to both teams early on. And the second is compensation misalignment. So when you're talking about what good looks like, in my mind it's regardless of whether or not everybody's happy, because listen, there's always going to be people that wish things looked differently. But regardless of if everybody's happy or not, everybody at least understands the rules of the game. There needs to be clear rules of engagement for existing customers.

⁓ Again, just going back to my team, there are two very specific scenarios where the customer success team knows that they're not going to get credit for an upsell. Those scenarios are if it happens within a certain timeframe of the business closing, or if the expansion opportunity has already been charted out by the salesperson during the sales process with a set timeline in play. But the other part, again, is compensation misalignment.

Nobody wants to take money out of anybody's pocket. We're not trying to take money out of the sales team pocket. But again, in the vast majority of cases that I've been involved in, this territorial feeling about these opportunities don't necessarily mesh well with the data. Meaning that when you take a look at where salespeople are getting paid from, it's really far outweighed by the new business that they're...

bringing on versus upsells at existing companies.

Mm-hmm.

Yeah, in so many ways. And this is really a core responsibility, I think it always has been, of customer success. And there's a number of ways that this happens. ⁓ One of which is, just like with big whales during the sales process, there's gonna be some customers just like there are some big prospects that are just too large to fit. The big players who, if they say jump,

I'm just starting to jump. don't even ask how high because, you know, they just need that. ⁓ But, you know, those are, think, are a few and far in between, right? I think the more common scenario is that, you know, features get asked for through every stage of the customer lifecycle journey, know, from, you know, even before the sale is complete to onboarding, engagement, renewals, and

I think it is absolutely the customer success team's responsibility to capture those requests and also to help the product team prioritize those requests and enclose the feedback loop with customers. So internally for us, use a solution called product board that allows us to create a running list of who's asking for what and that feeds to the product team so they could do their work on prioritization. But on top of that, we meet with the product team

⁓ at least bi-weekly, where we tell them what we're seeing in the field, what we're hearing from customers, both large and small, and where we think we can make an impact from a product standpoint that'll add value both to existing customers, but also prospects in the pipeline.

Absolutely when we have those bi-weekly calls with product, it's my entire team that's involved.

It takes some time, but it's a well worth ⁓ while exercise.

Mark Petruzzi (31:11)

Perfect, so Jack, so let's cover off on the third part here of go to market and that's marketing. What has been your experience? What are the best ways to involve marketing and the post-sale customer journey and the overall adoption side of the equation as well? How do you keep them integrated?

Jack Zimnavoda (31:30)

Yeah, I think that's a massively important question because I think a lot of leaders look at this incorrectly in my view, my humble opinion. I think it's so natural for business leaders to think of marketing as solely a top-of-funnel function that's really exclusively focused on pre-sales impact. And frankly, I think it's a huge missed opportunity. So for Insightful, know, just last week, we blocked off almost the entire week

⁓ in one of our offices where members of the customer success team worked hand-in-hand with marketing to do a full gap analysis of our communication strategy post sales. And yeah, this included everything from welcome email communication to renewal notifications, but what I think really relevant to our conversation today is that we're also focused on how we can educate our customers on new features, new products, as they come out. ⁓

in mass so that our customer success team has a real shot of drawing interest before we even reach out individually for those conversations.

Mark Petruzzi (32:40)

Yeah, you know, that's something that we at at AGS think about a lot. Pretty much everything is marketing, right? Every interaction with a client in the way we look at it is either increasing or decreasing their perception and their opinion of the company. And very few things leave it where it was before. There's always a there's always a measure either direction.

So I love that idea of just making sure that you just go through that process that you guys did where marketing is in the middle of these relationships after they become clients. Because as we know, there are certain perspectives in marketing that they just kind of, that's not my job anymore from that perspective.

I totally agree that it is always their job and really every interaction is marketing one way or another.

Jack Zimnavoda (33:41)

I

totally agree. Just like, you know, everybody's responsible for the company's marketing. think to some extent, everybody's responsible for customer success as well, right? That case could be made across the board.

Mark Petruzzi (33:51)

Yeah, yeah.

Jack Zimnavoda (34:02)

So I consider myself extremely lucky that my work bestie, if you will, is ⁓ the head of lead generation. ⁓ So while we don't typically have regular syncs, ⁓ although there are probably monthly syncs that we have with marketing operations, ⁓ I also sit directly across from Alex and we work incredibly closely together.

She is far more entertaining than I am, so I highly recommend.

Mark Petruzzi (34:37)

That's excellent. All right, let's move to our final topic here, metrics and models that power scalable CS growth. So tell us about, what are the must-track metrics for any customer success leader who wants to be seen as a revenue leader as well?

