Selling Intelligence (formerly Selling the Cloud)

In this episode of Selling Intelligence Podcast, Mark Petruzzi and KK Anderson sit down with Sunil Rao, founder and CEO of Tribble, to explore how AI is reshaping enterprise sales, go-to-market execution, and the future of software itself. Sunil shares why AI-driven productivity alone is no longer enough to create advantage, how the rise of agents is changing what software should do, and why trust, personalization, and institutional knowledge are becoming even more important in a world flooded with AI-generated noise.

The conversation dives into the productivity paradox, the coming consolidation of fragmented SaaS tools, and the shift from software that assists humans to systems that can actually take action on their behalf. 

What You’ll Learn:

• The Productivity Paradox: Why AI makes everyone faster at the same time, raising the bar instead of creating instant advantage.
• AI and New Work Creation: How efficiency gains in one part of the workflow can create new review, oversight, and decision-making work elsewhere.
• Differentiation in an AI World: Why personalization, timing, and relevance matter more now that everyone has access to the same tools.
• From SaaS to Agents: What separates AI-assisted software from agentic systems that can actually do the work.
• Trust in Autonomous Systems: Why transparency, confidence, and clear decision logs are critical when AI operates inside core business systems.

Key Topics:

• The treadmill problem in modern sales productivity
• Why AI has upgraded everyone at the same time
• The flood of low-quality outbound and the need for precision engagement
• Using digital exhaust and customer signals to guide better sales conversations
• Why traditional scaling models relied on people because software could not solve the problem yet
• How fast-moving foundation models are changing product design
• The coming consolidation of SaaS point solutions
• Why the future interface may be lighter, with more approvals and fewer manual workflows
• Building AI-native products that can evolve with each new model release
• Reducing SaaS fatigue by designing for orchestration, not more app sprawl

Guest Spotlight: Sunil Rao

Sunil Rao is the founder and CEO of Tribble, an AI-native platform built to help enterprise sales teams scale knowledge and automate critical go-to-market workflows. Before founding Tribble, Sunil began his career as a software engineer at SAP and later held leadership roles at Salesforce, including GM of Consumer Goods. Tribble was founded in 2023 and has quickly gained traction for helping companies automate RFP responses and improve GTM efficiency with AI-native workflows. 

Resources & Mentions:

• Tribble
• Salesforce Ventures generative AI fund
• RFP automation and response workflows
• AI agents versus traditional SaaS applications
• SaaS consolidation and platform orchestration
• The role of trust and transparency in AI adoption

🎧 Listen now and follow Selling Intelligence Podcast for more conversations on AI, modern go-to-market strategy, and the future of enterprise sales.

Mark Petruzzi (00:31)

Welcome to today's episode of Selling Intelligence Podcast. I'm thrilled to welcome Sunil Rao, founder and CEO of Tribble, an AI native platform that's fundamentally changing how enterprise sales teams scale knowledge and automate critical go-to-market workflows. Sunil's journey has been fascinating. He started as a software engineer at SAP.

moved into leadership roles at Salesforce, including and general manager of consumer goods, and then founded Tribble in 2023. Tribble was quickly added to Salesforce's ventures, $500 million generative AI fund, and has since revolutionized RFP automation, helping companies like Clary, Sword Health, and others slash response times by up to 80%.

Today we're exploring a critical challenge facing every sales leader. AI is making us more productive, but the bar keeps rising. It's like running on a treadmill at full speed and just when you your stride, the incline keeps going up. How do you stay ahead when everyone else has access to the same productivity gains? We're gonna focus on four critical themes. The productivity paradox, why AI-driven efficient

isn't enough to win anymore. From software to agents, building AI that actually does the work, not just assists, scaling institutional knowledge, the hidden competitive mode in enterprise go-to-market, and the human element, where AI should take over and where it must step back. Sunil.

First off, we're really happy to have you here. Thank you for taking the time with us and welcome.

Sunil Rao (02:10)

Thanks for having me. It's nice to be with you all.

Mark Petruzzi (02:12)

Excellent. So topic one, the productivity paradox. Let's start with what you have called the treadmill problem. Every sales team now has access to AI tools, chat GPT, co-pilot, all these niche engagement and enablement platforms. And all sales teams are getting more productive, or at least the ones that are investing in this. But here's the thing, if everyone's running faster, you're not actually getting ahead. You're keeping up with the pack.

And worse, buyers' expectations are rising because they know that you have these tools. So how do you think about this productivity paradox?

Sunil Rao (02:47)

Productivity paradox, it's interesting because I think there's a couple of ways that I like to think about it. You obviously have this tremendous technology. It's almost magical. It's been distributed to everyone almost simultaneously. And they're all able to see how much productivity it brings into all aspects of their job. But I back to beginning of when we started Tribble, and this is when Chat GPT has just come out, November of 2022.

And everyone had that aha moment of, whoa, this thing can write coherently for such a long time. It can actually write code. It can write snippets of code. And it just started to become a way for you to use in your workflow versus going to Google, searching for information. This thing can synthesize knowledge. So when you look at that and that impact,

It already was a tremendous time saver for a lot of smaller jobs. But I think what's been going on and what's been happening over the last few years with these foundation models getting better and better, it gets to the point now where these systems can run for hours on end and complete much more complex tasks. And that's where it's more interesting where, you know, what was not possible to solve with software three years ago.

is possible today. And that's where agents come in and everything comes in. it's interesting because like you have that happening in one side and it's really magical technology. But then at the same time, you kind of create new work.

when you have access to this technology, because now everyone's a creator. And I see this a lot in the engineering side. Everyone's writing more code, and then it's the question of who's reviewing it. If everyone's writing more content to go in documents, who is doing the human check? So you have this trade-off of, yes, there is efficiency in one part of the process, but you end up creating some work elsewhere. So I think it's the paradox, because it actually changes the distribution of where work is being done.

KK Anderson (04:30)

Really, really interesting. So when we think about it from, you know, a sales or revenue perspective, right? It's, you know, for, for so many years, it was, do you have this Salesforce CRM? Do you have this outreach, you know, program set up? Do you have this automation set up? And it was, you were always running to keep ahead and to keep up to pace with all of the different technologies that were available. And that was just sort of table stakes.

Right? And now with AI, as you just said, like everybody has it. And so now it's how you use AI is, is, and how you become a, differentiator using AI is the new game. Because otherwise it's this, we, you know, ⁓ as Doug Landis, one of our good friends and colleagues says is we're in a culture of sameness right now.

Sunil Rao (05:15)

Mm-hmm.

KK Anderson (05:16)

an era of sameness, I think is what he says. So talk to us a little bit about that. So now here we are, we all overnight got Chappie, GBT and these amazing programs. How do we differentiate ourselves in this world of AI?

Sunil Rao (05:30)

it's an interesting way to think about it, right? It's almost like everyone got upgraded, but exactly to the same level. So then how do you differentiate is the It's how do you stand out from the pack? And, you know, and I take the example of outbound and emails. Like I think what's happened, it's both a gift and curse.

KK Anderson (05:37)

Yes.

Sunil Rao (05:45)

I mean, I'd it's more of a curse because now there's so much garbage when it comes to outbound, right? In terms of mass generation of emails that are not personalized, that are not targeted. And I still think that the age old, you know, what makes you really good about that style of top of the funnel engagement is when you are very personalized and targeted. think that just actually gets even more amplified as an important way to stand out, right? Don't, don't try to sell something to the masses. Really think about what signals.

indicate that this may be a buyer that's interested and engage with them on the journey at the right time becomes way more important. Because otherwise, you're just feeding into the sea of noise that's being generated because we have these tools that can mass create this content. So I think there's that aspect of it. How can we be much more tailored on the engagement side? And I think about it at different parts of the funnel. For us at Tribble, we think deeply about this problem.

when we talk about our customers using our products and how they engage with their customers. So we look at it from two sides of that coin. Mark, you'd shared our respond product, which is all about responding to RFPs, responding to customers. You have to be very particular about what it is you do as a business, how you differentiate.

And that's informed by your conversations, your knowledge basis and all this stuff internally allows you to differentiate against your competition. But then on the engaged side, where we have software that helps BDRs, SDRs and others engage with their customers. Like we think really about what is the information that we have captured in all the digital exhaust with all the touch points we've had with this customer that indicate that this is in fact something that they're interested in. And how can we in real time kind of guide that conversation and coach it? So we get to the.

And I think customers really want that level of detail and personalization because otherwise you're kind of feeding the sea of noise like you've said.

KK Anderson (07:29)

All of a sudden to be human is to be cool.

Mark Petruzzi (07:30)

Yeah.

Sunil Rao (07:32)

I mean, I think people are

purposefully putting spelling mistakes in LinkedIn posts because it's like now become a sea of, and you see it, right? When you look at the posts and you see the dashes, the end dashes or the dead giveaway of ChatGP, everyone's using them now.

KK Anderson (07:43)

yeah. The dashes,

Mark Petruzzi (07:44)

100

KK Anderson (07:45)

I can't, emojis make my blood curl now. I'm like, ⁓ you know?

Sunil Rao (07:50)

KK,

like, here's a funny question. I actually thought about this the other day. I actually don't know how to type the dash on the keyboard. So it's like, where is it coming from?

KK Anderson (07:55)

I don't know.

Mark Petruzzi (07:56)

That is great. You know what, Sunil, when you mentioned the top of funnel and what's happening there, that's an area that KK and I spend a lot of time with our clients to make sure that they don't fall into this AI paradox where five years ago, before we were in the,

KK Anderson (07:57)

really don't? That's awesome!

Mark Petruzzi (08:18)

Gen. AI era before it even had a name. You saw that there was so much outbound going to prospects and customers. And what we found is there's been more damage in that than benefit in a lot of companies, meaning they are pushing more potential clients away than in some cases they're ever bringing through the door.

So taking you back to your time at Salesforce and when you were running your go-to-market operations initiatives there and seeing all the inefficiencies that were happening with customers of Salesforce but also right in with Salesforce as well, what was the breaking point for you that made you realize traditional approaches to sales productivity were just fundamentally broken?

Sunil Rao (09:07)

You know, I think it's.

Once again, this comes back to the point earlier of what is now solvable by software simply wasn't solvable five years ago, right? So what did you do? The problem was solved by hiring humans and kind of building processes, building checks, building scaling functions, building these expert groups within the company that house knowledge that would scale the rest of the organization. You invest heavily in resources like that and all the supporting functions and resources to keep them going. And I think, you know, that

that goes far and frankly if you don't have the technology you have today, that's the only way to do it at the time.

For me, the inflection point clearly was the rate of change of the technology outside that was indicative that, hey, if I had to build a company from scratch today, I would probably not staff it the same way, given where tech is at this moment in time. That was 2022, right? And then you go forward in time one year, the number of people factors down even further because the technology is now improving at an exponential rate. And you fast forward another two years and it's crazy how fast things are moving. So I think, like I would say

the tools and capabilities and what it is that you are building from a scaling standpoint, as more is becoming available outside, really how quickly can you factor that into the organization and how quickly can you grow? Like this has to be top of mind for every executive at every company right now, right? And I think that that is changing at such a fast pace that folks are just open to having those conversations now and like really thinking, how do we build this differently?

KK Anderson (10:32)

And it, does it become less fragmented? Right. Or more fragmented. You're adding in, there's a big one million AI products and solutions out there. And there's one, you know, go to market inside this, this, this company. Right. Like, how do you even begin to look at and think about.

you know, how you're gonna weave in and out all of these products and how they're gonna talk to each other and I don't know, talk to me a little bit about that.

Sunil Rao (10:55)

Our thesis on this is there's a mass consolidation coming. And I don't think that that is a very unique point of view. I think most people realize it. The general purpose nature of the underlying technology serves itself very well to addressing many use cases. And what I mean by that is when we started the company, thought about a category and we were, the vision was always to do something much broader and go to market, but then you kind of say, hey, what's the thing I'm going to do tomorrow really, really well?

And we picked RFP. And the reason for that was it's a known problem. People knew how to buy software in that domain. And there's a lot of pain there. But that being carved out as a product category, and this is true for any other category of software, these are artificial boundaries created as, this is a category of software. There's a level of functional kind of capability locked in it, technical difficulty to enter it and build it.

But there's no reason sometimes these adjacent categories shouldn't be talking to each other. So think, KK, to your question, I think people will expect tools to do a lot more. Hey, I want you to be a tool that does x, y, and z, not I need a tool for each of these. I think the last decade with all this fragmentation of SaaS and so many point solutions, there's just fatigue in buying. And AI is now going to be a consolidation on top of that. Because the beauty of this technology is it can connect to the downstream systems and become the new interface on

top of several so it can orchestrate across them right and I think a lot of the companies that are building like us have that as an advantage.

KK Anderson (12:18)

Makes a lot of sense. let's take us into the second topic here from software to agents, just as you're talking about, and building AI that actually does the work and not just assists in the work. And you've made a very deliberate choice with Tribble, and you didn't build another SaaS app, right? You built an agent. ⁓ So talk to us about the fundamental difference between

AI assisted software and truly agentic AI. I think a lot of our audience and sales leaders would like to really understand that. And why does that distinction matter for go-to-market teams?

Sunil Rao (12:54)

I think there are a couple of implications of thinking about it. just to orient how I think about this and what we think about it at Tribble. Software up until the point where this new stack of technology, specifically LLMs, vector databases, and everything that goes into the new kind of architecture has historically been, you know,

You have a database and then you have a UX on top of that database and you have a whole bunch of workflow capability automation and even AI as it was, I it has been around forever, right? It just changes what it actually is. And that's been the way things have been built, but it really is predicated on this transactional data store on which a user interface exists for teams of humans to go operate. And

You know, lot of companies have done really well. And even my previous employer working at Salesforce, one of the things they did really well is they did the cloud first really fast. And I still remember when we were talking to customers 10 years ago, comforting them that the cloud was a safe place to put their data, right? Now that's, that's not a problem anymore because folks have like taken that modality as a good, it's a good way to scale subscription model makes sense. Software makes sense when you deploy it in the cloud. ⁓

and all of that stuff. So now what happens in the last three years is we've got technology that allows you to kind of short circuit some of those layers. So when we think about what is an agent-first product, well, what is the layer between where the data is stored and how it's served up to the user? And in which cases do you even need to serve it up to the user anymore? The entire idea of user interface for us, for us to go in there, see the knobs and dials, and change things.

Mark Petruzzi (14:20)

Thanks.

Sunil Rao (14:25)

I think that doesn't go away because obviously humans are in every company and they will continue to be for the foreseeable future. Then the question is, okay, what parts of that process maybe can we automate away where they don't need to see it, right? It doesn't get served up to the UX. So I think it changes the way you think about how you build these products because

when you have this broker in between you and where the data is stored, and you can rely on that broker to do some of the work for you, it's kind of like having a really, really capable employee that's going to do stuff and you trust them to do it. So like, if you had that as part of it, do you need to see a screen that's as busy? Maybe not. Do you maybe need to see as many screens? Maybe not. Maybe you just have approval buttons instead of actually seeing the detail every time. So there's these architectural implications in how you build the products. And I think, you

But the thing that also changes when you build it this way is when these foundation models, like these companies like Anthropic and OpenAI, they're moving at blistering speed. If your two model releases behind...

you're not harnessing like 60 IQ points of new capability. So how do you build a product that can seat itself on top of that innovation and harness it as it comes out? That's the way you have to build software in the future. Now, if you built it the old way and you sprinkle the new stuff on top, you still have to bring along the old stuff for the ride, right? And, you know, lot of big companies have very, very smart people. I've worked with many of them. And when you have a large customer base using the old stuff, it's really hard to just go to the new stuff.

Mark Petruzzi (15:25)

Hmm.

Sunil Rao (15:48)

have to think about how you bring the old stuff along for the ride, right? So I think that's the way I like to think about it. When you're AI native, you've been given the privilege to make some choices that allow you to move a lot faster. And this could also just be true of startups, right? think it's like we're seeing it at an accelerated rate.

KK Anderson (16:02)

It's a master class.

Mark Petruzzi (16:03)

and Sunil, of the things KK will tell you about working with me is that, and I know it myself, I'm always focused on productivity. I use that word too many times in a day. And I've learned, having worked with many CEOs, having been a CEO myself, that you learn how these CEOs, some of them

get caught up into the process and the control access or the control aspect rather is the right word of being a CEO versus an enablement aspect and just a value add role. And it's going to happen, it is happening the same way with agents just as you described. So I love how you describe this, the agents,

have to be autonomous. This is not another form of automation. We're moving through much more productivity and ability to learn, get better, get smarter, do a particular job better. Now what I'm seeing now is a lot of customers and clients are looking at it and saying, okay, well, they're monitoring the agents. They want to see it just like a CEO that wants to be copied on

every email from every VP and up within a company. tell us a little bit about how you, like how do you feel that, how do you make that change? How do you get a client to look at this and say, I'm gonna be bringing these agents into your business with I know you're gonna have to do your due diligence and you're gonna have to really get confident in it.

But when you get confident in it, let them roll. Look at them just like human employees, just unfortunately for us humans, they're a lot more productive. They don't take a vacation. They work 24-7, we don't.

Sunil Rao (17:54)

You know, I think Mark, it's a very timely question and KK, I think you said something along these lines at the very beginning. Trust.

Right? Like it's never been more important and it's relevant to the fact that we have the sea of sameness, right? How do you trust that this is a real message meant for me? How do I trust that, you know, how do I trust this relationship from the very beginning? Are you just treating me as one of the many masses? I think that theme comes into even product strategy and how we think about where we show up with our customers.

So if you are going to use a product, especially if you're going to use a product that you give a level of autonomy to, and it's going to go in right against your master and your systems of records, you better trust it. So then it's like, okay, how do you build that trust? What kind of transparency do you put into the product? do you make it very clear? The log of decisions that were made, right?