Jack Zimnavoda (34:55)

Yeah, so there are a couple of no brainers here, right? ⁓ The one that comes to mind first and foremost is net retention. ⁓ Again, that's going to factor in expansion revenue, but it also bounces out with revenue churn that happens in the business. So, ultimately, if you're tied to number as a revenue leader, ⁓ it's going to be expansion revenue. ⁓

On top of net retention, just like any sales leader, and I mentioned this in a previous answer, just like any sales leader, I've got a pipeline that I manage. And I'm looking at conversion rates across the stages. I'm taking a look at where things are held up in the sales pipeline for expansion opportunities. And then lastly, I think, you know, metric that all go-to-market leaders should be looking at is customer lifetime value, right? CLTB. ⁓

You know, think, you know, this is something that that myself, our CEO is tracking really closely to ensure that not only are we able to sell to our existing customers and grow that account from a revenue perspective, but what we're selling is relevant enough to them that they retain our offerings over a longer period of time.

Yeah, absolutely. So, you it spoke a little bit about the importance that I feel predictive AI has on customer success. And I think that is, you know, this is clearly a good use case for it is incorporating it into health scores. ⁓ And, you know, I get that AI is a new tool and not everybody has a tech stack that allows them to incorporate this. But yeah, it's really, really powerful. ⁓ Short of that.

Yeah, we do take a look at usage trends. We take a look at specific engagements with the product that kind of signal that an account is adopting well or that they are engaging as often as we expect. But I'd also say that qualitative data is your friend when it comes to health scores. There's no problem.

in my mind, of relying on things like the opinion of the customer success manager via a rag indicator or a happy face or a sad face, right? It may not be spot on 100 % of the time, but when you use it in conjunction with that quantitative data like product usage, NPS scores, whatever else you have, it becomes a really valuable data point.

Yeah, so we're hoping to embed AI into our customer success platform, which for those that are not in customer success, CSP or customer success platform is essentially a CRM, but more focused on the post sales motion, right? And what we're doing is we're using AI to take a look at data points that are coming from different sources. So product usage trends, the MPS scores.

the notes that are taken by the CSM, whether it's taken through a system like Gong or it's manually typed in by a CSM. And it's able to aggregate this information over a course of time, provide insights as to not only is this account healthy, like going into the health score, but also what are some next steps that AI would recommend that you go through with this account? Are they at risk? And if so,

what can you do to minimize that risk? Or are they doing great and by the way because of the industry they're in, this may be an interesting use case where you could find some expansion opportunity. So, I'm sorry.

I would say that we are using predictive AI from a forecasting standpoint less on the expansion side and more on the retention side. I'm using it to forecast, you know, there's always going to be some level of churn at a SaaS organization. It's a painful truth. ⁓ But it's important for us to understand, you know, how leaky is that bucket and what do we have to do on the sales side to make up for it.

Mark Petruzzi (40:25)

So Jack, as you grow like you guys have been growing, what do need to do to evolve the CS structure or the overall operating model to support this new scale?

Jack Zimnavoda (40:40)

Yeah, scalability is an issue, right? ⁓ I think I mentioned when I joined Encyphe, maybe I didn't mention this, I apologize. ⁓ The customer success team that was here was really just focused on the top revenue accounts. And that meant that they were only engaging really with the top 2-3 % of our customer base. So I think in order to make this work when you're a larger company and are growing at the rate that we are,

Segmentation and putting in hybrid touch models where it makes sense ⁓ really matters. And the goal there is not to take away personalization, but to add tools that will allow you to offer personalized messaging and value without having to focus on just the top piece of that iceberg of your client accounts.

So for us, that meant doing a hybrid touch model like I spoke about earlier.

Mark Petruzzi (41:50)

Sure, let's do it. And Jack, that's our rapid fire question. So we'll move pretty quickly through these. A little different for you in the CS function, but what was the first product you ever supported? And then have you ever sold directly at any part of your life or career?

Jack Zimnavoda (42:07)

Yeah.

Yeah.

Yeah, my first job directly out of college was I was recruited as a financial advisor in Taston. That's really just a sales job. have a brain on new. Um, the timing of that was interesting. Four months later, Lehman Brothers failed and we entered the financial crisis of 2008. So great.

Mark Petruzzi (42:23)

Yes.

Jack Zimnavoda (42:37)

as quickly as I could,

It wasn't our fault.

Not so far off.

So does it have to be CEO? Okay. Yeah. I follow Daphne Casa Lopez. She's the global director of customer success at HubSpot. She also hosted a wonderful podcast called This is Growth. And I just think her insights are so spot on all the time. She's wonderful.

Mark Petruzzi (43:28)

Very cool. Yeah. Okay. What is a tool that you believe every CS leader should be using?

Jack Zimnavoda (43:36)

Yeah, so definitely a customer success platform. take your pick. There's Vitaly, GameSight, think Tatango, although I think they merged with somebody, TurnZero. ⁓ I'm a huge fan of Vitaly. That's what we're using here at Insightful, and it's been going very well for us.

man. ⁓ yeah, I would say I would tell myself to prioritize results over recognition. think, you know, when you're young in career, you want to get some kind of recognition, but, ⁓ especially when you're young in career, it really doesn't matter all that much. ⁓ that, comes later, right?