Sunil Rao (18:40)

Makes sense.

Mark Petruzzi (18:41)

let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and many unused platforms. Yeah, you built the company in the enterprise software space to go right at that. How did you design Tribble to avoid becoming part of the problem and rather being part of the solution?

Sunil Rao (19:01)

I think one of the things we deliberately did in the early days was really think about like, where are things going, right? Just in the next three to five years, what do we think happens? If you go back to ⁓ the way back machine, which allows you to see kind of websites from.

can take look at Tribble's website in like December, 2023. had the headline, Kiss Your Apps Goodbye, Say Hello to Agents. And that was, founded the company in 2023, but it was very clear to us that, hey, this idea of having all these applications.

KK Anderson (19:23)

I love it.

Mark Petruzzi (19:30)

Cool, okay, so we'll jump in so let me go read that one again and we'll go and we'll do that question one more time.

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, Mark Petruzzi and KK Anderson sit down with Doug Landis to explore why storytelling has become one of the most powerful skills in modern sales. From lessons learned in the film industry to practical strategies for enterprise selling, the conversation highlights how narratives help sellers build trust, create alignment, and close deals faster.

Doug explains that buyers don’t actually buy products; they buy the story attached to the outcome those products create. When sellers focus on telling clear, meaningful stories rather than listing features, they make it easier for buyers to understand the value and communicate it internally. 

The discussion also dives into the shift from traditional inside-out selling (focused on CRM data and internal information) to an outside-in approach, where sellers study the buyer’s business, strategy, and external signals to craft a more relevant narrative.

What You’ll Learn

• Why storytelling is more powerful than product features in sales
• How great stories help buyers remember your solution and sell it internally
• The difference between rambling and effective storytelling in conversations
• Why sellers should shift from inside-out CRM preparation to an outside-in perspective
• How understanding your buyer’s business leads to stronger trust and bigger deals
• Why trust-driven selling can accelerate deal cycles and increase deal size
• Practical ways sales leaders can build storytelling into their team culture

Key topics covered include:

• How great stories help buyers sell your solution internally
• The difference between rambling and structured storytelling
• Why sellers should spend more time on outside-in research
• How AI tools can help sellers synthesize external insights faster
• What leaders can measure to prove trust-driven selling works
• Rapid-fire insights on sales habits, books, and early lessons

Doug also shares a powerful reminder: people don’t buy features; they buy the outcome the story promises, whether that’s solving a problem, improving their business, or simply getting their Sundays back. 

Mark Petruzzi (00:31)

Now that is some, that's really, really great stuff, Doug. And I'm gonna share a little bit about how I use, how I've learned to use stories into my selling process. And not only my selling process, running companies, working with private equity firms, communicating with people in all kinds of ways. And it really came down to about 15 years ago,

Doug Landis (00:45)

Mmm, yes.

Mark Petruzzi (00:56)

I was involved with a couple of ⁓ and brought in by friends of mine in a couple of films and TV series. I invested in a couple of them for a little bit of a while. was like, forget about enterprise software and selling. And I'm going to be running around with Steven Spielberg soon. That didn't happen. But we did pretty well with these movies.

And I'll give you an example. Somebody I've done work with is a filmmaker by the name of Michael Corente. And he's just one example of about a half a dozen that I got to work with. But he's a producer. That's what he focuses on. And in the entertainment industry, I learned there are no, well, there are, I found in my career, there are no better storytellers, not even than the writers. Of course they know how to tell stories.

Doug Landis (01:20)

So cool.

Mark Petruzzi (01:44)

but the producers that are out there getting investments and everything else. And man man, Michael was one of them. He's done some amazing things. He's created some really just incredible films that he made happen and he does a lot of stuff with Netflix now and Hulu and incredible stuff. So my point in this is for everyone in business,

Doug Landis (01:48)

Yep.

Mark Petruzzi (02:09)

Find your way of getting exposed to individuals like that. Now we all can't typically just call up and get to know a producer. I just happen to have some friends in the industry that I grew up with and got in that track. But maybe it's about writers. It's about different people who run businesses that you just look at. And just learn that side of the equation because

It's as specific as you define it, in my opinion, and it's also as generic as just like if you learn how to be a good storyteller, you're going to be successful in business and life. Like I use these same skills with my two children. they love to hear stories. It's just incredible. good.

Doug Landis (02:48)

Amen.

KK Anderson (02:49)

People will like you, Yeah.

Doug Landis (02:53)

Well, I got a caveat to that.

I have a caveat to that. Everybody loves somebody who is a good storyteller. Everybody despises somebody who not despise that's pretty aggressive, but it's not a big fan of the people who ramble. They think they're telling a story and they're just it's just one ginormous run on sentence that you never know where going to end. Because reality is it right like it's like no one wants to be the person stuck at the party with I ⁓ I got to sit next to them. ⁓ they never shut up. They always say

KK Anderson (03:09)

Yes.

1,000.

Mark Petruzzi (03:17)

Excel.

you

KK Anderson (03:23)

Is there any time?

Doug Landis (03:26)

All they do is talk your ear off or they just talk about themselves, right? They don't ask, they don't treat it as a conversation, right? So like, this is what happens. I mean, this is why I always think selling is just a series of conversations. We're having a conversation to see if it makes sense for us to have another conversation. And if so, who else should be involved? What's interesting is in conversations in everyday life, we tell stories, right? So like, just get better at being really clear and succinct about the story that you're trying to tell. And I think it's hard.

Mark Petruzzi (03:28)

Yeah. ⁓

KK Anderson (03:45)

Thank

Mark Petruzzi (03:45)

Yep. Yep.

Doug Landis (03:52)

Like I think it's hard to be able to do on the fly because you have to be really thoughtful. It's a muscle, like practicing your discovery muscle, just like practicing your negotiation muscle. These are muscles that you have to practice. ⁓ I love it.

KK Anderson (04:06)

And you gotta

get good at telling stories on the

Doug Landis (04:08)

And so you need to know what stories you need to know what stories are the best stories to go tell for this particular audience in this particular moment. Right. And so that's why I say like, if it's a first conversation with a with a prospect or a buyer, I need to be really thoughtful about what stories do I want to tell? What stories do I want to bring in the conversation? I'm thoughtful enough about what questions I'm going to ask. I'm thoughtful about what about what products I might talk about or, or, or maybe infuse into the conversation.

KK Anderson (04:26)

Right.

Doug Landis (04:34)

Why don't I just spend the extra minutes to be thoughtful about the story or stories I might want to tell in the conversation.

KK Anderson (04:39)

and practice it.

So I wanna also talk about what happens when we're not in the room as sellers with our buyers. We know that they have to turn around and very often, I mean, the last number I saw was like on average, anything over $25,000 would go to a CFO of all things. Like even people who've had buying authority and budget for...

Doug Landis (05:01)

Yeah.

KK Anderson (05:04)

most of their careers no longer do because of what's happening right now. And so who you're talking to, they have to turn around and sell it internally, they have to be your champion. And I will tell you, the stories are what they remember. So if they're gonna turn around and go talk to their coworker about it or get buy-in, they're probably going to be telling that story. Like, you told me the story, they'll be able to recite it.

Whereas like you said, the multiple choice question, like they're gonna be like, can't remember. I don't really remember what it does, but it sounded cool.

Doug Landis (05:32)

I can't remember which vendor actually says they can integrate with Salesforce or with, with all of that. I can't remember. Like honestly, even if I'm looking at two solutions, I'm like, shoot, I don't remember which one actually is like, yeah. ASC 2019 integrated like, well, I don't remember. Right. Cause they're all saying the same thing. By the way, here's the, here's a little, here's a little tagline. You can share with everybody. Well, if everybody listening, people don't.

KK Anderson (05:35)

Yeah.

Mark Petruzzi (05:44)

Jesus.

KK Anderson (05:47)

Yeah.

Doug Landis (05:58)

buy products. They buy the story attached to it. Right. It's connected to an outcome. It's like, Oh, this, if I, this is one of my favorites. we, we do a lot of work with Salesforce and MuleSoft and it's like, do know how many people are in the API integration world are working on Sundays because all of a sudden integration went down on Friday. And if it's not up and working on a Monday, then guess what? They're not actually doing transactions. Oh no. So

Imagine if you buy a solution like MuleSoft, you never have to work a Sunday again, now you can hang out with your kids. That's the story I'm telling you in my head as I'm trying to solve for this integration problem that I have. It's like, I want my Sundays back. Not like I want a faster integration solution. I mean, that's nice, but like, no, I want my Sundays back.

KK Anderson (06:33)

Right.

Mark Petruzzi (06:41)

And Doug, the way you just said that is great because some people would answer your question is, well, people want solutions. But no, I mean, that's a solution. You're giving them a solution, but it's the net effect of that solution on you and to your life and your response. Excellent. Let's, and your organization.

Doug Landis (06:58)

Yep. your organization and like your team and like the

things that yeah, the things that you care about. Like this is how, this is how they're making decisions. It's the story that they're crafting in their head. And it's, what, by the way, like we've all done this, right? We've had to buy solutions. I was a box and I'm like spending a million dollars on the solution. And I'm like, I gotta go sell this internally. I tell you what, I'm to go create a story and I'm going to, I'm going to paint this picture and I'm going to create that story.

Mark Petruzzi (07:04)

Yeah. Yeah.

Doug Landis (07:24)

that can connect everybody so that we can all be aligned. Because it's way easier than be like, here's everything it does. People will be like, okay, great, why does that matter to me? It doesn't matter to me. The one thing on list matters to me. But guess what? I build a story to tell, and it's a lot easier for me to tell. I can get way more alignment and buy-in.

Mark Petruzzi (07:43)

Yeah, you just defined it there. Okay, let us move to topic three, outside-in strategy and one-shot selling, the world we live in today. So most AI sales tools organize internal CRM data, right? You've worked in the Salesforce space for many years, I have as well. We look at some of the challenges there. We look at even bigger challenges in dynamics and other products.

And we all know that these CRM systems are just, they don't have a great deal of just accurate data and things to be able to lever as we go forward. So you built something outside in here and what's, if you built in that process, what's broken about an inside out preparation versus an outside in?

Doug Landis (08:30)

I don't think there's anything broken. think it's just short-sighted. here, I'll give a little context to this. So, you know, my co-founder, ⁓ he was brought in to go do these ginormous product stories, build these product stories for Mark at Salesforce. Giant, like, you know, we're going to change the way Marriott interacts with their customers in the next 20 years. okay. How are we going to do that? How Salesforce going to power that? We've to build a narrative from a product perspective.

Well, you what he did and what great sellers do is like, well, okay, what do I need to know and understand about Marriott's customers? What do I need to know and understand about how Marriott does business, how they think about themselves, how they brand themselves, how their competitors think about them. That's all external information that we need to synthesize to get a deep, deep understanding. What does the CEO think about strategically over the next five years, 10 years about the business? The reality is

is most people are using AI technology to build internal sales AI solutions based on Salesforce data, gone calls or zoom info, chorus information, calendars and emails, right? And notes. Cool. To me, that's all kind of lagging indicator data. It's important. I'm not saying it's not important. It is important, but it's only half the picture because that's all usually a lot of stuff about information that's already happened. Right? We've had these meetings, we've had these conversations. They said, no,

They said, yes, like these are the people that we know. That's cool. But then when I'm getting ready to go have a conversation with somebody, I need all that outside in perspective. I need to understand the nuances of an article or a webinar, a podcast that my buyer was on and they said something specifically about what they're really thinking about. You know, it's like, if I just heard that the CIO of an organization said, we are literally on a spending freeze for the next six months,

until we re until we integrate. Let's just take Salesforce as an example. They just bought Informatica, right? We they are a customer of ours. We're working with them. And you know what? Do know how often I get the hold on? We can't actually talk to you right now because we're so deeply ingrained in this Informatica integration from a people from a process from a product perspective that like we're a little distracted. Like, okay, cool. Guess what? I'm not going to bother any of the MuleSoft folks. I'm actually going to go work with Salesforce core.

If I didn't know that I keep bugging them and they're gonna be like, dude, leave me alone. So the outside in perspective gives you information and insights that most of us miss. And partially because it took us, used to take a tremendous amount of time to aggregate all that information, to contextualize it and synthesize it around the opportunity that you have. But now you can do it in four minutes.

KK Anderson (11:03)

you know, it's something, it's interesting because you're getting on the phone with your buyers and everything in the CRM is basically about the company, about yourself, your company as a seller, who you're representing. It's all very self-centered, obviously. And as you said, lagging, lagging. And you want to be able to see and use a tool like a StoryPath, which is incredible at doing this, at kind of getting in that outside-in approach.

so that it actually helps you when you're in that customer conversation to approach it from their perspective. I mean, if I had a dollar for every time I've said this, I would be a billionaire. It's like, when you're in a customer conversation, you wanna be sitting on the same side of the table as them. You wanna pretend like your email is kk at you'llsoft.com or whoever it is that you're trying to sell to. Like you're not even, you're not there to educate. You're there to

Doug Landis (11:42)

Amen.

Yeah.

KK Anderson (11:54)

you know, solve a problem, right? And so, you know, thinking, kind of thinking about this, this kind of different paradigm. If I'm a seller and I'm spending so much time reading through the Salesforce history and all of a sudden getting really scared because I know there was a closed last deal in 2024 with a different rep and I had no notes and they didn't log anything and I don't know anything and I'm about to call this person and I'm like, you interested yet? Right.

That's just like what a salesperson's like, you know, all of a sudden all of their self-limiting beliefs are creeping up and their confidence is shattered because they're seeing what's in CRM, right? What is your world like? How is that different when you use a tool that is outside looking in versus inside looking out?

Doug Landis (12:19)

Hahaha

I think there's a couple of different ways to think about it. Like when I'm thinking about an opportunity, I need, what is my strategy to win? Like org chart, who's who, like we know we got a multi-thread, we know there's all these things, what's my strategy to win? What are the thread lines, what are the through lines that I can pull on that are connected to us that actually can help us orient around our differentiation? So.

I need to think strategically. So I need a strategist. I need an analyst to help me analyze all this information and show me the things that matter the most. Show me the things that matter the most. And I need it quickly. Because if I'm jumping from meeting to meeting, I got to get booted rather quickly, right? Oftentimes, it's like, you know, it's six or seven o'clock at night, I look at my calendar tomorrow, my ⁓ I have a call at 8am. I am so not ready for that. Right? And so like, cool, what how do I

what's most important for me to get out of this conversation? I want them to say, great, this sounds interesting. I want to learn more. I want them to say, I want to have another conversation. Great. Well, then how do I prepare for that? Think strategically about the plan for the account. I think analytically about where are the opportunities, where are the threads that I want to connect. And then I start to of craft my narrative for the conversation. All that information is external insights, external signaling.

that I want to, that I want to tap into so that I can pull into the conversation and sound credible. Sound like I understand what they're trying to put myself on the other side of the table sitting next to them is ultimately what I'm trying to do. Right. And that's what outside in information really does. My perspective.

KK Anderson (14:01)

And so instead of spending 80 % of your time researching what's in CRM, what would you say? Do your 20 % to know what's there, what the history is, and then 80 % to swap it? Yep.

Doug Landis (14:10)

Yeah, totally.

Great. Yeah. mean, the 20, the, the stuff in CRM, you know, it's, know, it's, just even think about this because we ingest all this information and we look at a gong call. It's like 90 % of it's trash. There's 10 % of that conversation. It's really valuable. It's like, they said these things. Cool. That's what I want. Right. I learned these little thing nuggets. That's what I want. Everything else, the commerce, all those other

orientation of the conversation, this question. It's like, all right, that's interesting. That's why CRM data is helpful. It's like, what have we already tried? Who have we already talked to? But to be honest, a real true enterprise seller is gonna go, cool, I'm not even gonna look at what's already happened. I'm gonna put myself in their shoes and try and think about what are they trying to accomplish? What's getting in their way? What is that gonna do for them if they accomplish this?

who else is involved in this, I'm gonna put myself in their business first. And then I'll go back into CRM and be like, hey, have we done some of this? Or do we have a way in, right?

KK Anderson (15:06)

Doug, I have met my soulmate in selling.

Doug Landis (15:08)

You

Mark Petruzzi (15:08)

Hahaha

KK Anderson (15:09)

I like I have met

my soulmate in selling. just so thrilled to know you. Okay. I'm going to take us to the last topic, because this is the fastest hour that has gone by. know our listeners will do it in two parts, but before we get to the rapid fire, which is everybody's favorite, I do want to at least cover a little bit of this leadership in the AI era, sales leadership in the AI era, because know, boards...

Doug Landis (15:13)

Mmm.

Ha

KK Anderson (15:32)

are gonna fund what they can measure. so we know that story sell, that trust sells, that we have to go through this process of why change, why you, why now. What are two or three ways or indicators, I guess, leaders can do to go to their boards and say, trust-driven selling is working.

We need to try this. Like how, what's the proof? What's the proof story?

Doug Landis (15:58)

Yeah.

I mean, so this investor that I was talking to this morning, we were talking about this, you know, like if sellers really truly develop that level of trust with their buyers, that they truly understand how to become a trusted advisor, which is ultimately what kind of what we're talking about here. And the simple fact that buyers are already 80 % through the buying process or 90 % through the buying process. Guess what that means? We can close deals faster. We can close deals.

KK Anderson (16:19)

Hmm, there's a good leading indicator.