Mark Petruzzi (44:23)

That's pretty cool. Cool. And the last question is favorite book on customer success or growth or leadership.

Jack Zimnavoda (44:33)

Yeah,

easy one. The seven pillars of customer success. ⁓ I'm forgetting the author's name. It's by the former chief customer officer of Salesforce.

Mark Petruzzi (44:44)

So Chief Customs Officer, so I've done a lot of work with Salesforce. I'm wondering who wrote that one. I wonder if it's Mike Milburn, would that, not him? Okay, interesting. Yeah, no worries on that. We'll make sure on the show notes that we tie it to the right area. And again, I just wanna say,

Jack Zimnavoda (44:55)

I don't believe so. I could look it up.

Mark Petruzzi (45:10)

Jack, this has been a pleasure. Thanks so much for joining us and spending some time together. KK, thanks for being a part of this as always and to that incredible audience that we have. Thank you for joining in again.

Jack Zimnavoda (45:26)

Thanks so much for having me, I really appreciate it.

Mark Petruzzi (45:30)

Awesome. All the best. Bye.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode, co-host Mark Petruzzi welcomes Jack Zimnavoda, Head of Customer Success at Insightful. Jack shares how modern B2B SaaS organizations can turn customer success from a support function into a true driver of revenue and retention.

Together, they explore what it takes to align CS with sales, marketing, and product—without creating channel conflict. Jack reveals how predictive AI, smart segmentation, and aligned incentives can turn expansion into a scalable and proactive motion.

What You’ll Learn

• Customer Success as a Revenue Driver: Jack explains how to reframe CS from a cost center to a growth engine—through structure, ownership, and incentives.
• Avoiding Channel Conflict: Learn how clearly defined swim lanes, compensation clarity, and collaboration between CS and Sales create harmony and momentum.
• Building a Scalable CS Model: From white-glove enterprise accounts to hybrid-touch models, Jack outlines how to maintain personalized value delivery at scale.
• Metrics That Matter: Understand the importance of net retention, lifetime value, and how CS teams can build pipelines and forecast revenue just like Sales.
• AI + Customer Health: Hear how Jack uses predictive AI to monitor product usage, signal risk, and surface expansion opportunities at scale.

Key Topics

• Structuring CS to own post-sale revenue
• Aligning CS, Sales, Marketing, and Product
• Channel conflict: where it happens and how to prevent it
• Using AI in CS forecasting and health scoring
• Segmenting your customer base to drive upsell plays
• Scaling without losing the human touch
• How to hire for commercial CSMs (hint: curiosity and creativity)

Guest Spotlight: Jack Zimnavoda

Jack is Head of Customer Success at Insightful, where he leads a global team focused on retention, adoption, and expansion. With over a decade of experience in B2B SaaS, Jack has helped transform CS into a proactive, commercial function that partners across the go-to-market org to drive real business outcomes.

Resources & Mentions:

• Book: The Seven Pillars of Customer Success by Wayne McCulloch
• Podcast Mention: This is Growth by Daphne Costa Lopes
• Tool: Vitally – CS platform used by Insightful

🎧 Listen now and follow Selling the Cloud for more expert insights on scaling GTM teams. Subscribe wherever you get your podcasts.

Mark Petruzzi (00:04.705)

Welcome to today's episode of Selling the Cloud podcast. We're thrilled to welcome Jack Zimnavoda, Head of Customer Success at Insightful. Jack is a seasoned CS leader with a deep passion for helping companies retain and grow their customer base through intentional customer success strategies. He has built teams that drive renewal, expansion, and adoption at scale, and he's helped shape

how modern B2B SaaS companies think about customer-led growth. Today, Jack will explain how customer success can become a core growth engine through better cross-selling, upselling, and alignment with the rest of the go-to-market organization. Today, we'll explore four areas. One, we're thinking customer success as a revenue driver. Two, building a customer-centric expansion motion.

three, partnering with sales, product, and marketing for go-to-market impact, and four, metrics and models that power scalable CS growth. All right, well, again, Jack, welcome. We're very excited about having you here, and we can kind of kick off into topic one. But again, first, welcome.

Jack Zimnavoda (01:20.93)

Thanks so much. Really, really excited to be a part of this podcast and ready to dive into it.

Mark Petruzzi (01:26.807)

Perfect, all right. Topic one, rethinking customer success as a revenue driver. That is something that I have been in the middle of for many years. And it's funny, you get all different views on this straight up to the CEO and the board. You have a typical customer success mindset of, I don't wanna be selling, I'm not sales. But at the same time, that's evolved as we all know how important

the upselling and cross-selling process is and how that can't be done successfully without the support of the CS team. So Jack, know, CS has been viewed as a post-sales support function in the past. What needs to change in mindset and structure for it truly to become a revenue driver?