Doug Landis (16:22)

We can close deals faster. And he literally said, he's like, I have our portfolio companies are there, especially smaller deals, man. They're getting done in 24 hours. Like, boom, not two weeks, 24 hours. I closed a deal a week ago in 24 hours. It's like, that was easy. Great. Let's do more of those. ⁓ big deals. I think we can accelerate the conversion rates, the conversion rates across whatever stages you have, because again,

If the buyer's already done this invisible evaluation and it didn't take them nine weeks to do it, they did it in two days. So like, cool. We now can move a lot faster. So I think speed of closing, speed of conversions important. I also think to be honest, if you are truly showing up and speaking your buyer's language and understand their ontology, guess what? Deals are going to be bigger.

KK Anderson (16:56)

Mm-hmm.

Doug Landis (17:05)

It doesn't come down to feature function. We're not like, I'm not just comparing two features and it just becomes a price war. It's like, no, we have a real strategic relationship here because I get you and I know what you're trying to do over the next five to 10 years. And we're in this together. I mean, I was talking to a president to a week ago and he's like, Hey, talk to me about your pricing. This is a true conversation. Talk to me about your pricing. I don't, I'm not negotiating, but I'm just going to get a sense. Cause I'm going to meet with the CEO next week. And I was like, cool. Here's the deal. I don't negotiate.

price is the price. mean, unless you want to do a three year deal cash upfront, then we can talk about it. But guess what? I set the price to where it's a non issue. And he's like, we'll explain that. And I did and he's like, Okay, that makes sense. So this is

KK Anderson (17:43)

I remember the reaction I heard when you

first told me your price. I was like, what? That's it?

Doug Landis (17:47)

And it's just like, here's the deal. don't want this to be, I want a long-term relationship. want, like, I understand the value that we're delivering and are we leaving money on the table? Probably. there potential upgrades in the future? Absolutely. But I don't, it's not about price. It's about delivering value.

KK Anderson (17:53)

Mm-hmm.

Love it.

You're so good, Doug.

Mark Petruzzi (18:03)

let's to our last here that both KK and I love, and that's our rapid fire segment. First question for you, first thing you ever sold.

Doug Landis (18:04)

What?

You

newspapers. I think I was like 10 years old, selling door to door. I'm like, Hey, I'm selling the Palo Alto Times and they and you already get the San Francisco Chronicle, but you want the Palo Alto Times because it's local.

KK Anderson (18:22)

⁓

so good.

Mark Petruzzi (18:23)

And see now that's beautiful. You had differentiation even then in your product.

Doug Landis (18:24)

Hahaha

Yeah.

KK Anderson (18:29)

Okay, a storyteller that you admire.

Doug Landis (18:31)

⁓ Simon Sinek starts, starts with why, like I just, stories live in the why, right?

KK Anderson (18:33)

Yes.

Mark Petruzzi (18:37)

For sure.

Okay, one practice every sales leader should adopt this quarter.

Doug Landis (18:43)

start asking your sellers for the story of the deal. What's the story of the deal? Start practicing storytelling more frequently, like have create story time in your team meetings where somebody steps up and they tell a story. And then you go through the exercise of, that really a story? Was that just a sequence of events? Because the more you, you infuse story into your culture, the more it becomes easier to actually communicate and share stories with your customers.

KK Anderson (19:08)

Boom. Okay, my favorite advice that you would give to your 21 year old self.

Doug Landis (19:13)

This is a doozy, because on the one hand, I'm kind of like, just keep doing what you're doing. Life is great. On the other hand, it's like, you can work on the people pleasing a little earlier in life, because that doesn't necessarily get you what you think it's going to get you.

Mark Petruzzi (19:29)

Interesting. Okay, last one, your favorite non-business book.

Doug Landis (19:32)

Michael Singer's The Surrender Experiment. It's incredible story. Have you read it?

Mark Petruzzi (19:35)

read that one. Wow.

I have not, no, but I will.

Doug Landis (19:38)

It's so good.

It's actually so it's really cool. It's what anybody that's in business should read it because it's really all about like, look, there's only so much we can control in our life. Right. So you have like a hippie living in his van in Florida, ⁓ who's a total yogi becomes the CEO of a multi-billion dollar publicly traded software company. And he talks about his entire journey and how he continued to surrender to kind of the flow of life, even in some of the most challenging times. It's a great book.

KK Anderson (20:05)

Okay, well, we'll definitely put the

link to that in the show notes. I'm gonna get that one for sure. Okay, Doug, this has been so much fun. So much fun. Thank you. I can just say thank you on behalf of our audience. You just did a great job. I appreciate it. Mark, you're awesome as always.

Doug Landis (20:15)

Thank you. It's been great.

Thank you.

Mark Petruzzi (20:23)

Thank you. Thank you. What a great show. So thank you all. Appreciate it again, Doug, and all the best.

Doug Landis (20:25)

Cool.

KK Anderson (20:30)

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, Mark Petruzzi and KK Anderson sit down with Doug Landis, Co-Founder of StoryPath.ai and host of Sales Stories, to unpack how AI is reshaping the buyer seller relationship and why most sales teams are still playing by outdated rules.

Doug shares why AI has enhanced the buyer’s world more than the seller’s, what he calls the invisible evaluation, and how today’s buyers are 80 to 90 percent through their decision process before ever speaking to a rep.

The conversation dives deep into the crisis of sameness in modern sales, why traditional discovery no longer works, and how trust and story have become the last true differentiators in a crowded market.

If you are leading a sales team, building a pipeline, or navigating complex enterprise deals, this episode will challenge how you think about first meetings, process, and positioning in an AI driven world.

What You’ll Learn:

• AI and the Buyer Shift: Why 89 percent of B2B buyers are using generative AI and how 83 percent of the journey now happens without a seller.
• The Invisible Evaluation: How buyers are researching, comparing, and shortlisting vendors without leaving digital breadcrumbs.
• The Crisis of Sameness: Why AI tools are causing sellers to sound identical and how that kills differentiation.
• First Meeting Reimagined: How to show up with a hypothesis, point of view, and buyer language instead of running outdated discovery scripts.
• Trust and Story as Strategy: Why storytelling is not case studies and how narrative builds alignment across large buying committees.
• CEO of the Territory: Why modern reps must think like business leaders, not process followers.

Key Topics:

• AI’s impact on B2B buying behavior
• Rethinking the traditional sales process
• Discovery versus hypothesis led selling
• Building trust through empathy and buyer ontology
• Story as a tool for alignment and influence
• Coaching sales teams in a new paradigm
• Differentiation in enterprise SaaS and AI markets

Guest Spotlight: Doug Landis

Doug Landis is Co-Founder of StoryPath.ai, an AI native guided selling and storytelling platform designed to help sellers show up with differentiated perspectives, not just better automation. He previously led global sales productivity at Salesforce, served as Chief Storyteller at Box, and was a growth partner at Emergence Capital.

Doug is also the host of Sales Stories and a long time advocate for trust based, story driven enterprise selling.

🎧 Listen now and follow Selling the Cloud for more insights on modern go to market strategy, enterprise sales, and how to win in a one shot world.

Mark Petruzzi (00:34)

Welcome to Selling the Cloud. Our guest today is Doug Landis. We're very fortunate to have Doug, who is the co-founder of StoryPath.ai, host of the Sales Stories podcast. He's a storyteller and he's just successfully built early stage companies time and time again. Doug has led global sales productivity at Salesforce.

He served as the chief storyteller at Box and spent seven years as a growth partner at Emergence Capital, helping SaaS companies scale smarter. He has sold everything from newspapers and ice cream to enterprise databases and cloud software. Today, he's really focused on and really enjoying building up StoryPath.ai.

StoryPath is an AI native guided selling and storytelling platform that helps sellers show up with differentiated perspective, not just better automation. Three topics we'll cover today. How AI has changed buying behavior more than selling behavior. Why trust and story are the only real differentiators left. And how sellers can compare differently and win in a one shot world.

Doug, we're so fortunate, as I said, to have you here, and welcome to Selling the Cloud.

Doug Landis (01:50)

Thank you. So great to be back. That was all I think I was on a long time ago. I don't even remember what we were talking about back then. And you know, it's interesting as you were doing the, you're going through the intro, I was thinking, I was like, well, given the fact that it feels like everything's shifting to be AI native AI first, everything's all AI. Just does the podcast shift to like selling AI instead of selling the cloud?

Mark Petruzzi (01:53)

Be back.

Doug Landis (02:14)

By the way, not yet. Just for a little side note, was on a webinar with about 250 operational leaders, sales and rev ops leaders. And I asked the question, Mike, what percentage on average of your entire go-to-market tech stack is still pure SaaS versus AI? And the answer was at least 85 % of their stack was still pure SaaS. So while we say everything is moving AI and it's moving fast, really fast.

There's still so much that's already like fully baked in. so now everyone's been trying to figure out like, how do we actually, make it additive instead of completely rip and replace. But anyway, so the pod selling the cloud is still relevant for awhile.

Mark Petruzzi (02:52)

Yes and no, we're actually working on exactly that now, Doug. So you're hitting us right at the...

KK Anderson (02:56)

Your ears must have been burning, Dad, because we've been talking about a

Doug Landis (02:57)

really?

sit in a space all the time like, hmm.

Mark Petruzzi (03:01)

No, no,

you do, you actually put out these ideas without even saying it. Because I actually came up with this idea last night and shared it with KK. So I was waiting. you know, we'll talk more about that, Doug. And so maybe you influenced me without even knowing it. But there are things that are changing. There are things that we want to make sure our audience is changing with it.

Doug Landis (03:10)

No way, that's amazing.

Mark Petruzzi (03:25)

And it's just really, it's incredible to have you here and you keep getting smarter than even the last time we had you here. So we love it. a couple times you've said something that really stuck with us through your writing, through your podcast. It's all blurred to me because I've listened to all of it over time now.

but that AI has enhanced the buyer's world more than the seller's. What do most sales teams misunderstand about what's happening right now? And how can they change their approaches and their processes to be able to really make sure that we are clicking and fitting with the new buyer's world that is out there?

Doug Landis (04:06)

Hmm.

Such a great conversation to have. I love this. You know, when AI first hit the scene, I think everybody asked like, okay, what does this mean to me? What is this? How can I use this? And I think what the reality is for buyers and sellers, AI has dramatically changed how they engage with each other. The relationship between buyers and sellers is changing pretty dramatically. If you think about it for buyers, know, AI has actually become a real superpower for them.

You know, they can aggregate data, they can run analysis, they can do things so much faster than ever before. They're just leveling up overnight. And so I'll share some statistics with you. think that are really, really important to understand how what's changing and shifting in this relationship. If you think about this, LLM traffic is projected to overtake traditional search by the end of 2026. So what that means is more than 50 % of your buyers are going straight to a chat bot to begin their buying journey.

So think about that and why is that? And the reality is this as agents have gotten better, you know, it's really interesting is what they can do in minutes or hours is what it used to take buyers weeks and months. So the buying process used to be months long and now they can actually go through it in hours because what an agent is doing is an agent will actually look at their, they will form preferences.

And they're going to do it in a way that like humans do. But what's crazy is the amount of information they can, they can analyze is stuff that buyers would normally think about over time. Things like, I don't know, think about the data points of like user reviews, right? Or community sentiment or tech, technical documentation or support quality or integration pricing, all of that. And agent can analyze all that in seconds. And a buyer would normally take, you know, weeks or months to go through that. So if you think about it,

Statistically speaking, what is it? 89 % of B2B buyers are using gen AI in their purchasing process. The crazy thing is 83 % of the buyer's journey happens without a seller. So that means if a seller is only involved in 17 % of the buyer's activities, then sellers need to show up a little differently. They need to understand and almost anticipate the fact that the buyers are going through a buying process without them.

We call this the invisible evaluation. They're evaluating solutions and they're evaluating ways to think about solving problems without any of us knowing. So if you think about like, we've all bought software, right? And so we normally would think about buying software, like maybe we'll go to a webinar, we'll go to a website, we'll talk to some people, we'll reach out to an SDR, we'll download a white paper. That is leaving signal. That's leaving breadcrumbs all over the internet. And solutions out there could pick up on that and be like, ⁓ hey,

Doug is out exploring something to solve for forecasting. Awesome. I can reach out to him. can do some, you I can do some outbound now all that's happening in a chat bot and there are no more breadcrumbs. And so like how do sellers know how to marketers know how to brands know that their buyers are actually out there in market. It's really, really difficult. The problem is sellers show up.

And I fundamentally think this is going to change the entire sales process. When you think about sales process, what do we think about the traditional sales process? We're going to take a buyer through like, you know, all these stages, discovery demo, you know, negotiation, more discovery, multi-threading, all of that buyer. like, no, I have two questions. I've whittled this down to three vendors. And when sellers try and go backwards, it's like, as a buyer, I'm, losing my mind.

Mark Petruzzi (07:20)

Doug, you, wow, would. And I'll tell you, I'd love to share a couple thoughts on that, that maybe can even, you know, maybe escalate us even a little more in some of this analysis. So I have been personally on a journey for about seven years where I have been telling all my clients, anyone who reads anything I put out that, you know,

It's a different process. was a different process seven years ago even. At least that's when I figured out. Probably was five years before that. But with all the tools that were out there, buyers wanted to buy differently. And I was amazed that some of the best sales reps that I've ever worked with were not responding to that. Some of them were, and I've been able to turn teams of sales reps into

into really understanding the buyer journey and understanding that the seller journey means nothing in all And I'm so proud of what I've done with some clients, but I've seen some clients just not wanna go there. They just won't. That was seven years ago. Now you compound all this with AI and what you just described so articulately, there is like, it's all.

whole new game. Like we almost have to get these sales leaders like bats that they can run around sort of hitting sales reps a little bit on the head and saying like, you have to believe now. It's so different. It's not even there's no resemblance. So it's incredible. But I love how you set that up. And I'd love to go deeper into what do we do with with that? And how do we get

Doug Landis (08:44)

Hahaha.

KK Anderson (08:50)

So.

Mark Petruzzi (08:58)

the most stubborn sales reps to understand that we're in a new paradigm.

KK Anderson (09:03)

Well, and Doug, before you answer that, let me just add on. let me add onto that. So the buyer motion has changed, but we still have to go, we still have to take them through the process of what I call running the bases, like in baseball, right? And you still have to go through this whole idea of what we call the two-cell.

Doug Landis (09:05)

Great question.

Mark Petruzzi (09:05)

It's

okay.

KK Anderson (09:23)

process, is like our sale is getting that buyer to articulate why they need to change. What is the problem they need to fix? And the second sale is why you and why now? And so if they're, when they're coming to you, and this I know is where something like Story Path is so incredibly powerful. We've seen it firsthand with our clients, but if you're getting to that first conversation and that buyer is like, dude, I already know this. I don't want to hear this, right?

Like what are, what's your advice to the sales leaders out there who are working on this with their sales team? They still have to close that first sale. They still have to like make that psychological invisible sale happen. Talk me through like, what does all this mean?

Doug Landis (10:00)

Well, look, I mean, why change? Why now? Why us or why change? Why us? Why now? The whatever flow you use is still relevant, 100 % relevant. The difference is sellers need to show up anticipating the fact that buyers have already been thinking about this. And so instead of going through the traditional discovery questions, which is, you know, kind of a Spanish inquisition of stupid questions, it's like, I need to like, let's just call a timeout. My hunch is you've already analyzed

You've already deeply understand the problem you're trying to solve. You've already analyzed all the different options out there. You've done all the analysis if you're a modern buyer like most of the buyers that I'm speaking to. So the first question is, since you've already done that, you probably have a pretty good idea why changing right now, why changing from what you're currently doing might make sense. I have a hypothesis about it. I'd love to share that with you, but I'm curious as to as if you've actually gotten to that point already.

KK Anderson (10:51)

So the upfront contract, the way you set it up.

Doug Landis (10:52)

Interesting, right? It's like

Right. It's all, it's all how you set it up. It's like, if I anticipate the fact that they've already done this and they've got a pretty good understanding as to why change might make sense. Awesome. Let's have that discussion. I've got a perspective about it because I talked to other people just like you all the time. And I'd be happy to share that. ⁓ but I also want to know if you're, if you've already done the analysis and you're already there because most of the buyers I talked to you already have. Right. So

It's almost like, it's almost like kind of making an assumption. I'm not going to tell them that they've already done this, but I'm going to kind of, it's a little bit of assumption that's like, you know, if this is a big enough problem here and a hair on hair on problem that we continue to see, then my hunch is you've already done some around it.

KK Anderson (11:32)

Talk us through,

I've heard you say this multiple times now, what you call the crisis of sameness.

Doug Landis (11:37)

Well, so unfortunately, the crisis is so on the seller side, we all thought like, AI is going to make us so much more productive, we're going to become superhuman sellers, right. And the reality is, sellers are all using the same, you know, custom GPT that they built, they're all using chat, GPT or gems, they're all using kind of their own internal data. And they're showing up with the same messaging, the same pitch, the same everything because they don't under

because they haven't stopped and said, wait a minute, if my buyer's 80 % of the way through the buying process, if they already have a pretty good idea of why change, why changing might make sense and why it might make sense now versus waiting and what are kind of my best options. And if I take them through a standard pitch or use the same email kind of framing that everybody else is using, then I sound like just like everybody else. There's no differentiation. And I think that's one of the challenges. I literally was talking to an investor right before this call.

And I was sharing this with him because this is kind of a part of our core thesis is as an organization is we've to get people away sellers away from sounding just like everybody else. And he was like, I literally have gotten 11 of the same emails in the last 24 hours. It's they look in, they look and feel the same. And so it's like, okay, if we're, if we're all kind of following the same playbook and we're using the same tooling,

then how do we really start to differentiate? And I think the first thing is you got to first understand where your buyers are now. That's the very first step. The second for a seller to get out of this crisis of sameness is you got to start thinking about being different, you know, and we have a whole thesis on that. That's through trust and story.

Mark Petruzzi (13:04)

and you know what Doug and KK, I'm gonna ⁓ kind of bust this out, I think, to a whole level here with some of these thoughts. So, and this is why KK and I are so good together and why we're so impactful for our clients because we have these debates all the time. So I'm gonna bring one of our debates to this podcast. KK just described the four bases, like you've gotta go around the four bases and she's incredible.

from a process standpoint, sales competency perspective, and I totally get the perspective. I kind of think it's gone to a different point here. And when I show up to a sales process, I kind of think of like I'm showing up to play baseball with the Savannah Bananas, that group that does all that goofy, crazy stuff, right?

Doug Landis (13:51)

Love that.

Mark Petruzzi (13:51)

So what I have to do is I first have to understand what are the rules today, like real quickly, not deep, but what are the rules that we're gonna go to to play this game? Let me do my research, let me learn how they played every other game they've ever had. Let me come in with that. And then I wanna see, are we even using bases? Or are we just hitting home runs and catching balls behind their back, whatever they do.

Doug Landis (14:15)

Ha

Mark Petruzzi (14:16)

So I think that's where we are here as well. And that's why I also feel like the concept of the sales rep being a CEO of their territory is real again. And we all watched over 10 years, 12 years, the last 10 years, 12 years, all the technology that sales leaders were putting in place.

Doug Landis (14:30)

Yeah.

Mark Petruzzi (14:39)

They then started to say, well, we don't really need people that could be the CEO of their territory. We're going to give them great process and great technology. And hey, it works. Worked. They were growing, especially in SaaS companies, super fast during this time. So I don't argue with the success. But before that, and I think now again, you need at least a subset of your sales team to have that level of intellect and curiosity.

and really figure those things out. So I'll weave that together if you don't mind with a question, a more specific question. So if we think buyers are now 80, 90 % through their decision process before they even talk to a seller, how should it change how the rep shows up in a first meeting? And my hypothesis here is that a good one, right? Like you almost have to go in and figure out what game

not to call this a game, but what are the rules of this process before you even jump in? And you gotta be smart enough to be able to figure that out, which also comes down to the talent management, making sure you have the right people and the right roles.

Doug Landis (15:35)

Yeah.

Yep. it's interesting, you know, it's, would, I would argue what a seller needs to do in the first meeting and first conversation today is arguably the same that I've been touting for years, which is show up with a point of view, show up with a hypothesis, anticipate, try and anticipate where you think they might be might by the way, is a very important word because I'm a linguist at heart because you can't tell somebody where they are. If you come in and tell the buyer where they are, to be like,

GFY, you don't know me. ⁓ think, wait, here's, I wanna actually address that, by the way, I love the of the metaphor of the Savannah banana baseball team versus traditional baseball in terms of the shift that's happening. I believe there's two parts actually going on. There's the operational piece of selling which still exists. We still need to understand where does procurement fit in this process.

KK Anderson (16:19)

Yeah.

Doug Landis (16:31)

What about security? What about legal review? We'd like, those are operational things that we need to do to get the deal done. Correct, right? We still need to do that. Also, people likely still need to see some sort of demo. They need to understand how this might look and feel and fit in their environment, right? They may conceptually understand the problem they're trying to solve and the options, but you know, they can do all that through these chatbots, but they also then need to look and feel and think more deeply about the integration and how the data flow and then...

What kind of risks is this gonna create? So like there's, me, that's kind of the operational stuff of the process. And that's where I agree with KK and that like, there are still bases that we still have to, you know, touch, right, to get a deal done. However, I'm gonna put on my Savannah banana outfit and go like, the way I get to those bases might be a little different,

I might, by the way, run to second and then go to third and then to first and then to home. I might go like high five the pitcher, right? Right? So, but here's the key. The key is in order for me to leave home, the home base in order to go to any base that makes the most sense. I have to show up with a perspective and a point of view and an understanding of where my buyer is. And I have to speak their language. I have to understand their ontology. I have to understand

Mark Petruzzi (17:20)

There you go. Yep.

Doug Landis (17:42)

you know, who they sell to and what they're trying to accomplish with their customers. And that's the language that I need to speak. And if I just show up and I'm speaking my language and I'm asking my discovery questions and I'm putting all the pressure on the buyer to go answer my questions as a buyer, I don't want that interaction anymore. And guess what? I shouldn't have to have it. I shouldn't have to have it. Right. So, and so like,

KK Anderson (18:03)

Totally appreciate that

Doug Landis (18:06)

I'm going to go into the conversation and say, like, let's just say, Mark, I'm trying to sell to you. I'd say, like, Mark, I have a hunch. My hunch is you're so sophisticated that you've already done an insane amount of analysis about the problems that you're currently trying to solve. Just a hunch. And that you've already kind of whittled this down, your selection down to maybe one, two, three different potential partners to work with. My hunch is you also have very specific questions that you haven't really wrapped your arms around yet.

And the reality is those questions, that's kind of where I want to spend our time.

Mark Petruzzi (18:35)

And right after I gave you a big giant hug and said, wow, you get me, Doug, would then be like, yes, and Doug, here's what I need. I need to get X, Y, and Z done. And if we get those things done in a positive way, you got my business. And we're gonna do it really fast because you get me already, Doug. that.

Doug Landis (18:35)

How does that sound?

Yeah. That's, mean, and, and, and, so this is, this is the new reality, right? And I think the challenge is both at a leadership level is we got to quit forcing reps to follow this process. And we also at the leadership level, we need to coach our reps to be able to show up with a really, really strong point of view and an understanding of how to speak our, our buyer's language and understand their ontology. The challenge is if I'm a rep and I have a territory and like, I'm the CEO of my territory, but my territory has like,

50 different verticals, different kind of companies and different industries, I got a context switch and that's really hard. Instantly, I've got a series of meetings, I've got calls back to back because my BDR is crushing it and setting up meetings, which we know is really hard. But now I'm going from talking to somebody on oil and gas to manufacturing to retail. I'm like, ⁓ how do I do that? And so what's easier for me is to let me just go through my playbook, follow, ask my questions.

KK Anderson (19:28)

Mm-hmm.

Doug Landis (19:47)

do some validation, talk a little bit about us. ⁓ Unfortunately, it happens way too early. And then the buyer's like, all right, well, you sound just like everybody else. Cool.

KK Anderson (19:58)

Yep. So true. You, I you are articulating this so well. Really. It's incredible. the value hypothesis is critical and you know, well, I don't want, we, don't want to go too far into Story Path, but the very first time I logged into Story Path, the first question it asked me was, what is your value hypothesis? Who are you? What percent are you selling to? What challenge are they trying to solve? And why are they trying to solve it?

Doug Landis (20:00)

It's hard

Thank you.

KK Anderson (20:20)

right, so that you can know exactly kind of what your POV is. So let's move on to the second topic here about trust and story and how they help us win the deal. And so in this kind of world of sameness where we're flipping between industries and on back-to-back calls and we all sound the same, right, a lot of times we're reciting the same case studies, the same stories, and sometimes

Like sometimes a salesperson will literally feel like a broken record because they say the same thing 100 times, right? And so, you you and I both know that that story is not just case studies. ⁓ Most case studies aren't even real stories. Like, let's be, let's be real, right? They've taken on a life of their own over time. And so, you know, talk to me about, about what it is.

Tell me about why story is so important and how that helps build trust.

in the first

Doug Landis (21:10)

Well, I mean, look, here's the thing. think, well, there's two parts to this, right? So again, our core thesis is to really truly differentiate as a seller today. It's all about trust and story. Trust is understanding your buyer in a really, really deep way. I was about to use intimate, but that's weird. But like truly understanding your buyer,

Mark Petruzzi (21:27)

You

Doug Landis (21:29)

having, putting yourself in their shoes, having the assumption that like, you know, Mark's already 80 % through the process. He's done the analysis. I understand your language and ontology. That's all going to build trust, right? And I can take that from the company level all the way down to the individual level. And we'll talk a little bit more about that. When I'm sharing back, when I'm communicating back with Mark as my buyer, I want to communicate back in a way that is easy for him to understand, a way that demonstrates some level of empathy, connection, right? And

easy for him to internalize and turn around and go share with others. Because Mark is one of 17 people. If the deal is over $250,000, thanks to my friend Jen Allen, she just posted a whole bunch of stats. If a deal is over $250,000, there's like 17 buyers now involved in the process, or on the buying team. That's crazy. So guess what? Mark has to go talk to 16 other people and try and build alignment. Like is this a problem that is worth solving? Can we get everybody on the same page?

If I just go, here's all the facts and stats about our product, here's what we do, here's how we do it, here's our case studies, Mark has to internalize all that and be like, all right, I'm gonna do the best I can to try and share this. However, what if you were to flip this? What if you were to reframe the way in which you orient the conversation and share a level of, here's what I think I understand and then.

and weave that into a narrative, into a story that is a very short, very crisp, easy to digest for Mark, then guess what? I'm earning the next conversation. I'm earning a deeper relationship. I'm building that connection with empathy because story is how we naturally communicate. We can use facts and stats and data to back up the story.

But when we just lead with all these statements, it's really difficult for us as listeners, as human beings to remember that. I mean, just think about school, multiple choice questions. At the end of a test, if you were to ask me like, do you remember that question? I'd be like, nope, blacked out. All right, the essays I remember.

KK Anderson (23:23)

So,

love what you're saying, Doug, and I couldn't agree more. And where my head is going is are things like you're telling a day in the life story or a future state story or here's where you are now. Tell me a little bit more about when you're

Doug Landis (23:35)

Totally.

Bunch of different types. There's a bunch of different story types that you can actually tell. Yeah. Current state to future state. Look, at the end of the day, a story is really about from two. You're taking, you're trying to help somebody imagine going on a journey from somewhere to somewhere else. Right. It's either I'm taking from first base to second base or from first to third. I don't know. Right. So like, and so you can tell that from, from the experience of another customer that was similar and the journey that they went on.

KK Anderson (23:50)

first face to say and juggling balls behind your back.

Doug Landis (24:03)

You can tell that from the standpoint of like, hey, by the way, it could just also be like a, hey, Mark, we're just starting to get to know each other and starting to unpack like the connective tissue of this problem that we think might actually be bigger. So let's, let's, let's talk about the next conversation and talk about the story, about the flow of our, of our ongoing conversations. Cause I know there are 16 other people involved in this and how that might look and feel. There are a number of different stories that we can tell. Oftentimes telling a customer story is a really great way to demonstrate some level of credibility.

The problem is, sorry marketers, I love you. Stop following the old school frameworks. Problem, solution, ROI. No characters, companies aren't characters. I don't know how to go tell that story, so what do I do? I say, well, yeah, know, Mark, this reminds me of conversation I was having with Cisco. They're like, okay, how is that even relevant? They're not even like, it's like apples and tree bark.

Mark Petruzzi (24:36)

Mm-hmm.

Doug Landis (24:56)

doesn't even connect. You know, it's like, oh, okay. And then I'm trying to draw some connected tissue, because that's the only story I remember. And again, take that territory where I've got 100 different industries. How do I remember stories, customer stories for every single industry? And so it's like, so there's a bunch of different stories you can tell, right? So how about tell your own personal story? Right? Your own personal aha story, because you understand if I understand Mark's world really well, I'd like, you know what, here was my experience.

KK Anderson (25:00)

Right.

for the opportunity to ask questions.

Doug Landis (25:21)

You know, I've, I understand your problem that you're experiencing because I've actually had something similar. So maybe it's a personal story. Maybe it's a, you know, maybe there's a, you know, a why so, many stories live in the why not the what or the how. Right. So like, why did we decide to go? So, so for example, why did we, why as an organization, did we decide to tackle this particular problem? Why have we made it our mission to help people solve for this particular problem?

KK Anderson (25:35)

What do you mean by?

Doug Landis (25:46)

Why, why did I decide to come work for this company? I decided to come work for this company. started, decided to start Story Path because I fundamentally want to change the world of enterprise sales, period. Right? So like, guess what? I know Mark loves enterprise sales. He and I are aligned because this is what we both want to do. So like, I just told my own personal why story or I could tell my personal why story. And it's like, all of a sudden now we're building connection.

Right? So there's, it's just a lot of different stories that we can tell in every conversation. I think there's a couple of things. One, we're not thoughtful enough to just take a minute and be like, what stories do I actually want to tell in this upcoming conversation? Just take a minute. Just think about that. How do I want to incorporate those stories in the conversation? Which one should I be ready, ready for? The problem is, is a lot of people just don't understand actually how to tell stories. and we haven't really helped them. Well, we are now as a company.

I mean, at the end of the day, Story Path is the story company.

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 conversation on Selling the Cloud, Glenn Poulos dives deep into what it really takes to scale a distribution business from startup to successful exit. From growing Gap Wireless from 1 million dollars in revenue to 84 million over 15 years, Glenn shares the strategic decisions, mindset shifts, and leadership disciplines that enabled sustainable growth in the telecom technology sector.

Glenn unpacks the importance of franchise vendor relationships, why brand positioning determines sales velocity, and how to structure an organization with the right people in the right seats. He also tackles one of the most critical dynamics in distribution: building trust with manufacturers while managing the real risk of going direct.

The episode closes with a practical and grounded perspective on AI in sales. Glenn explains how to use AI as a powerful assistant across departments without sacrificing the human connection that ultimately closes enterprise deals. Plus, stay for the rapid fire segment where he shares hard lessons from selling his first company, advice for his 21 year old self, and the sales habits he still practices today.

What You’ll Learn:

• Scaling from Startup to Exit: The key inflection points that helped grow Gap Wireless from 1 million to 84 million in revenue.
• Brand Strategy in Distribution: Why representing top tier brands is essential for competitive sales positioning.
• Right People, Right Seats: How organizational structure and disciplined hiring drive long term growth.
• Manufacturer Trust Dynamics: Navigating co-selling, exclusivity, and the risk of vendors going direct.
• AI as an Assistant, Not a Replacement: How to use AI for research, prep, legal review, and financial insights without losing the human edge.
• Sales Discipline That Compounds: Daily habits that create visibility, opportunity, and long term career growth.

Key Topics:

• Franchise distribution models in telecom and technology
• Relationship first selling in enterprise B2B
• Organizational design and leadership evolution
• Managing vendor partnerships and channel conflict
• AI in sales operations, finance, marketing, and legal
• Career defining mistakes and lessons learned

Guest Spotlight: Glenn Poulos

Glenn Poulos is a sales expert, author, and serial entrepreneur with over 40 years of experience in complex B2B selling. He co-founded Gap Wireless and scaled it into a multi million dollar distribution company before its acquisition. Today, Glenn leads ProgUSA and is widely recognized for his thought leadership on sales growth, leadership, and the practical application of AI in business.

🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping the future of enterprise sales.

Mark (00:31)

So let's move to topic three, scaling a distribution business from startup to exit in the telecom technology sectors, as a whole. So let's talk a little bit about your journey building Gap Wireless. You co-founded it in 2007, hit a million dollars in revenue that first year.

Glenn Poulos (00:33)

Okay.

Sure.

Mark (00:51)

and I believe it was 15 years later, sold to 10 WS. What were the major inflection points or really what were the decisions that enabled you to scale in the way that you scaled?

Glenn Poulos (01:02)

So numerous things. at the end, we were 1 million in the first year when we sold it to NWS and we did 84 million in revenue. So over the 15 year period, we grew from 1 to 84 million. And again, we were a small company, right? So I mean, was, you know, and at the, when we exited, there were 44 people.

Right. So it was pretty good, pretty good growth. Right. So, in a distribution company or in many, I've been into the distribution my whole life. So really can't comment much on any other kind of company because I've never really experienced them. Right. But, it's the first thing is always focusing on the relationships before the transactions. Right. So that no need to really beat that to death.

the people piece is very important. The relationships with the, the customers, the employees and the suppliers is critical, right? when you're a distributor, the key is having the key, the killer brands under your moniker, right? Like you need access, franchise to access.

to the key brands, right? And the kind of world that we were in ⁓ and I've been in is one where it's kind of a, we'll call it monogamy based franchise relationship. Meaning I wasn't, I'm not the Rexel or Ingram Micro that has every brand and I'm a trillion dollar corporation, right? That's not what we are, right? We're a multimillion dollar company. And so, the screws, we would only represent this screw company.

Right. There were other competitors, but our goal and our job was to get a franchise relationship with ABC screw and sell their screws and their screws only no competitive. Right. And so we would build the market for them. We were approached that company. They were maybe in Italy. They make the best screws in Italy. And we'd say we want an exclusive franchise relationship.

with you guys in Canada, the US, North America, Central America, wherever it was we were selling, wherever the territory was available. And so you get that, you wanna build that relationship with the vendor early and that's the most important thing really because you wanna be having the best brands to present to the customers. Then it shifts and the customer becomes the most important, right? But if you, let's say you have the customers but you have the D, E and F brand.

it's game over, right? Like I won't even, I challenge people, sales guys and gals that when they get a job, spend a few months and figure out where you are in the pecking order of the world of your market, right? Are you guys the number three, the number four, the number five, the number two, the number one? If you're below number two, I say quit and get a better job at a better company because you can't, you can't replace today, right? Once today's gone, it's gone. And so if you're trying to promote brands that are well down the stack of

what people want to buy and what have you, you waste too much time selling the company and not enough time selling the solution and the product, right? So you want to have those vendor relationships. and so ⁓ some of the other things about about building the business, you know, is learning how to step back and put the right people in the right seats, right? So ⁓ structure first, people second.

And everything has a process, right? So what do I need in order to be successful? And then do I have the right people in my organization to occupy those seats? And if not, I find the right person and put them in the right seat. I don't say, hey, our finance things are growing. We got more challenges in finance and we've got,

Jack and Sally and you know Sally's been here longer and she's doing a good job and whatever let's give it to Sally. No it's like I need a director of finance now or I need a CFO what are the rules for the CFO? Does Sally or Jack have possessed that? Anyone else in the company? No I have to recruit out of the company.