Jack Zimnavoda (02:20.609)

Yeah, so it's a totally fair mindset that go-to-market leaders have there of customer success being an offshoot of support, particularly for leaders that have been around in go-to-market leadership for 20 plus years, because truth be told, customer success was an offshoot of support. I started in this career back when it was account management, and then it's gone into its own...

know, evolution since then. But also, I think it's fair to say that that gap in the understanding of customer success being a support function versus what it's really intended to be these days is narrowing, right? I think these days, customer success, especially at SaaS firms, is kind of a core piece of the go-to-market team. And I think most people don't view it the way that they might have 15, 20 years ago.

In those instances where it is still viewed as a higher level of support, think really what needs to happen is a change in mindset first. And that doesn't happen by somebody saying, this works well at other companies, we should do it. I think it kind of happens by experimentation, right? Letting the customer success team go to their customers and offering new things to them, whether it's new use cases or

expansion to different teams or through different product offerings. And the proof is in the pudding in those cases. So I think with that experimentation, when you show small wins like that, it automatically changes the mindset. And once that happens, you could think about changing the structure of teams.

Jack Zimnavoda (04:43.532)

Yeah.

Jack Zimnavoda (05:17.42)

Yeah. These are really, you know, very real problems that customers have, or sorry, companies have when they start introducing customer success as a revenue generator, right? The truth is there's no one way that this works well. I've seen it done in so many different ways. I've seen pods created where CSMs are coupled with salespeople. I've seen, you know, customer success managers own all revenue operations post the initial point of sales and own a quota.

And I've even seen, you know, and I don't recommend this, I've seen CSMs essentially treated as SDRs to go out and find opportunities and feed them back to the sales team to manage. You know, I'll just speak to the way that my team is set up because I think it works quite well in the way that we're working it today, which is that my team, the way that that insightful works is that the sales team has a certain period of time whereby they're able to expand the accounts that they bring in.

But if that period passes, then the success team has the obligation really to nurture those accounts, find opportunities to take them from identification of the opportunity all the way through through close. And really we incentivize the team to do exactly that. So ultimately, I think any of those types of structures can work. It's just a matter of ensuring that incentives are aligned and that expectations between the teams are

very very clear.

Mark Petruzzi (06:51.86)

Great. So Jack, where do you see most companies going wrong when they're trying to turn customer success into a profit center instead of a cost center?

Jack Zimnavoda (07:02.987)

Yeah, great question. Two things every time. The first thing is that there's a lack of understanding sometimes when you want the customer success team to take on the ownership of the revenue. Lack of understanding of what the CSM team has on their plate already from a responsibility standpoint. And then blindly thinking that they could add opportunity, identification, and realization.

without negatively impacting those other areas that are already on their plates. So I think when you look at bringing this into a customer success team for the first time, it's really crucial that there's a plan in place to offload some of that non-value added work prior to making the shift so that hopefully the customer success team has a bandwidth to focus on this area plus the core competencies that they've always had.

I would say the other thing, and I mentioned this in the previous answer, which is not aligning incentives to the intended outcomes. So, you know, if you're starting this out and you've got your customer success managers judged on things like client sentiment or the number of quarterly business reviews they're doing or gross retention, there's really no incentive for the CSMs to grab onto this opportunity for them with everything they've got.

And just bringing this once again back to my team. I handle this by giving them incentives in two ways. The first is by giving them quarterly bonuses that's based on that retention, which of course factors in expansion dollars, but is really rooted in retention. But then on top of that, there is a small commission opportunity, but they're focused on non-organic expansions, meaning these opportunities have to be identified.

by the CSM, they really have to be the ones responsible for drumming up this business and owning it from identification through close to get that commission.

Jack Zimnavoda (09:19.649)

Honestly, I have not dealt with that struggle too much. And the reason is we set expectations extremely clearly upfront. We explain why the business is going in this direction, which is ultimately to grow revenue business-wide. And also, for me, it's a matter of showing them the previous data. Most of the time, salespeople can get territorial over their accounts, and that's understandable. But when you take a look at their commission payouts,

I'd say nine times out of ten, the vast majority of their commission is coming from new business anyway. It's just kind of a mindset that needs to shift of, I should just be focused on new business and that's the key area that the company needs me to focus on and that I'm getting paid for.

Jack Zimnavoda (10:37.421)

So I think it should work together pretty seamlessly, right? think sales and customer success need to be working hand in hand. And that is regardless of if customer success is owning the expansions or not. There needs to be a very solid understanding, foundational understanding of what the accounts need, what their use case is, what are their goals that they need to achieve to be able to say, yes, this expenditure was worth it.

As long as you have those kind of key points in play, then the rest I think falls into play pretty naturally. Again, making sure that you're not overloading any particular team with so much that they can't handle their responsibilities.

Mark Petruzzi (11:22.775)

Cool. I've got one more on this to double down a little bit. What are the early signs, Jack, that you see that gives you the indication that a CS team is being too reactive instead of being able to make that jump over to the strategic side?