And I'm sorry, don't, it's nothing personal, right? You got to the right person in the right seat. And so, and that allows the founder to step back a bit and focus on the higher level visionary type functions of the running the company, right? And guiding the direction, knowing that the different, the different roles are well covered, right?

so I'll just take a quick breath and see if there are any specific questions about that or

KK Anderson (04:48)

It's so,

it's fascinating and so interesting. we do a lot of, and I do a lot of work with distribution companies and with manufacturers alike. And so one of the things that comes up a lot is trust, right? Distributors worry about manufacturers going direct. Manufacturers worry about losing control of the customer experience and conversation and getting to talk about their product. So from your perspective as the distributor.

what actually builds that trust with the manufacturers? And is that, from your perspective as well, difficult to be able to trust the manufacturers with your pipeline, with your customer base, going, know, co-selling, if you will?

Glenn Poulos (05:28)

so yeah, that is like the key of it all. Like, I mean, that's really like, that's like a like a masterclass what you're just asking there, right? Like, you can go in so many different directions. But but ⁓ and I hear you so well what you're what you're asking me the the

you have to be a little bit paranoid. You have to be pragmatic, and, sometimes you just have to, you you just have to let it be what it's going to be and accept it and, sometimes move on. Right. In the sense that, the company I'm in now, it's not a huge company. we have 11 franchise relationships. And so I have to balance the needs, wants and concerns of those companies, but some are bigger than others. Yeah. My main brand and what have you. And yeah, I

I if I get them to a certain point, they might go direct, right? So it's a bit of a balanced mediocrity, right? If you grow them to a certain value, it's cheaper for them to open an office in that country and put in direct salespeople. But the thing is, it'll happen, right? And so you always want to be using that brand to leverage new brands coming on board.

in the possibility that you might lose it. Because you can't defend against an inevitability, right? And so I sort of like trust.

KK Anderson (06:36)

to you before

where lost like a manufacturer's gun direct

Glenn Poulos (06:40)

Yeah, so essentially we sort of, unless they're a company that's pure distribution focused, ⁓ where they only sell through distribution, it's just about doing a good job and stuff. But if when it's a difference between going direct and distribution, if they might go direct, then if they hit 5 million, you can, you can basically count your days until they go direct.

because mathematically it's cheaper to go to rec at 5 million. So if you can get them from one to 5 million, you're kind of in the sweet spot making lots of money. They got a lot of ifs and buts about whether they will or won't go to rec, but above that, it starts to get risky, right? In terms of...

like sharing the information and what have you, I believe in, like I call it humble bragging early and, and always. Right. And so I like, for instance, with my guys, they'll, they'll call me and they'll say, Hey, I'm just on the way home from, you know, XYZ. And they're looking at a new, discombobulator 50 grand, like blah, blah, blah. I go, that's amazing. Did you tell the vendor?

Right. And they're like, no, I said, you should have called the vendor and told them. And I said, you got a humble brag, right? and, what I mean by humble bragging is like, you don't want to do it in a, in a way that's like negative in, in any kind of capacity. You want to say, you know, Jack, my God, I just had an amazing call. I just had to share it with you. We're in an XYZ. They're looking at a discombobulator. They might need two of them. It's 50, a hundred K. my God. I might need your help with the demo, And so what's the vendor doing? He's thinking, ⁓

Mark (07:37)

Thank

Glenn Poulos (08:03)

Bob's in at XYZ, Bob's got two discombobulators on the go. That's a hundred grand. I could really use that towards my quota. What can I do to help Bob get the deal? And also what's happens is, that Sally from the competitor who maybe there's two distributors, right, calls and says, I got wind that there's like a week later calls. got wind that XYZ might be looking for some discombobulators. Nope. That's covered by, by Glenn's company or whatever, right? Stay away.

And they, because that's what just manufacturers often do. They divide up the landscape, right? It's like, nope, we've already, we're already working with someone there back off, right? And, and so I believe in being very liberal in my new company here, small as we are, my ERP system, I had custom programming done so all my vendors can log in and look at the funnel and see only their

funnel items, obviously they can't see my other vendors, but, and, they can see most of it, but not all of the records, right? Like the internal chatter box notes they can't see, but there's a more generic note section. can, they can see probabilities, dates, products, who's involved in center, et cetera. Right. and so I'm not sure I directly answered your question, but I mean, Oh, okay.

KK Anderson (09:08)

For good, you absolutely did.

You did, thank you.

Mark (09:11)

Beautiful.

All right, well, let's move to our final topic. you know, this is a popular one or maybe popular is not the right word. It's it's just out there everywhere we look. AI and technology and sales. how do you use tools without losing that human connection that you've shared within your book and within a lot of the work you do online? What's what's great about what you've achieved in the

social media world and the media world. you're a LinkedIn top voice. your focus and a lot of what you do today, you describe yourself as an AI and sales growth expert. But after spending 40 years building relationships, mostly face to face and mostly over the phone, how are you thinking about AI's role in sales with all this new capability we all have?

Glenn Poulos (09:58)

Okay, so my, and of course this is my opinion, right? Obviously. And, and so some people might argue or they touted it for different, there's so many things on social media now about using AI and I'm like, yeah, no, no, I don't think so. But, so I, I think of AI and I want to use AI to remove friction and, not replace the connection. Right. And so I treat it like a strong assistant in every department.

Right? Finance, marketing, operations, sales, legal. And so it can help you with research, with prep, with summaries, with drafts, with ideas. Right. And but not to replace it. Like, for instance, I know I didn't try this, but I mean, we have.

you know, we, in my organization, have like BDRs and they're actually in the Philippines and they phone customers and they try to get new names onto our list. And do you use the stuff that prod sells? Right? Yes or no, blah, blah, whatever. Then they pass our insight guys who try to massage it any opportunities that it goes to the outside people. Right? There's literally no way that could be done by AI because maybe in a few years it might be able to, but,

But not right now because I mean the stuff we're selling is to like super geeky guys that drive pickup trucks and climb towers with 500 kilovolts on it and it's just too There's no way you can have a meaningful conversation. It's very very specific, right? So It can assist you but it can't replace right? We like we don't get appointment setting or anything like that. So

It's like building a deck, right? You can screw the screws into the deck with your, with a hand by a screwdriver, you can get a power drill, right? I mean, you're still building the deck. It's still your design and whatever the other area, for instance, you want to do some social media posts, right? And it's like, okay, well, you know, this, this week's topic is on this or this month's topic is on that. I mean, if I say to myself, Glenn, give me 30 ideas that I can talk about this month on sales growth, right? Or on funnel management.

I mean, I could come up with two. If I need to come up with 30, I would take a month, right? But AI can give me the 30 in a few seconds, right? And you could even say, write all 30 posts for me. And I mean, people would all unfollow me if I just posted those. You have to then humanize it, right? And you have to socialize it. And so the research and prep part is amazing.

But also the other areas like any new contracts we drop into a legal element and it looks at all the points, insurance and terms and termination and liability and it says, look at this point, look at this point, this point's one way, it's not a two way clause, et cetera. And I mean, I don't really wanna read 80 page documents ⁓ and so it helps with that.

And so, and also I'm not a strong financial accounting guy, right? Like, mean, I'm generic knowledge, but I'm not a CFO. And so you can put your financials for this year and last year and your cashflow state and everything. And you can say, can you give me some advice on, and it comes up with amazing insights into that, that you'd have to hire a $250,000 CFO.

To give you right and nor do you need them full-time? But you can still get the value right and so so it's an amazing assistant and And that's the way we're using it and that's and we've gotten incredible ⁓ Incredible value out of it, right and so Yeah

KK Anderson (13:12)

love that analogy. it's Mark and I talk often about how it's almost like sales is in a giant pendulum swing, right? It's, you know, we've always heard people buy from people they trust, right? Over the last, 10, 15 years, the AI sales tech world has exploded. have every kind of engagement platform, CRM, MarCom.

Glenn Poulos (13:24)

Yeah.

KK Anderson (13:34)

every kind of tech you could possibly want to support sales and marketing. And it almost got to a point where everything was so automated and so robotic that, you know, we lost the humanness, right? And now here we are on the other, we've swung all the way back thanks to AI. And, you know, it's like AI can speed things up, but trust still closes deals. And so, you know,

Glenn Poulos (13:46)

Yeah.

Yeah.

KK Anderson (13:56)

I love this analogy, this idea that AI should be your assistant because what must always stay human is the connection. I've quoted him before, but Rory Baden who runs Brand Builders Group, he always says that your humanness is now your greatest uniqueness. That's awesome. Yeah.

Glenn Poulos (14:00)

Yeah.

That's awesome. awesome.

Yeah. The, saw an interesting spec this morning where.

And it really resonated with me is that YouTube now is spending the most of its time filtering out all the AI clips because, and, and I'm like, really? And then it went on to say like, you're probably still seeing a ton of them, but you have no idea how many they're filtering out of the babies in danger. You know what I mean? And all the baby dancing and, and the, there is obviously the AI stuff, right? Or like people lying with tigers and bears and things, and it's all AI generated and it's just polluting YouTube.

to the point where they're seeing some of their core user base like log off because there's no longer, there's no longer a value. It's just like, this is all AI. I'm not getting anything from it. It's not even real. Like I don't want to be a part of it. Right. So YouTube's like, uh, addressing that as much as they can, but you, individual can use AI to create an amazing content that isn't babies dancing on gorillas or whatever,

you know, and get a lot of value out of it, right? But it has to be human. Yeah. Yeah.

KK Anderson (15:12)

and you make it human, you make it human and it's super powerful.

I couldn't agree more.

Glenn Poulos (15:18)

Yeah.

Mark (15:20)

All right,

well, we're coming towards the end here and we're moving to the area that KK and I love the most. And that's some of the rapid fire questions that we do with every guest. They're all almost always the same or very close to the others. So first one, what was the first product or service you have ever sold?

Glenn Poulos (15:23)

Okay.

So the first product that I sold was probably when I was nine, I got a job at my parents' motel. We lived in a motel. Our house was attached to the motel. And I sold rooms to strangers coming in off the street that needed a place to sleep. my second job as a teenager was I worked in a jewelry store selling jewelry and stuff like that.

KK Anderson (15:59)

Natural born salesman,

Glenn Poulos (16:00)

so.

Mark (16:00)

and what Glenn, that brings me and makes me think of the show Schitt's Creek. So if you haven't seen that.

Glenn Poulos (16:06)

So yeah, exactly the motel was exactly like Schitt's Creek, except our

motel, our house was at the end, not in the middle. ⁓ but that's, that's where we, that was my life growing up, was living at Schitt's Creek. Absolutely. Yeah. Yeah.

Mark (16:17)

That's fun. That's fun.

KK Anderson (16:19)

That is awesome. Okay,

what is the biggest mistake you've made in your career and what did you learn from it?

Glenn Poulos (16:25)

So, well, the biggest mistake I made in my career was I sold my first company on an all stock deal. And before the stock, before I had a chance to sell the stock as an insider, the company went bankrupt and I lost millions of dollars and gave them my company for free. So I realized that when you sell your business, you need a mostly cash deal. So.

KK Anderson (16:46)

it's hard to hear that.

Glenn Poulos (16:46)

Yeah. So that

was why I started Gap Wireless because I sold my first company for quite a bit of money and we had three partners, but we only took stock and the company ended up having a lot of problems that we didn't realize or investigate, I guess. And they went bankrupt before we had a chance to sell our shares and we ended up broke basically. yeah, horrible story. ⁓

Mark (17:05)

Yeah, but I'm

KK Anderson (17:06)

like you redeemed

Mark (17:06)

sure it was the baseline of all your success afterwards. So cool. Best piece of advice you have ever received from a mentor or a business partner?

KK Anderson (17:06)

yourself.

Glenn Poulos (17:17)

I guess, you got to learn the skills you want to learn how to follow up, ⁓ you know, you want to do research and rapport and whatever ⁓ the tools evolve over time. ⁓ But the base skills stay the same. You need to be good at the basics, right? it's

Mark (17:32)

Yeah, you know that

that really resonates with me. I kind of remind people of that and remind myself of that. Maybe too much, but it's I mean the basics really drive everything else from there.

Okay, I can't take this one from KK because it's our favorite one. Yeah.

KK Anderson (17:45)

I know, it's my favorite question. You've tried to take it from me, Mark. I'm getting in there. Glenn,

Glenn Poulos (17:50)

Okay.

KK Anderson (17:54)

advice you would give your 21-year-old self.

Glenn Poulos (17:56)

so the advice I would give my 21 year old self is that my favorite saying is you only get forever to make another impression, right? And my 21 year old self would say, no, mom said, you got to make a good first impression. And I'm like, yeah, that's right. Me. But every impression in your career needs to be treated as a first impression because imagine you're sitting beside your adversary at work.

Mark (18:15)

Mm-hmm.

Glenn Poulos (18:19)

sales territory and a growing expanding company, that's growing rapidly and people are moving up the ladder, right? You're sitting amongst your, your cohort of peers and the boss walks in and he sees you on Facebook, alt tabbing over to the CRM when he walks by and Sally's beside you and she's on the phone cranking out deals, right? A week later,

CEO walks by quietly again notices you're on Instagram you look over you see me all tab into the CRM, right Sally's bringing the bell book in another order. Who do you think is? He's moving to senior sales rep, right and so Next thing is they send you to the trade shows, your feet are sore. You're whining It's kind of slow, you sneak away from the booth for a few hours. Nobody'll notice there's enough people there blah blah blah

what you need to be doing is going into the aisle, pulling people into your booth so the boss can see it. When the, when it's slow, you want to be talking to the executives that are at the show with you, figure out, Hey, what makes, what are the five things I need to know about your product? Why are you here? What's so great about your stuff? What, how do I, how do I dominate and kill it? Right. And always be, always be making a good, first impression because that every impression is an impression and it's there,

And so, and, and that's how you go from being a tow motor driver in the warehouse to being the CEO 40 years later. And there's many examples that we see all the time in the news and whatever of people that started in the warehouse and ended as the CEO of a major fortune 500 company or huge company, right?

Mark (19:44)

Yeah, very cool. All right, let's final finalize with our last question here. And what's that one sales habit or practice that you do every day or week without fail?

Glenn Poulos (19:50)

Sure.

well, one of the ones would be, yeah, never fax the facts and never ship the shit. Right. And so if somebody asks me for something, and of course I made this up in the eighties, right. And so now I have to argue with all the other people like, well, don't think it's a fax machine. Yeah. So I'm like, well, whatever email doesn't rhyme with facts. Right. And so, but when someone calls me up and looks for something,

KK Anderson (20:11)

What the fax with you?

Mark (20:13)

Yeah, yeah, yeah.

Glenn Poulos (20:21)

I try to turn that into an opportunity to go visit them. Now, of course, I'm the president, I'm in the head office and I, United States is a big place or whatever, but it's, but generally speaking, it's a philosophy, right? Like if, if they're within driving distance and the guy from Duke energy asked me for something, I'm saying, you know what, I'm actually going by Duke and in a couple of days, can I drop it off?

And so I never fax the facts and they say, we need a demo. Can you ship it in? I go, no, no, we're not allowed company policy. We have to deliver all demos. You have to set them up, plug them in and make sure you can push the buttons. Then we'll leave it with you. Right. And so, because what ends up happening is, is that you ship those demos. And oftentimes when you go to pick them up or they ship them back, your, your packing tape wasn't even opened. Right. And so never fax the facts and never ship the shit.

Yeah.

Mark (21:09)

Great.

Well, Glenn, this was a pleasure and thanks so much for taking the time with us. Thank you again for joining. Thank you, KK, for being my co-host and thank you to our incredible audience for being here every week like you are. 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, Glenn Poulos joins Mark and KK Anderson to break down what truly drives success in complex enterprise B2B sales. With over 40 years of experience selling technical solutions across telecom, wireless infrastructure, and power utilities, Glenn shares the practical frameworks behind building trust, mapping decision processes, and creating repeatable sales performance.

Drawing from his book Never Sit in the Lobby and decades of hands-on leadership, Glenn explains why buyers in complex sales are not simply purchasing products. They are buying safety, trust, and confidence that their decision will not backfire. The conversation explores how to slow down early, uncover real risk, build consensus across multiple stakeholders, and implement disciplined follow-up that keeps long-cycle deals moving forward.

If you are leading an enterprise sales team or looking to scale predictable revenue in complex markets, this episode delivers actionable insight you can apply immediately.

What You’ll Learn:

• Why complex buyers prioritize safety and trust over price and specs

• How to build trust early by slowing down and asking better questions

• The importance of mapping decision makers and influencers in enterprise deals

• How to prevent deals from stalling due to unseen stakeholders

• The habits that create sales repeatability and predictable results

• Why disciplined follow-up is a competitive advantage

• How to coach sales teams before, during, and after every call

• Glenn’s philosophy of greed-based learning and how it accelerates product mastery

Key Topics:

• Trust-driven selling in high-risk B2B environments

• Mapping enterprise decision processes

• Mutual action planning and consensus building

• Sales discipline and behavioral consistency

• Curiosity, preparation, and active listening

• Scaling sales teams through repeatable behaviors

• Coaching frameworks for enterprise sales leaders

Guest Spotlight: Glenn Poulos

Glenn Poulos is an award-winning author, sales expert, and serial entrepreneur with more than four decades of experience in complex B2B selling. He is the co-founder of Gap Wireless, which he scaled from startup to a multi-million dollar distribution business serving North America’s mobile broadband and wireless infrastructure markets.