Jack Zimnavoda (11:42.55)

Yeah, that's a great question. For me, it's really simple. If we're finding examples of churn, customers leaving us, and they come as a surprise to the CSM, it is a clear cut sign to me that they're just too in the weeds of resolving issues that are brought to them and not taking the time to have proactive conversations with their customers about what their goals are, what kind of value they expect to see. Any time that that

churn is brought up and we don't know what's going on there. I need to take a step back and I want my team to take a step back to really understand what happened there in terms of their involvement with that account because it shouldn't be a surprise.

Jack Zimnavoda (13:19.477)

Yeah, think there are a couple of things that are constant, whether it's a new logo or an expansion, right? Those things are, you know, solid understanding of what levers there are to pull for increases or expansions, right? Is this a play to sell professional services or is it add-ons that are available to them? Just understanding, you know, what's in their tool belt that they can rely on. And the other thing that I think is a constant between

whether it's an existing customer or a new customer, is a really solid understanding at the very minimum of the industries that you're serving and what challenges they're facing. Even better, obviously, if you have a solid understanding of the customers specifically and what their challenges are. But then there are things, I guess you call them ingredients, right, that are a bit more unique to existing customers.

The first is incredibly simple but incredibly powerful, think, and that is, are they a happy customer? You can have great products, you can have a really solid process for onboarding those customers, but at the end of the day, if a customer is giving you feedback that, for whatever reason, they're unhappy, maybe they're not able to achieve their goals or they felt that the onboarding process didn't work for them,

The focus can't be on selling that customer more at that point. It needs to be on fixing that problem. So I think there are a ton of signs that you could get for existing customers that you can't necessarily tell with a new, a net new account in terms of whether or not they're set up for a good expansion conversation. And then the other thing, the other ingredient I would say that's really great to have. I don't think it's a must have, but it's...

certainly nice to have, is there's no shortage of tools that a customer success team can rely on to know whether their accounts are primed for expansion. I'm a big proponent of using predictive AI tools that help you analyze the conversations that are happening between the CSM and the account that are able to take a look at the data in your customer success platform or in your CRM.

Jack Zimnavoda (15:37.614)

and predict whether or not this account based on a lot of their traits or whatever are a good candidate for expansion. When you're a company like Insightful where you've got 5,000 customers plus, don't have time, or the CSMs don't have time to sort through all the data on their own. So having that kind of predictive insight is really valuable in using their time wisely and focusing on the accounts that are

you know, really ready for that expansion conversation.

Jack Zimnavoda (16:15.541)

I'm sure there's more, I'm I'm blanking out the others.

Mark Petruzzi (16:19.671)

So Jack, tell us about how you work on training CSMs to have these types of commercial conversations without turning them into full-fledged sales reps.

Jack Zimnavoda (16:32.331)

Yeah, I think part of it doesn't really go into training. It comes into hiring the right people. And what I mean by that is, you know, when I'm hiring for CSM roles and I just actually had a couple of interviews this week for a new CSM role in New York, the two kind of mindsets that I'm looking for that I think are great for this position are curiosity and also creativity.

I think when customer success managers can go into conversations with the mindset of genuine curiosity about, you know, customers' businesses, you know, how they're making money, what their challenges are, and also creative approach towards problem solving for those challenges, conversations that lead to upsells or cross-sells really just happen naturally. So I think that's the first piece of it, is hiring for the right...

sets of soft skills, if you will. Having said that, there's also tactics that we could train on. One of those tactics for my team is when we're running quarterly business reviews, before that takes place, I'm having my team do a lot of research on the accounts that we're working with outside of just the departments we're working with. We're trying to identify stakeholders that may not even know about Encypheal, could find value in it.

And then we're going back to our champions and we're saying, Hey, let's bring them into the quarterly business review so they could understand what we're doing with XYZ firm. and it's just a very natural conversation. So I think, you know, we have the benefit of being able to have these non-sales conversations, that very naturally go into a direction of expansion in one way or the other.

Jack Zimnavoda (18:46.413)

Yeah.

Jack Zimnavoda (19:00.373)

And also I double down on that. think that serving and selling are absolutely not mutually exclusive. I think in order to serve, sometimes you need to sell and that's not a conflict of interest in my mind.

Jack Zimnavoda (19:22.188)

Mm-hmm.

Jack Zimnavoda (19:26.057)

Exactly, right? That's ideally that's what they're doing. Yeah

Mark Petruzzi (19:33.569)

So when you look at this overall, Jack, so what kind of role does customer segmentation play in the whole entire expansion strategy, the entire growth go to market?

Jack Zimnavoda (19:47.596)

Yeah, it's for a company like ours, it's massively important. You know, we've got, again, 5,000 customers across, know, across the globe, truly serving dozens of different industries. You know, if I were a CS leader of a company that sold a $5 billion product and only had 30 customers, it's not as important, right? Segmentation matters less in those instances. You just have to be insanely knowledgeable about each and every one of those.

businesses. But in cases where you have a larger customer base, yeah, absolutely imperative. We segment by customer size, their industry or vertical, what their potential use cases are. And these are really just goals when it comes to setting up expansion plays. The way that we handle, let's say, a massive organization that's only using us for one department is going to be

completely different than the way that we try to upsell a 300 person company that's already using it for all their employees. There's just different plays that are going to go into effect for each of those scenarios. But also the value propositions are going to be wildly different between these segments. There are some propositions that are going to be game changers for certain industries that are completely meaningless to others.

kind of summarize all that, the more that you can slice and dice your segments based on whatever you have, key traits, personas, use cases, know, whatever you have, the better your opportunities are to create messaging that is, at least feels personalized to your customers and can be done in a scalable way.

Jack Zimnavoda (21:43.15)

So right now our customer base is segmented mostly on revenue size. And yeah, we do have our enterprise segment, which as you might expect, is essentially white glove service with custom or bespoke onboarding, regular engagement through the adoption and renewal cycle. But from a scale,

scaling standpoint, can't do that with 5,000 customers. So the next segment down, we've got a hybrid approach. And in that scenario, it's really set up to give our customers the resources that they need at the right point in their customer journey, and also make those resources available to them when they want to have it as well. So it's more of a one to many, and it's a hybrid touch model, but it seems to work quite well, and our customers are still getting a lot of value from it.

Jack Zimnavoda (23:43.852)

Yeah, so I think there's a couple of, there's a lot that goes into this, right? I think the first thing that needs to be considered is are you making this change for existing enterprise businesses? Because at that point, it does become potentially contentious between sales and success, right? If you take a massive enterprise account that the sales... Okay. If the answer is yes, then I think...

What's really important there is mapping out that account and working with the sales team in making sure that sales and success are aligned to be able to Execute on the mapping that that is done. So if you get a large enterprise account, you're working with One two three departments there and have an opportunity to sell additional products or two additional teams there

I think the success and the sales team have an opportunity to work hand in hand to pull in those stakeholders from the other organizations and work together. And then it's just a question of how everybody is compensated for those expansions.

Mark Petruzzi (24:56.631)

Yeah.

Jack Zimnavoda (25:28.555)

Yeah, absolutely, it applies. We go through sales stages that we essentially stole from sales. We've got our own pipeline that we're using to manage those opportunities and make sure that they're going from stage to stage in the time that we expect it to, and that they're meeting the med-pick kind of results that we need to along the way. So it's not all that different from sales.

Mark Petruzzi (25:38.071)

Thanks.

Jack Zimnavoda (25:57.78)

It is just a matter of where in the business we're doing this and when in terms of the relationship we're doing it. So we're always on the lookout for those opportunities and we're always going to capture those opportunities in our CRM or in our CSP and we'll be tracking them just like sales would.

Mark Petruzzi (26:18.635)

Great. Perfect. All right. Let's move on to topic three here, partnering with sales, product and marketing for good market impact. So, all right. So how, you know, what does good or great look like here from the standpoint of collaboration between CS and sales? And how do you avoid channel conflict when you still, you know, when you have to own that expansion side within CS?

Jack Zimnavoda (26:45.783)

Right. So I guess I'll start with the second half of that question, which is avoiding channel conflict, right? And I think it's such an important question because it's totally normal for conflict to exist when this is introduced to an organization where historically sales has zoned expansions, right? And again, in my experience, this happens because of one, possibly two reasons. The first is, you know, the swim lanes are not set and not made clear.

to both teams early on. And the second is compensation misalignment. So when you're talking about what good looks like, in my mind it's regardless of whether or not everybody's happy, because listen, there's always going to be people that wish things looked differently. But regardless of if everybody's happy or not, everybody at least understands the rules of the game. There needs to be clear rules of engagement for existing customers.

Again, just going back to my team, there are two very specific scenarios where the customer success team knows that they're not going to get credit for an upsell. Those scenarios are if it happens within a certain timeframe of the business closing, or if the expansion opportunity has already been charted out by the salesperson during the sales process with a set timeline in play. But the other part, again, is compensation misalignment.

Nobody wants to take money out of anybody's pocket. We're not trying to take money out of the sales team pocket. But again, in the vast majority of cases that I've been involved in, this territorial feeling about these opportunities don't necessarily mesh well with the data. Meaning that when you take a look at where salespeople are getting paid from, it's really far outweighed by the new business that they're...

bringing on versus upsells at existing companies.

Jack Zimnavoda (28:49.165)

Mm-hmm.