In 2022, Gap Wireless was acquired by the organization, where Glenn stayed on as Executive Vice President and General Manager to help integrate and grow the combined entity, now operating as NWS Canada.

Today, Glenn serves as President of ProgUSA, supporting US power utilities and service firms with electrical test and measurement equipment. He is also the author of Never Sit in the Lobby, a practical guide to winning and sustaining success in complex sales environments.

🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping enterprise sales, go to market strategy, and revenue growth. Subscribe wherever you get your podcasts.

Mark (00:31)

Welcome to today's episode of Selling the Cloud podcast. I'm excited to welcome Glenn Poulis, an award-winning author, sales expert, and serial entrepreneur with over 40 years of experience in complex B2B selling. Glenn is the co-founder of Gap Wireless, which he built from startup to a multi-million dollar distribution business serving the mobile broadband and wireless infrastructure markets.

KK Anderson (00:57)

and the infrastructure market.

Mark (00:59)

of North America. In 2022, GAP Wireless was acquired by Network Wireless Solutions, NWS, a portfolio company of green management. stayed on as the executive vice president and general manager to help integrate and grow the combined entity, which is now NWS Canada. Today, Glenn is president of Prague USA, a company that supports US power utilities and service firms

with electrical test and measurement equipment. Thanks so much for joining us here, Glenn, and welcome.

Glenn Poulos (01:31)

Thanks, Mark. Great to be here.

Mark (01:32)

Cool, so today we'll explore four critical themes. First one, the core of complex B2B selling. How deals really get done and when the product is technical and the risk is high, how do you make sure that you build very strong efficiency into your selling model? Building sales repeatability. The habits and systems that make results predictable.

Scaling and distribution business. We're gonna go a little deeper in that than we normally do. But really from startup to exit in the telecom and technology sectors. And then AI and technology and sales. Using tools without using the human connection.

Topic one, just start with the B2B selling model as a whole. Glenn, your book, Never Sit in the Lobby, is full of field-tested wisdom from 40 years in technical sales. When you're selling complex products, whether it's wireless infrastructure, equipment, or power utility testing solutions, what fundamentally determines whether a buyer says yes or ultimately walks away?

Glenn Poulos (02:32)

Great question. So, and we're talking about complex sales, right? So, right. Okay. Yeah. So, you know, complex sales is a little different than just, you know, box selling or when you're just selling commodities like printers and computers or something. And, you know, when, when someone's buying something that's complex, right, they're not really buying a product.

Mark (02:36)

We are. Yes.

Glenn Poulos (02:52)

I always like to tell our people they're buying safety and solutions, right? Like they've got a problem. It could probably be solved in many ways with a complex solution, right? And it, and they're buying the safety that it, the, that decision will work, won't blow up in their face. No one's going to get fired. That's where the old, nobody got fired for buying IBM or Hewlett Packard came from, right? And that someone will stand beside them when things get hard, right? The specs matter.

but trust matters more, right? That's the most important thing is the trust. And if a buyer doesn't feel safe saying yes, price doesn't become an issue, product doesn't become an issue, you're kind of dead in the water. And that's just a little,

Looking back, it's like that's why a lot of times people would say to them, so I can't believe I didn't get the order. Like I had the best product, I had the best price, I had the best delivery, but they didn't trust you. rather, and again, I love saying, nobody got fired for buying IBM, right? They knew IBM was going to be there even if they were twice the price. And it's like, you know what? I'm going to buy IBM. Then I don't have to worry about it. I can say, Hey, I bought IBM. What do you want from me? Right? So that's kind of my first part of it.

so the question is like, how do you build safety and trust, right? That's the key, you know, and so one of the key things that I always say is, you build it by slowing down early, right? You got to ask better questions.

Listening more than talking the old God gave you two ears and one mouth you do the math, right and ⁓ the so listening more than talking, know, and you want to you want to be open honest and upfront about the risks, right and Challenge them with the risks a little bit so that they're out there and you're discussing the real risks that are in play and when the buyer you were trying to establish report to the point where the buyer feels feels you're helping them and not pushing them to buy

Right. And so that's, that's, that's one aspect of it. Right. And, you know, some of the biggest mistakes people make are, you know, pushing price too early, trying to dive into specs for bigger, faster, wider, deeper, 20 % cheaper, you know, all those kinds of, you know, salesmen kind of things. Right. And pitching before understanding. And yeah. So.

KK Anderson (04:53)

So in a complex sale where it could go on for six to nine months and there's lots of dollars at stake as we were just discussing, what are some tricks or ways that you teach or talk about building consensus as you go through the sales process, as new people are added on into the conversation, as complexities increase?

you know, everyone's got a different opinion. Like what are some ways that you build, build consensus, if you will. ⁓

Glenn Poulos (05:20)

Okay, so

or get to the order or whatever, right? I guess is yeah. So first, you got to understand the risk, right? Like that's the you got to present it to the customer, you got to present what the risks are to them and getting the job done. And you have to understand what the risks are to you and presenting your product at like your solution. You know, as being the as being the solution, right, you have to always remember early on and throughout it that buyers are not afraid of the price.

And that proves itself out by just looking on the road and there's people that are driving Toyota Corollas and people that are driving Mercedes Benz S-Class, right? And so clearly some people just want to spend more on a car, right? And so they're afraid of being wrong, making the wrong decision. So you got to ask questions that uncover ⁓ what failure would look like if they make the wrong decision and who gets the blame if it happens, right? You're trying to identify that kind of stuff, right? And then second,

This is so important, right? You wanna map the decision process, who influences, and there's many models and sales strategies out there. I don't teach these, but like the challenger model and what have you, where you're identifying the technical buyer, the financial influencer, the key decision maker and what have you. But you need to know, ⁓ especially the way I explain it to people is you have to look at the dollar value of the solution that you're selling.

Let me, it's 50 K 500 K 5 million, 50 million. Right. And you have to say in the company that I'm selling it to who's signing that check, who's signing the PO, the authorization, the final, where does the buck stop? Right. Because if you're selling something that might be, you know, let's say, you know, 250 K and it's a $5 million company, it's probably the owner that's signing it. Right. But if it's, if it's a 250 K deal, but it's a $5 billion corporation.

with offices around the world, chances are some vice president, regional manager, finance guy, whatever you need to map out and know exactly where you got to go to, find out why and where it's stuck. Right? So you're mapping the decision making who's the influencers, who decides and who could stop the deal. And, you know, and most of the time the complex deals fail because you ignored.

the person you didn't know about or you were surprised late in the game who that was and that you never talked to. And sorry.

KK Anderson (07:32)

I think the key word

I'm hearing you say, Glenn, here is mapping. And we are huge fans of the idea of a mutual action plan or map, right? And so, and what's great about that is that not only are you mapping out the strategy of what's going to happen over the next six to nine months and who needs to be involved and who can say yes and who's going on vacation when, so you don't, you're not shocked at the end of the quarter when you're not getting a signature because you're

Glenn Poulos (07:42)

Nice. Yeah, good. Yeah.

KK Anderson (07:58)

You know, the signer is in Barbados, right? But the trick I would think is, and I believe, is making sure that it's mutual. And so to the extent that you can really build trust by saying, hey, here's our plan, you know, when you have a champion, I think that action of creating a mutual action plan helps to really build that trust and build that relationship. And then as you're bringing new people in,

it becomes easier because you're all singing from the same song sheet.

Glenn Poulos (08:23)

yeah, for sure. The there's a funny story in my I always like to say shameless plug for the book, right? But in my book, right, there's a story about a guy that sells high value tow motors, right? Like our forklift, some people call them. And these things are massively expensive machines, right? And $120,000 or whatever. And so, in the stories about a guy who shows up, he and he's trying to sell a company

tow motors, right? And he works for Toyota. And so he looks at the organization and he says to himself, so they need like four machines. That's like half a million dollars. It's probably the CEO that's gonna, that could be the CEO that signs off on that, right? So what does he do? He calls the CEO and he says, hey, it's Glenn from Acme tow motors, right?

You know, we want to show you the, these tow motors, they, know you're using Kawasaki, but you know, we'd love to get these in for a trial or whatever. the guys, what are you talking about? Glenn? says, I don't get involved with tow motors. the vice president of warehousing is responsible for all that stuff. That's Jack. I'm like, all right. Okay. Yeah. Fine. No problem. Let me give Jack a call. So call Jack.

Jack, it's Glenn. was just on the phone with the CEO. He told me I really needed to get your attention. We've got these tow motors, right? We know you're looking at a few, you know, know you're a coil stock user. We want to show you the Toyota. says, Glenn, stop wasting my time. says, I don't get involved in that stuff. Right? I've got a director of warehousing. That's Bob. Right? Why wasting my time? Bob, Bob, I've been on the phone all day with the CEO, the vice president. They told me if I don't get these machines in front of you, you know, lickety split.

Mark (09:41)

.

Glenn Poulos (09:53)

He's going to have my head. Right. And so, and he's like, glad, come on. I'm a director. I don't have time to look at tow motors. You got to talk to the warehouse manager. You know, that's Jack. Right. So Jack called Jack. Yeah. Of course, Jack refers you to the shop steward or whatever the floor manager or whatever. And before you know it, you're bringing in the tow motors. You say, look, I've been on the phone with the CEO, the vice president, the director, the manager, the, you know, the foreman. And now, you know, here they are. Right. So then you bring the machines to the, to the work.

The whole idea behind that story is that at any point you can call anyone in the stack and figure out where the deal's stuck, right? And so, and one of the things I always like to do, and again, this is a metaphor, right? But it's very valuable and I've used it my whole life, right? Is he call the CEO and you say, look, I know you don't get involved in this stuff, but I got to, you know, I know you're putting half a million dollars of machines on the floor. got my machine down here and we're doing circles around Kawasaki right now. Like you need to come down here and have a look at this. And he's like,

I need two minutes. That's it. And you know what the guy's saying? I'm tow motor ripping around my warehouse, brand new, whatever. I'm going to come have a look. And the CEO walks in and the, you know, all these people are like, what the heck's the CEO doing here or whatever. Right. And, but at any point you can call the CEO and say, why is my deal stuck? And then he says, well, Glenn, he says, I forgot to tell you, know, we have a deal with the national deal with Kawasaki and it doesn't expire until 2027 and

And I mean, you want to figure that out from that guy as soon as possible. And hopefully before you delivered a demo or whatever. And, ⁓ but I like to try to give people real world examples of how it plays out and, what happens on the opposite side when people don't do it right is, you know, your sales guy says, ⁓ I, you know, I got an appointment to do the demos and it's now with the powers that be. Right. He, gave his report to the powers that be.

He sent it upstairs, right? And all that stuff. I'm like, when salesmen tell me that makes me want to like blow my brains out, right? I'm like, who's the powers that be? You know, the people upstairs, right? And I'm like, no, those are the people that are buying your competitor. And you're going to come to me in a few weeks and tell me you lost, right? If you don't know that everyone in the chain and you can't call them, then you blew it. And the problem is you have to start at the top.

and go down because you can't like start with the foreman and then he gives you the old powers that be and then start calling up the stack and alienating the guys below, right? You want to be pushed down, not up, right? And because, you know, it's like, how dare you call my boss, you know? And, and so that's like a real world ⁓ scenario of how it can play out in a way that people can relate to, right? So, and ⁓ yeah.

And so I kind of got a little off topic. The other thing was, you you were asking me about, you know, how do you, how do you ramp it over time? Right. And, know, you, you always want to make sure all the trust is built before the brochures in the, and the pitching and the, know, you want to be sharing your insights and then you want to be playing to what you've learned. And you want to, you want to demonstrate and, and prove out only to that. Cause oftentimes mistakes I see guys make.

is like a good example would be myself, but don't make the mistake of using yourself as marketing data because you'll probably be wrong. But when it comes to cars, I love Mercedes-Benz, but Mercedes-Benz is known for the speed and the AMG ⁓ motors in the car, and there's a lot of ⁓ very fast

and very powerful cars, but that's not why I like Mercedes, right? I don't drive them fast. I mean, I do whatever the, whatever the proportional amount over the speed limit I'm able to drive is that's what I set the cruise at. And I, and I never, don't, you know, I'm not worried about dropping it down into third and going, you know, I'm what I like is the luxury and the comfort. I don't care about the speed. So, but most salesmen would start laying on 500 horsepower, dual torque, overhead cam, dual turbos, you know, new zero to 60. don't care.

I'm already lost and I already know that you've not built rapport with me. Right? So how is it, he's not presenting to, you know, to sell $120,000 car to someone, you know, in the right way. Cause he didn't figure out what part of it's important to me. I don't even need to hear about the speed or the motor size. I don't actually care. You know, and it's the same with many, many things, you know, and, but people are

they're scared and nervous. And so they kind of like want to drop back to like the training, the bullet points they learned in the training class. You know, we do this, we do this, we do this, we do this, right? Whereas you want to be stopping talking and start listening. What is it you need to do with these? Why am I here? What is your biggest problem you're trying to solve? You know, is it quality throughput, timing, speed, you know, power, you know, accuracy, know, resolution.

Whatever, you know, so sorry, I rambled. I said it.

KK Anderson (14:40)

makes perfect sense. It really does. And

like it, this kind of is the perfect bridge into our second topic, which is around building sales repeatability, right? And the habits, you talk a lot about habits. As a matter of fact, on LinkedIn, I reposted one of your posts this morning around the habits and the systems that make results predictable. And so in your book, you outline

57 winning sales factors and that's a lot of variables. And so when leaders hear that, their first reaction is probably something along the lines of how do I make 57 factors repeatable? So if you had to distill it down, are there three to five that are the most? Yeah.

Glenn Poulos (15:07)

Yeah.

Sure. Yeah. I love him. Yeah. Yeah, sure.

Yeah. yeah. And so, and just to touch on the 57 and the number, and I mean, obviously I'm not gonna run off 57 of anything on the show, but the...

KK Anderson (15:31)

Yeah.

Glenn Poulos (15:34)

But these are factors that cover the whole litany of things you have to do during the day and throughout your career in order to be successful running the business and in sales, right? And so it's selling and so it's how to get act and stay in front of your customers and be a pleasure to do business with always, right? And yet you have to be a pleasure to do business with because most big customers are repeat customers. And so it's not a one and done, right? It's not like, you can be cranky with them and get the deal and then you're good because you got the deal because

All the customers I work with, they're 20 year investments of time, right? They buy with for me forever, right? And the company Gap Wireless, I started in 2007 and the first call I made, you know, was a lady named Arefa and I was still making calls to Arefa the day I left, 20 years later, 18 years later, right? and so the...

And so then another insight into the 57 is these are rules that I always follow. I don't break my own rules. Right. And so, and the book never sit in the lobby. That's one of them never sit in the lobby. Right. And we can talk about that later. If there's time. Why, why I say that. but the habits to be repeatable, I guess would boil down to as first as you want to be prepared. Right. And so you've done your research, you know, you're selling this kind of a system to this kind of a company.

What does this company do? How does this company make its money? Because they don't care about your system, right? They care about whatever goes out their back door and with the invoice and what they get paid for doing, right? And so again, a quick story. I always like to put this in the real world so people understand, well, what do you mean, right? Or it's not just hyperbole that I'm saying. It's like Xerox, right? You're calling on Xerox, right? Well, Xerox makes photocopiers.

And so I need to figure out about, you know, how they can make better photocopiers. No, that's actually not what they do. They're a bank, right? They're a finance company. They make all their money, you know, on either one leasing you a machine or two, selling you costs per page, right? They don't come and tell you that that photocopier is 40 grand. They tell you it's four cents a page, eight cents a page, nine cents a page, minimum thousand pages per month, you know. And so

You need to understand how the company makes money. So you want to be prepared, right? ⁓ You know, so, and you want to keep and always be prepared, right? Second thing in the repeatability stack is, you know, discipline follow up. And so this is where people get scared, lazy. They're just averse to it. Right. And so, so often you say to him, like, did you follow up? And he's like, yeah, I, I, I call them.

And okay, did you call him? Okay. Did he answer? No. I left the voicemail. Okay. Did he, what'd you say on the voicemail? And you know, maybe he says it and again, there's rules on leaving voicemails in the book, but, then I'm like, okay, well then what'd do? He says, well, I sent him an email. Okay. Okay. Did he reply back? And no, no, he didn't reply back. And so I'm like, okay, so let me get this right. So you emailed the guy, didn't reply. So you call them, left a voicemail. He never phoned you back. And so, so basically you'd never talked to the guy.

Right? Kind of thing. But you have to, you have to be able to figure out ways and means to be able to follow up and stay on top of it. And what ends up happening is, is, know, you call him, he doesn't answer. So you send him an email and then you say, follow up Monday, right? Monday comes at a fight with your spouse. You're not in a good mood. You didn't get enough coffee. You don't really feel like making the call. You snooze it to the next day. And then the next day you have meetings. You're like, I didn't do the call. Damn snooze it to the following Monday. Now you're two weeks away.

Right? Like, I mean, that's not discipline, it's avoidance and it happens like a thousand times over every week with a thousand salespeople. Right? And so you want to be disciplined. and whatever that means. Right. And, you know, and the deals are always one after the meeting. Right. And so, third, you want to be taking good notes. You want to be, and then reflecting on what's happened, what's happening.

you want to be reviewing sort of the conversations and then looking insights. And that's where I teach, sympathy, empathy and compassion, right. And trying, trying to put yourself in the customer's shoes, figuring out what they're dealing with, et cetera, right. And applying the right technique at the right time. and you want to be reflecting on those conversations, like I said, and taking the notes and following them up. Right. And then, and so those are sort of the keys, but some of the other elements, you know,

was curiosity and ⁓ you never want to assume, you know, there's the horror story where I in the book about me assuming something about a guy and I just made him so mad by my assumption. And I was just very difficult to establish rapport after that. Right. And and you want to be consistent. Right. You want to always be a pleasure to do business with, even when they say you're not getting the order.

because you'll get the next one or you had the one before or you want to be called back in a year from now because you don't want them to not call you because they know they upset you and they're scared of you, right? It's like, I'm not calling Glenn. Pardon my language. He snapped the last time we, you know, we couldn't buy from him because of a, you know, a minor issue and, you know, a technical anomaly or whatever, right? So that's how I beat repeat. That's how I build repeatability.