Jack Zimnavoda (29:09.301)

Yeah, in so many ways. And this is really a core responsibility, I think it always has been, of customer success. And there's a number of ways that this happens. One of which is, just like with big whales during the sales process, there's gonna be some customers just like there are some big prospects that are just too large to fit. The big players who, if they say jump,

I'm just starting to jump. don't even ask how high because, you know, they just need that. But, you know, those are, think, are a few and far in between, right? I think the more common scenario is that, you know, features get asked for through every stage of the customer lifecycle journey, know, from, you know, even before the sale is complete to onboarding, engagement, renewals, and

I think it is absolutely the customer success team's responsibility to capture those requests and also to help the product team prioritize those requests and enclose the feedback loop with customers. So internally for us, use a solution called product board that allows us to create a running list of who's asking for what and that feeds to the product team so they could do their work on prioritization. But on top of that, we meet with the product team

at least bi-weekly, where we tell them what we're seeing in the field, what we're hearing from customers, both large and small, and where we think we can make an impact from a product standpoint that'll add value both to existing customers, but also prospects in the pipeline.

Jack Zimnavoda (30:57.449)

Absolutely when we have those bi-weekly calls with product, it's my entire team that's involved.

Jack Zimnavoda (31:05.99)

It takes some time, but it's a well worth while exercise.

Mark Petruzzi (31:11.553)

Perfect, so Jack, so let's cover off on the third part here of go to market and that's marketing. What has been your experience? What are the best ways to involve marketing and the post-sale customer journey and the overall adoption side of the equation as well? How do you keep them integrated?

Jack Zimnavoda (31:30.71)

Yeah, I think that's a massively important question because I think a lot of leaders look at this incorrectly in my view, my humble opinion. I think it's so natural for business leaders to think of marketing as solely a top-of-funnel function that's really exclusively focused on pre-sales impact. And frankly, I think it's a huge missed opportunity. So for Insightful, know, just last week, we blocked off almost the entire week

in one of our offices where members of the customer success team worked hand-in-hand with marketing to do a full gap analysis of our communication strategy post sales. And yeah, this included everything from welcome email communication to renewal notifications, but what I think really relevant to our conversation today is that we're also focused on how we can educate our customers on new features, new products, as they come out.

in mass so that our customer success team has a real shot of drawing interest before we even reach out individually for those conversations.

Mark Petruzzi (32:40.651)

Yeah, you know, that's something that we at at AGS think about a lot. Pretty much everything is marketing, right? Every interaction with a client in the way we look at it is either increasing or decreasing their perception and their opinion of the company. And very few things leave it where it was before. There's always a there's always a measure either direction.

So I love that idea of just making sure that you just go through that process that you guys did where marketing is in the middle of these relationships after they become clients. Because as we know, there are certain perspectives in marketing that they just kind of, that's not my job anymore from that perspective.

I totally agree that it is always their job and really every interaction is marketing one way or another.

Jack Zimnavoda (33:41.917)

I totally agree. Just like, you know, everybody's responsible for the company's marketing. think to some extent, everybody's responsible for customer success as well, right? That case could be made across the board.

Mark Petruzzi (33:51.093)

Yeah, yeah.

Jack Zimnavoda (34:02.775)

So I consider myself extremely lucky that my work bestie, if you will, is the head of lead generation. So while we don't typically have regular syncs, although there are probably monthly syncs that we have with marketing operations, I also sit directly across from Alex and we work incredibly closely together.

Jack Zimnavoda (34:31.287)

She is far more entertaining than I am, so I highly recommend.

Mark Petruzzi (34:34.999)

That's excellent. All right, let's move to our final topic here, metrics and models that power scalable CS growth. So tell us about, what are the must-track metrics for any customer success leader who wants to be seen as a revenue leader as well?

Jack Zimnavoda (34:55.103)

Yeah, so there are a couple of no brainers here, right? The one that comes to mind first and foremost is net retention. Again, that's going to factor in expansion revenue, but it also bounces out with revenue churn that happens in the business. So, ultimately, if you're tied to number as a revenue leader, it's going to be expansion revenue.

On top of net retention, just like any sales leader, and I mentioned this in a previous answer, just like any sales leader, I've got a pipeline that I manage. And I'm looking at conversion rates across the stages. I'm taking a look at where things are held up in the sales pipeline for expansion opportunities. And then lastly, I think, you know, metric that all go-to-market leaders should be looking at is customer lifetime value, right? CLTB.

You know, think, you know, this is something that that myself, our CEO is tracking really closely to ensure that not only are we able to sell to our existing customers and grow that account from a revenue perspective, but what we're selling is relevant enough to them that they retain our offerings over a longer period of time.

Jack Zimnavoda (36:40.619)

Yeah, absolutely. So, you it spoke a little bit about the importance that I feel predictive AI has on customer success. And I think that is, you know, this is clearly a good use case for it is incorporating it into health scores. And, you know, I get that AI is a new tool and not everybody has a tech stack that allows them to incorporate this. But yeah, it's really, really powerful. Short of that.

Yeah, we do take a look at usage trends. We take a look at specific engagements with the product that kind of signal that an account is adopting well or that they are engaging as often as we expect. But I'd also say that qualitative data is your friend when it comes to health scores. There's no problem.

in my mind, of relying on things like the opinion of the customer success manager via a rag indicator or a happy face or a sad face, right? It may not be spot on 100 % of the time, but when you use it in conjunction with that quantitative data like product usage, NPS scores, whatever else you have, it becomes a really valuable data point.

Jack Zimnavoda (38:12.395)

Yeah, so we're hoping to embed AI into our customer success platform, which for those that are not in customer success, CSP or customer success platform is essentially a CRM, but more focused on the post sales motion, right? And what we're doing is we're using AI to take a look at data points that are coming from different sources. So product usage trends, the MPS scores.

the notes that are taken by the CSM, whether it's taken through a system like Gong or it's manually typed in by a CSM. And it's able to aggregate this information over a course of time, provide insights as to not only is this account healthy, like going into the health score, but also what are some next steps that AI would recommend that you go through with this account? Are they at risk? And if so,

what can you do to minimize that risk? Or are they doing great and by the way because of the industry they're in, this may be an interesting use case where you could find some expansion opportunity. So, I'm sorry.

Jack Zimnavoda (39:58.792)

I would say that we are using predictive AI from a forecasting standpoint less on the expansion side and more on the retention side. I'm using it to forecast, you know, there's always going to be some level of churn at a SaaS organization. It's a painful truth. But it's important for us to understand, you know, how leaky is that bucket and what do we have to do on the sales side to make up for it.

Mark Petruzzi (40:25.889)

So Jack, as you grow like you guys have been growing, what do need to do to evolve the CS structure or the overall operating model to support this new scale?

Jack Zimnavoda (40:39.629)

Yeah, scalability is an issue, right? I think I mentioned when I joined Encyphe, maybe I didn't mention this, I apologize. The customer success team that was here was really just focused on the top revenue accounts. And that meant that they were only engaging really with the top 2-3 % of our customer base. So I think in order to make this work when you're a larger company and are growing at the rate that we are,

Segmentation and putting in hybrid touch models where it makes sense really matters. And the goal there is not to take away personalization, but to add tools that will allow you to offer personalized messaging and value without having to focus on just the top piece of that iceberg of your client accounts.

So for us, that meant doing a hybrid touch model like I spoke about earlier.

Mark Petruzzi (41:50.497)

Sure, let's do it. And Jack, that's our rapid fire question. So we'll move pretty quickly through these. A little different for you in the CS function, but what was the first product you ever supported? And then have you ever sold directly at any part of your life or career?

Jack Zimnavoda (42:07.777)

Yeah.

Yeah.

Yeah, my first job directly out of college was I was recruited as a financial advisor in Taston. That's really just a sales job. have a brain on new. Um, the timing of that was interesting. Four months later, Lehman Brothers failed and we entered the financial crisis of 2008. So great.

Mark Petruzzi (42:23.063)

Yes.

Jack Zimnavoda (42:37.864)

as quickly as I could,

Jack Zimnavoda (42:53.909)

It wasn't our fault.

Jack Zimnavoda (42:57.901)

Not so far off.

Jack Zimnavoda (43:05.485)

So does it have to be CEO? Okay. Yeah. I follow Daphne Casa Lopez. She's the global director of customer success at HubSpot. She also hosted a wonderful podcast called This is Growth. And I just think her insights are so spot on all the time. She's wonderful.

Mark Petruzzi (43:28.353)

Very cool. Yeah. Okay. What is a tool that you believe every CS leader should be using?

Jack Zimnavoda (43:36.523)

Yeah, so definitely a customer success platform. take your pick. There's Vitaly, GameSight, think Tatango, although I think they merged with somebody, TurnZero. I'm a huge fan of Vitaly. That's what we're using here at Insightful, and it's been going very well for us.

Jack Zimnavoda (44:01.689)

man. yeah, I would say I would tell myself to prioritize results over recognition. think, you know, when you're young in career, you want to get some kind of recognition, but, especially when you're young in career, it really doesn't matter all that much. that, comes later, right?

Mark Petruzzi (44:23.831)

That's pretty cool. Cool. And the last question is favorite book on customer success or growth or leadership.

Jack Zimnavoda (44:33.163)

Yeah, easy one. The seven pillars of customer success. I'm forgetting the author's name. It's by the former chief customer officer of Salesforce.

Mark Petruzzi (44:44.535)

So Chief Customs Officer, so I've done a lot of work with Salesforce. I'm wondering who wrote that one. I wonder if it's Mike Milburn, would that, not him? Okay, interesting. Yeah, no worries on that. We'll make sure on the show notes that we tie it to the right area. And again, I just wanna say,

Jack Zimnavoda (44:55.103)

I don't believe so. I could look it up.

Mark Petruzzi (45:10.559)

Jack, this has been a pleasure. Thanks so much for joining us and spending some time together. KK, thanks for being a part of this as always and to that incredible audience that we have. Thank you for joining in again.

Jack Zimnavoda (45:26.743)

Thanks so much for having me, I really appreciate it.

Mark Petruzzi (45:30.165)

Awesome. All the best. Bye.

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