Mark (20:22)

Yeah.

Perfect, good, well, yeah, those are some good thoughts and ideas. So Glenn, you've built multiple companies and have hired and managed dozens, maybe even hundreds of salespeople over the years. When you're trying to scale a sales organization, when you're trying to bring these principles into a team, how do you transfer what's in your head and in your book to the team? How do you make your process

you know, more easily teachable.

Glenn Poulos (20:50)

So.

Well, you know, how do I transfer? mean, you have to break it up into the behavior that you want and not just the talent, right? So repeatable behaviors create talent of itself, right? That's why when you look at sports people and all that, they're always doing the basics, right? You know, it's like, they're like NFL players. Why do they have to keep doing that same thing with the running with the legs and the tires? And because, you know, because they're building, they're building the talent through a set of behaviors, right?

So, and you you wanna be teaching what you do before, during and after every call, right? So we're gonna go in there, we need to figure out what it is the problem is, know, da da da da. So then you're trying to coach them during the call. And then after the call, you're like, Jack, what went wrong on that call?

Right. ⁓ I was talking too much. didn't, I saw there was an opening. didn't take it. You know, we could have got a referral to that. You know, he kind of deflected that it was another team was involved, but you didn't get any names, you know, so you want to be, you want to be, coaching before, during, and after. Right. and you know, I always like to say, you know,

Like the methodologies are the frameworks, but the winning factors are the behaviors that you follow. And you can follow a methodology and still lose because you, I would say you ignore the basics like respect, timing, preparation, follow up, what have you, right? And they all build on each other and compound into being more of a disaster the more you fail at that, right?

And so, you know, and then you're like, then the question is like, how do you pass, how do you teach people and how do you pass it on? Right. And so one of them, that's a highly personalized ones, it's from the book, right. It's my, my philosophy of greed based learning. Right. And so, and again, I hope, hope I'm not going on too far if I'm spending too much time on each one of these topics, but, greed based learning is the key to how I've sold technical products for 40 years. Right. And I, and I realized that.

you know, a long time ago and, and I allow it to, I allow it to, to work in my day to day, you know, behaviors, right? So what greed based learning is, is that, and again, I use an analogy, I love to use buying car analogies because everyone has a car. And so

Like I told you earlier, I don't care about the horsepowers and stuff on cars or whatever, right? And don't even actually care. I just want to be comfortable in a nice car and whatever with the gadgets and the cruise and all that. Right. But, you know, and so I don't really know a lot about cars where other guys know every spec off the top of their head. Right. But every four years, you know, I get a new car or something like that. Right. Well, you can bet for the, for that very small snippet of time. And for me, I'm probably going to be looking at, you know,

Mercedes, BMW, Volvo, something like that, right? And you think I can't go home and talk to my spouse and spout off every speck of those cars that I'm looking at off the top of my head with little need for memory, right? And it's a thing that I call, that's why I call it greed-based learning because my greedy little nature knows I'm getting a car at the end of it, right? And I'm able to absorb those facts painlessly and effortlessly.

Right. Because I'm getting something at the end of it. Whereas if someone just said, here's a 40 car manufacturers in the, or, car companies in the U S right. Learn all the, learn all the facts about all these 40 cars or whatever. be, it would be categorically impossible for me. There's no win in it for me. Right. And so, what you want to do is you want to sort of defer your learning until it's relevant to something where there's something in it for you. And then it becomes effortless. Right.

You're selling a million dollar system to a company you can bet that you're going to be able to remember the facts because you know what your commission is on it. Right. And so I show these guys how to allow greed based learning and gals to in their, in their career. Right. And so it's just a little, a little gamification on the, on, on learning that I do. Right. and if I have an important call with an important piece of equipment on a company and I don't really know the box,

And whatever I'll call the manufacturer, I'll call the product manager. I'll say, give me the five things they need to know in order to be a rock star with this product. And if I get stuck, I'll call you from the, from the customer site. And, and they're like, well, it's this, this, this, this, and this, right? And I'm like, look, I'm not the expert, but these are the things, you know, and then you're again, you're probing and learning and what have you. Right. So, that's the basics of it.

Mark (24:52)

No, think

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, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership.

Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor expectations.

The conversation also explores what executive vetting really looks like at the senior level, how boards assess integrity and credibility over time, and why understanding context behind results matters more than headline numbers. This episode is essential listening for CROs, CEOs, and revenue leaders aspiring to board seats or the CEO role.

What You’ll Learn:

• Board Governance for CROs: Why sales leaders must understand how boards think and operate
• Investor Empathy: How understanding investor pressure builds trust and credibility
• Learning Over Bravado: Why boards care more about why results happened than confidence alone
• Risk Awareness: How governance thinking changes how CROs evaluate decisions and tradeoffs
• Succession Planning: Why boards expect leaders to plan for a future beyond themselves
• Board Readiness: What boards actually look for when recruiting sales leaders as directors
• Executive Vetting Reality: What senior leadership evaluation really includes
• Integrity Signals: Why honesty about misses builds long-term executive trust

Key Topics:

• Board governance through a sales leadership lens
• Operator mindset vs investor mindset
• Risk management and risk of inaction
• Stakeholder alignment beyond compensation plans
• Succession planning and leadership maturity
• Board selection criteria for sales leaders
• Executive search and forensic referencing
• Ethics, credibility, and long-term reputation
• Contextualizing revenue performance and growth
• Preparing for CEO and board-level roles

Guest Spotlight: Jason Baumgarten

Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he advises boards, investors, and executive teams on leadership selection, succession planning, and governance. He has led more than 250 CEO and board transitions and brings deep expertise in evaluating executive readiness, integrity, and long-term leadership impact.

Resources & Mentions:

• Spencer Stuart
• Harvard Business Review: How CEOs Build Confidence in Their Leadership
• Board governance and executive succession best practices

🎧 Listen now and follow Selling the Cloud for deeper conversations on executive leadership, governance, and what it truly takes to move from CRO to CEO.

KK Anderson (00:31)

Let's talk about board governance for sales leaders. Jason, sales leaders are, as we've talked about, they're heads down. They're working on pipeline. They're working on deals. But investor expectations are ultimately what shape the pressure that's behind the number and behind the quarter. so talk to us about why.

should sales leaders care about board governance? What changes when they start thinking like the investors instead of thinking just as operators?

Jason Baumgarten (00:56)

So it's hard. I don't have a perfect one size fits all question because obviously every situation is different and every sales leader and company is in a different position. But I would say going back to this concept of empathy of the individuals, if you're an investor that has to return to your LPs, you've got a job to do. You're showing up and trying to explain how this investment is going to drive LP returns. And I think the first and foremost thing is for people to understand that individual connection that somebody showing up in your boardroom has.

Like why does it matter to them? what's driving their anxiety, their pressure, their sense of, combated and this at times or, or, skepticism that you're doing good job. So that's one. think the second thing is really bringing that mindset of what have we learned, not just what have we achieved. the problem is half, I would argue frequently sales leaders when they are successful, they have no idea why.

And when they are unsuccessful, they have no idea why it's like I walk into a CEO's office and they say, look, the stock price is up. And I'm like, why? It's a good rumor going around. So I think the reality is it's really important to hit your numbers. It's even more important to know why you hit your numbers, because that allows you to do it again. And when you don't hit your numbers, your board and your investors are going to be disappointed. But the critical question is, can you understand why?

and articulate what you're going to do about it, even if you don't have the perfect solution, you can bring them into the problem with you and say, here's what we believe happened. Here's now what we're trying. If you have other suggestions or people that can help us unpack this, we're all ears. I think the people who often lose their boards are the ones whose confidence overpowers curiosity or humility. And they come in just sort of

claiming that they're going to hit their numbers next time. Because the problem is, if you succeed, great. But if you miss again, you've now lost the confidence of the group. And the problem is, you don't have perfect control over your outcome, right? You could walk into a market that's falling, and you haven't figured out that it's falling yet. So what are you going to do to sort of unpack that? Now, you know, listen, at the end of the day, nobody likes to be told that the numbers aren't good. But they want to they want to understand why too, because they don't want to be surprised.

if it's a bigger problem or it's a structural problem that they don't understand. And salespeople are often the tip of the spear because that customer intimacy, they understand. But for example, are you seeking out that information? Are you trying to figure out what went wrong? if you were sure you were going to close a deal and you didn't, are you really honestly asking what went wrong so that you can diagnose it? Or are you trying to explain away the miss?

And I think people get caught up in the game of ⁓ performative explanation of like, let me look good explaining the miss as opposed to being genuine and saying, I put the wrong person on the deal, or I was overly optimistic and I didn't realize we actually had five competitors well positioned and I thought we had won or our pricing was a total miss, right? Whatever it is,

really being honest about trying to figure that out, I think goes a long way versus trying to, use bravado or confidence to convince them that it'll just be better next time. Because if you're right, great, but you don't really build your case as an executive. Whereas when you can really bring them into what happened and what you've learned from it, what you're going to try differently, what the team's trying differently, you build an enormous amount of trust and confidence that you're on.

that you know what you're doing and you're ready to tackle it again.

Mark Petruzzi (04:13)

So Jason, what does thinking about governance actually mean for a working CRO? How does it change how you run your organization?

Jason Baumgarten (04:22)

So it's a really good question and it depends on the governance of company, but I would say there's probably three things that should circle in your mindset from time to time. One is risk. Most sales leaders don't think a whole lot about risk. They think about missing a number, but they don't think about what is the risk of that? What is the broader risk? What is the risk of serving a particular customer? What's the risk of a hire? So first and foremost, it's,

part of the board's role is to think about what could go wrong and how do we mitigate that. So I think when you start thinking about it with a governance lens, you do temper some of the things you might do and say, that actually could be risky. We, something bad could happen to the company if we pursue that approach. So I think that's one is just this mindset that risk matters. By the way, there's another side of that, which is the risk of inaction, right? The risk of not doing can also come back.

So I think that's one. I think the second thing is that it does get you in this stakeholder mindset of beyond the incentive plan, beyond the annual comp structure, beyond the value of your equity in the secondary market right now. What is the bigger picture of what's going on here? And what am I really solving for? There was a book years ago, probably 30 years ago called How to Become a CEO. And I always remember this line from it. said,

Your job is to make your boss look good and your boss's boss look even better. And, one of the things sales leaders should think about is, you know, the board isn't ideally is not there to pass judgment and be critical. They're actually there to help you be successful. There's nothing they want more. So how do you think about, your role in all of that and how it ties into the broader trajectory of what the company is trying to do again, so that you can connect those dots and you can, you can be a more holistic leader.

And then I would say the third thing that board spent a lot of time thinking about, and I think is helpful for sales leaders to think about is succession planning. And the reason it's important is if you've got a lot of aspiration, you're hopefully thinking about what you want to do next. But it also helps you think a little bit more about your team and how you're developing your team. And I think boards think about that because it's one of the things that, you know, probably stresses them out more than anything is not

if it's going badly, but when it's going well, that somebody is going to walk out the door or something's going to happen. And so I think showing that maturity of planning ahead and planning for, Hey, what happens when I'm not around? You know, who's gonna, who's gonna run the play.

KK Anderson (06:32)

Well, speaking of that next, getting to that next level, a lot of sales leaders say that they themselves aspire to sit on a board one day, And few understand how boards actually select members when they're looking to add a director and specifically one with a revenue background, right? Talk to us about what boards are looking for when they're tapping a

sales leader, someone with sales leadership experience to sit on that board. And then how can the sales leaders today, in succession planning, I suppose, right, but for themselves, like how can they begin to prepare and plan toward that ultimate goal of being able to sit on a board?

Jason Baumgarten (07:10)

Yeah. So I would say that there's a couple of things. One is there's, venture boards, there's private equity boards, there's distressed asset boards, there's public boards, a lot of different kinds of boards out there. So the first thing is, they're not all the same. And they're not all transferable skill sets. The more established the board, the more it's about governance, the more the board is, you know, maybe for a smaller company, then often the board is a little bit more about

I would say it's the team you can't yet afford to hire, right? It's the folks that are just, you couldn't bring them on to your executive team, but you want their assistance, you want their help, and you want them rowing on your side. So the first thing is to really understand that those are all different boards or different selection processes or different approaches. Within that spectrum, I would say the smaller boards are looking at you as more the person who's a step ahead, right? Who's seen a movie they're about to go to and they want the advice and counsel.

And in that case, it's really just about being a excellent near day job and be showing up knowing you don't have every answer and there's other people in the room are going to have good answers. And, you're there to be of service to the, to the management team and to the investors, typically investors, as you get more seen, you know, as you get more, to the established boards, either very large private equity, a pre IPO or a public board, it is a little bit more about governance. And then the question is, you know,

The way that those boards operate is typically they've a very, very defined spec. They'll come in and say, we need a, CFO who has experience in Latin America, specifically Brazil, who has also worked in Japan and who has deep channel experience and Revrec, with Revrec and channel experience. They don't come to us and say, need a good person. Right. And so

The first thing is recognizing that just because they're seeking a board member doesn't mean it's you. The second step is figuring out, when they do need a sales leader, what are the kinds of topics they're often dealing with? And how do you best position yourself as somebody who's thoughtful, who is advancing the state of the art in sales leadership, in revenue leadership more broadly, in the industry you're in more broadly, so that people see you as an expert.

a little bit beyond your current, domain or your professional experience. And then also recognize that part of the role on the board is not just to bring your expertise, but especially as you get to the bigger boards to be thoughtful about risk, ⁓ &A, succession planning, all of these other topics that boards are responsible for. Even understanding that those are the topics boards talk about. I mean, I always say to somebody says, I want to be on a board, I'm like, do you know what's on a board agenda? And they're like, no. And I'm like, well, that's a good first step, right? Like,

KK Anderson (09:32)

You

Jason Baumgarten (09:34)

And not in a bad way, but like, go to your own board and figure out, go to your board members and ask them if what they would advise, right? Do they see you as somebody who can contribute to a board, get to know your own board as a first step. I think then really thinking about the then really thinking about how do you bring that perspective because they don't, they're not interviewing you for how excellent you are at meeting a quarter or

Mark Petruzzi (09:34)

Thank you.

Jason Baumgarten (09:57)

breaking into a new account because that's not your job as a board member. They're probably going to interview you about, if they're if they're contemplating in organic growth, they're going to say, great, how have you thought about the big picture integrating sales teams at scale? How have you thought about that? Or how have you thought about advising a team that's that's, you know, going through a business model transformation or a pricing transformation? They want to see that you can think at a more strategic and advisory level versus

being a great operator. you know, and I would say, I get asked a lot about executive classes and about trainings, they will not help you get on a board. But they may help you sound like you know what a board does. And they may make you more capable if you are lucky enough to get on a board. At a minimum, find a book about boards and read it. They're usually not the most scintillating reading to warn you ahead of time, there's no blockbuster movie about governance.

said to anyone ever. But there is, you know, there's some wonderful books that take you through the legal responsibilities of a board. And if you're serious about it, you should you should do that again, not because it helps you get on a board, not because anyone's going to select your resume, because you added your LinkedIn that you read the ABA manual on boards. But because when you're talking to a head of non gov or an investor, they're going to go, this person actually sounds seems to understand what we do.

Mark Petruzzi (11:11)

Excellent. Well, Jason, I can't finish up here without having you go a little more general on all this around, landing your next role, topic four. what really matters at the senior executive level. So, you've also said out there in some of your publications that salespeople think they can BS their way to better gigs. But at senior levels, reference in

referencing gets really intense. for those who haven't been through a significant vetting process, what changes at that next level?

Jason Baumgarten (11:44)

And by the way, I wish that was only sales leaders. think many, many leaders think they can talk their way through the next role. The reality is, I mean, just to give you a perspective, for a senior executive, typically a company, you know, working with us, for example, may take 20 to 25 references. They may do a four to eight hour assessment. They may do a psychological assessment on top of that.

Mark Petruzzi (11:50)

Ha

Jason Baumgarten (12:07)

They are typically going to do a background investigative check that doesn't just say that you had a job, but they will be sending representatives to call on every courthouse in every city you've lived in to make sure there weren't cases that were dismissed that didn't make it to the digital databases. They will screen your social media posts for inappropriate comments. They will look for any shred of evidence that you have done things that are unethical.

or that will cause risk or challenge to the organization. All of that, and then there's the bevy of actual interviews. And then typically a case study or a working session, typically a few dinners or lunches or breakfast. So by the time you're done with that process, most likely they're going to find out what they're going to find out. So that's a couple things. One is how do you get a great gig be excellent at your current gig?

Second, really try to build bridges along your career. And even if you don't like somebody, don't make a big deal of it because it'll come back to get you. Third, be really upfront with anyone trying to hire you about what didn't go well and why, because they're going to find out. And so it's much better to say, hey, you know what, that job that was two years, it actually was not a success. I learned a ton. Here's what I learned. I had a boss that just was oil and water. Here's what happened. Because if you try to position it as

No, no, was really successful. And I do 15 references and everyone says you were an ogre. It's not explainable because then it's an ethical lapse. It's an integrity lapse. So that would be, kind of what the process looks like. Now, there are plenty of roles where it's, I called a buddy and the buddy vouched for me and I got the job. And, you that's awesome. That still happens. But at the more senior levels, I would say, generally speaking,

expect that level of scrutiny and process. Certainly for a CO role, if not a CRO

KK Anderson (13:47)

Wow.

Yeah, that sounds exhausting.

Jason Baumgarten (13:51)

Yeah. And by the way, even customers, I have had numerous examples in the last decade plus where somebody says, I built the so-and-so account. Well, guess what? If that CEO is a good friend, which chances are we know them or our clients know them, we're going to call on them. If you're not working right now, we're going to just ask them flat out what the story was. But if you're working,

One of the most powerful reference questions is, hey, Mark, you get called on by a lot of salespeople, a lot of software companies. Who do you make time for?

Boy, don't make, I now know you didn't mention Johnny, but Johnny's told me he's your best friend. So now I'm saying, well, Mark, you sounds like you've done a lot with these four or five companies. Is that true? No, you don't mention Johnny's company again, strike two, strike three. Well, I know you're not mentioning, XYZ company, but what about Johnny, Chris and Mary? You seem to know them all on LinkedIn. they people you really, I don't even know who that person is.

Well, now you've lost me at the company knows me. I'm important to the company and I actually have personal relationship and don't underestimate those calls that will happen, particularly investors. They will do forensic referencing where they'll take that. They'll go through your resume and look for every connection you've ever every client you've listed, every connection, everything you've done. And then the other is probably goes without saying, but the other Holy Grail is just never, ever, ever mistake.

published document, I mean, in any format, but particularly anything that is, you where you're really putting your name to that, that you did that, whether it's a degree, a job title, we've, found this recently, where people are being a little loose and fast with job titles, just stick to the facts. You don't need to elaborate. Don't put a, don't put a, P and L leader, if you weren't one, don't put a general manager, if you're really not one, don't elaborate because

You may not be thinking about it now, but in 10, 15 years, that'll catch up to you. We had an executive years ago who overstated something probably 20 years at a company, but in his official biography with the company, he had overstated something and he didn't even remember doing it. It was when he was like, you know, in his twenties and years and years later, he went to switch roles in a very, very senior role and this became a real issue for him and

his entire career almost unraveled because of this thing he did 30 years earlier. And he didn't even remember, I mean, it wasn't like he got anything from it. He wasn't trying to obfuscate down the road. He just did it unthinkingly as a 23 year old, you know, guy filling out a corporate form and it caught up with him.

KK Anderson (16:14)

Wow. So speaking of the resume, you know, and sales leaders, you know, lot of, a lot of sales executives are going to lead with the numbers on their resume. So when what firm like yours is starting to dig deeper, like what are you really wanting to understand about those, like how those results were achieved? Right? Like what, what do you want? What do you want? How do you want the sales leaders to show up and talk about those results and those outcomes?

Jason Baumgarten (16:37)

Yeah, there's a few things. First of all, what was going, what was the context, right? What was going on around that industry? Are you actually showing me the best numbers you have, but they're the worst numbers of any of your competitors? So the more you understand the competitive landscape and your peer group, the better. The second is what was the momentum when you caught it, right? If it was going up 30%, now it's going up 20, you can tell me how amazing you are that you hit 20, but actually you decelerated the rate of growth. So I want to understand

what happened because that's actually a story of negative, you know, negative impact, even though it's a positive number. The third thing is do you seem to understand what you did to achieve those numbers? Right? And that's a recurring theme that you'll hear from me. But, you know, do you have clarity as to what you did? One of the most common things is people who are in jobs for very short amounts of time, but the numbers were good. They're like, Oh, yeah, I was there 18 months, but wow, we crushed it.

crushed it so amazingly, I could go on to the next role. And I'm like, let's unpack how you crushed it in 18 months, because it took you six months to find out what the name of the people what, where the bathroom was, and what the names of everyone on the team was, and what the products were all called, and blah, blah, blah. Any human being, takes months just to normalize. And then it probably took you three to six months to find your next gig. So in that short time, you were actually working enough to speed, what did you do?

And if the answer is kind of fuzzy, it's not that I worry that they didn't have a great 18 month tenure, I worry that they're so busy trying to tell me that they did something they didn't, that that demonstrates how they show up as a leader, and how they show how they show up as a as a colleague on a team. And that's way more concerning than that they didn't have an amazing 18. Anyone who's at somewhere 18 months, and probably it wasn't an amazing run. I mean, the odds are good that if you're there less than two years,

Something went wrong, whether it was up to you or not. Something probably went a little off. That's fine. Just own it. Just be like, hey, that wasn't so good. Or it was so good that it led to this next thing coming out of the blue. But also have the humility to be like, I inherited a great situation, didn't screw it up, as opposed to saying I did everything and I'm amazing, because things just take time. I mean, in 12 months, you can't turn around that much.

Mark Petruzzi (18:41)

Jason, and thank goodness that companies are doing this and focusing and figuring out how they can get senior executives that are ethical and honest and trustworthy. Because if not, who knows what our general economy would look like. ⁓ Because it's one thing if you hire a sales rep who maybe is a little unethical, you figure it out, you you...

you move on that individual. But if you hire your CEO, CRO, and Chief Operating Officer with those kind of backgrounds, it's going to come out. It's going to show up at some point. so I'm really glad to hear the, I've experienced it myself in the vetting process, but to hear you articulate it takes my understanding to an even greater level.

Okay, we just have a couple minutes left. We love doing these rapid fire questions that we do with our guests and I'm really interested in hearing your responses on these. So what was the first product or service you ever sold?

Jason Baumgarten (19:43)

I sold jewelry. I bought jewelry wholesale and sold it at street fairs.

Mark Petruzzi (19:48)

I like that.

KK Anderson (19:49)

That is so cool. How old were you when you did that?

Jason Baumgarten (19:49)

And you learn a lot selling jewelry.

I was like 14.

KK Anderson (19:52)

Really cool, wow. You knew you would be going to Stanford at that point. The entrepreneur at 14. ⁓

Jason Baumgarten (19:57)

⁓ I knew I loved business. I knew

I loved business.

KK Anderson (20:00)

Jason, who's your favorite CEO or business leader that you've worked with over your career?

Jason Baumgarten (20:05)

You know, I have so many, this one's really hard. I actually find that I learned so much from so many of the CEOs I work with and they're all amazing at certain things and they all have ⁓ foibles. I think that rather than share the person, I'll share the story. A CEO that has had an unbelievable career. He always takes the time to learn and get better. And

He's got coaches, he's got advisors, he's got, but he's just a learner. you know, he's one of these guys, it's a household name, but you reach out to him and he says, I'm busy. sitting down with a 24 year old to learn about how to do better prompting. I'm like, you're retired. What are you doing? He's, I got to get good at this. It's really important. And I just, I think there's a amazing, the CEOs who keep wanting to get better are just really inspiring.

Mark Petruzzi (20:51)

Yeah. So a resource every aspiring board member should use.

Jason Baumgarten (20:55)

their network.

Mark Petruzzi (20:56)

Excellent.

KK Anderson (20:57)

That's a good one. Okay, my favorite question is not listed here, so I'm gonna go out on the limb and say it anyway. Jason, what advice would you give your 21 year old self?

Jason Baumgarten (21:07)

Take more risk. I think that's the thing that we underestimate when we're young is that you can recover, can do, you can get a do over. People are very tolerant of youthful, ⁓ you know, behavior. don't mean behaviors in a social sense, but you know, just try to start your own company, try to join a startup that's a high flyer, try to, do something that's risky, because when you get older, it's much harder to take risk for all kinds of reasons.

So do it when you're young and within whatever is relevant to you. You might be the most risk-seeking person out there But you know, would say I think most people when they're young They squander good risk They take a lot of risk in their personal lives and not a lot of risk in their professional lives And I'd say take some professional risk

Mark Petruzzi (21:47)

Excellent. Well, Jason, thank you so much for your time, your great analysis and answers. We will add for our audience here, we'll add a bunch of show notes and make sure you get to read some of the good stuff that Jason has put out there and learn some more about him as well. yeah, so thank you, Jason. Thank you to our amazing audience.

We so appreciate you and thank you to my co-host, KK, as well.

Jason Baumgarten (22:16)

You guys were fabulous. Thank you.

KK Anderson (22:17)

Thanks, team.

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, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level.

Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as they move from execution to enterprise leadership. The conversation explores founder-led transitions, boardroom presence, customer lifecycle thinking, and why sales excellence alone does not guarantee executive readiness.

This episode is essential listening for CROs, founders, and revenue leaders who want to move beyond quota and operate at the highest levels of leadership.

What You’ll Learn:

• From CRO to CEO: The mindset shifts sales leaders must make to be considered for top executive and board roles
• Boardroom Credibility: How sales leaders can show up as strategic business operators, not just revenue owners
• Founder Transitions: When founder-led selling breaks and what must change to scale the organization
• Systems Thinking: Why understanding the full revenue and customer lifecycle matters more than pipeline alone
• Executive Readiness Signals: What boards look for when evaluating senior sales leaders
• Hiring at the Right Time: Common board mistakes when transitioning away from founder-led sales

Key Topics:

• Evolving from sales operator to strategic executive 
• CRO presence and influence in the boardroom
• Founder-led sales versus scalable go-to-market systems
• Retention, lifecycle metrics, and long-term growth signals
• Board governance and leadership transitions
• Why sales is not always the answer

Guest Spotlight: Jason Baumgarten

Jason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he leads executive search and board advisory engagements for companies ranging from early-stage ventures to multi-billion-dollar enterprises. He has advised on more than 250 CEO and board transitions, with deep expertise in founder-led technology companies, succession planning, and board effectiveness.

Before joining Spencer Stuart, Jason was an Associate Principal at McKinsey and a Program Manager at Microsoft. He holds an MBA from Stanford Graduate School of Business, serves as Chairman of the Board for IslandWood, and is a frequent contributor to Harvard Business Review, including his article How CEOs Build Confidence in Their Leadership.

Resources & Mentions:

• Spencer Stuart

• Harvard Business Review: How CEOs Build Confidence in Their Leadership

• Mark Roberge: The Science of Scaling

🎧 Listen now and follow Selling the Cloud for conversations with leaders shaping the future of go-to-market, executive leadership, and board-level decision making.

Mark Petruzzi (00:37)

Welcome to today's episode of Selling the Cloud Podcast. I'm thrilled to welcome Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stewart. Jason leads Executive Search and Board Advisory for one of the world's premier leadership consulting firms. He's completed over 250 CEO and Board Transitions.

across companies ranging from early stage ventures to multi-billion dollar enterprises. His expertise spans CEO succession planning, board effectiveness, and leadership transitions, particularly for founder led technology companies. Before Spencer Stewart, Jason was an associate principal at McKinsey and a program manager at Microsoft.

He holds an MBA from Stanford's Graduate School of Business and serves as chairman of the board for Island Wood. His thought leadership appears regularly in the Harvard Business Review, including a recent article, How CEOs Build Confidence in Their Leadership. What makes Jason's perspective uniquely valuable is his vantage point. He's interviewed thousands of sales leaders and observes what

separates those who successfully transitioned to CEO and board roles from those who just can't get there. Today we'll explore four critical themes. The sales leaders evolution from operator to strategic executive. Founder transitions building a leadership capacity beyond the go-to-market motion. Board governance for sales leaders. Why thinking like an investor makes you better at your job.

and landing your next role, what really matters at the senior executive level. So I guess a couple of things there. You really don't work hard enough or really haven't accomplished most in your life Mano man, Jason, what an amazing career you've had already.

And I'm sure you're not going to be slowing down anytime soon. So thank you. Thank you for joining us and joining us here on Selling the Cloud podcast.

Jason Baumgarten (02:40)

Well, thanks for having me. And I felt a little tired listening to it, but it was all fun in the moment and delighted to try and share some learnings from the many, many, interviews and board discussions and CEO discussions with your listeners.

Mark Petruzzi (02:53)

Yeah, and Jason, we have an audience of mainly CROs, some of the best in the business. And, you know, there's a number of them that I've already prepped to make sure that they've watched this because they're looking at the things that you do. ⁓ And I have many CRO friends who join us as well that have made this transition. So I love the, I love where we're going here and excited.

to dive in. Topic one, the sales leaders evolution. How do you evolve from somebody who's great at sales to configure out management and understand leadership, and then they really have to move to the next level as a strategic executive, often without the background, not to say an MBA or a more prominent type of... ⁓

educational background gives you all the recipe to do it as well, but many of them, you know, just they feel like they don't have that. So in your interviewing of thousands of sales leaders, what fundamentally distinguishes those who you feel can successfully transition to the CEO role or to board roles from those who just you feel maybe we'll struggle with that?

Jason Baumgarten (04:04)

Yeah, it's a great question, Mark. I mean, first of all, it sounds perhaps silly, but I start with do they really want it right? And the reality is not everyone really wants to be a CEO once they learn what that role is all about. ⁓ And so you have to start with not wanting it for ego reasons or control reason, but really do I want to do that job more than the job I'm doing today? So that's sort of step one. It's important. A of people breeze right through it, but I'm like, no, actually, do you really want it? And why do you have

thought out reason why. The second thing is, you know, sales, ultimately, I think have a sales leaders have a couple of critical advantages. One great sales leaders have real industry and customer intimacy, and great organizations are built around solving customer needs. And so if you can really lean into that proximity, that superpower, that's super helpful. The second is most sales leaders are great people leaders.

And so if you're really thoughtful about how do you lead a team? How do you lead people? That's another thing to lean in. What are the areas they tend to be less good at? Well, the first is genuine curiosity, right? One of the challenges with sales is one can become quite transactional. How do I hit my number? How do I move the sale along? How do I move the conversation along? How do I get what I want done, done? And the reality is great leaders are deeply curious. They're deeply

interested in learning about other functions, other aspects of the company. So the first thing I'd say is tap into your innate curiosity to learn about what's going on in finance, what's going on in legal, what's going on in product, what's going on in marketing, what's going on in customer success. So that as you evolve your thinking, you understand more about what's happening in other functions. The third thing is actually rising up.

and doing two things. First, think as a systems thinker about how do all the pieces of the puzzle fit together to make revenue and profit happen and get knowledgeable about that system. And then two, ensure that you are not coming across as somebody who believes sales is the answer or the cause of all problems or solutions. So those are a few of the things that I'd share. We can go into more depth on any of them.

But there's some of the high-level things if I had to add a final one, I'd say humility I always laughed that if I interview all the top sales leaders at a company that revenue will beat will go up at least a thousand percent from the interviews alone when you just add up all the numbers and of it is there's an amazing quality of confidence and You know that a lot of sales leaders have but recognize that when you're interviewing for a CEO role or for something else you've you've got to temper that a little bit with

Mark Petruzzi (06:24)

Yeah.

Jason Baumgarten (06:40)

that empathy, that curiosity, that humility.

Mark Petruzzi (06:42)

KK, I think you're on mute.

KK Anderson (06:43)

Well, that's a first for a podcast to land. Jason, really interesting what you're saying. And you've said that board members can sometimes be like Christmas lights. Like, you know, they turn on once a year, right? And so for a CRO walking into, you know, a board meeting, like, and thinking about how, how...

Mark Petruzzi (06:46)

Yeah.

Jason Baumgarten (06:46)

Yeah.

KK Anderson (07:05)

What advice do you give? Maybe they're not aiming to be CEO, but what advice do you give them around not just being seen as a salesperson? Talk to me about that. Talk to me about a CRO walking into

Jason Baumgarten (07:15)

Sure. You

know, first and foremost, it's think about your stakeholders and most salespeople do this really well. So think about who's around the board and what matters to them. What are they thinking about? What's their what did they show up worried about or excited about in that board meeting? And I don't mean conceptually and for all time Memorial, but like in that meeting, what's on their mind? What's going on in their companies? What's going on in their investment groups? If it's a public company, what's going on in their day jobs or their other boards?

What is the context? know, are you, are they walking into a new product launch being announced at your company? Are they walking into a bad quarter? So the more you start with who am I presenting to, who are these people on the other side, not just in the singular dimension of them as your board member or investor, but also the rest of their lives. So that's sort of step one. Step two is to your question of how do you appear as more, you know, how do you present a more holistic perspective? You know, I think

It really comes from that ability to connect the dots between what's going on with your customers and the market, you know, competitive point of view, you know, customers need shifting product evolution, technology evolution. So that's one. And then the other is being able to connect the dots inside the company. You know, we did this thing on, ⁓ our customer support initiative. It had this impact on renewals. This then led us to be able to change the way we're going after new logo.

The more you can stitch together narratives that are multidisciplinary, the more they start to see you as not a one-trick ⁓ answer. And the other thing I'd say is know when the answer is not sales. One of the most powerful things any functional leader can do is to say, that's a great question. I actually think the answer is in marketing or is in HR or is in finance or is in customer support.

You could give us more resources and sales, but that would be the worst place to put the capital to solve that problem. Because showing that shows that you are stepping out of your functional role to really think about what's best for the company and how you as a systems thinker would apply that capital or that resource.

Mark Petruzzi (09:15)

Jason, so in general, when should a CRO start thinking about building the capabilities beyond the pure sales, execution, sales leadership side? What's the signal?

Jason Baumgarten (09:27)

So I think there's two things that are working in tandem. One is their ambition, right? Do they have ambition to do more bigger, more complex, even sales roles or CRO roles that are broader than sales? And then have they mastered where they are? So at a very simplistic level, do they feel like they've kind of got the, you know, the training wheels off in their current role? You know, do they have sales ops team leadership, you know, forecasting

KK Anderson (09:37)

it in that

Jason Baumgarten (09:49)

all those key skills down, if they do, it's a perfect time to now start to think about how do I broaden? If you haven't got those mastered, you know, probably need to spend time there. But if you feel like you've got your quote unquote day job in good order, it's only going to make you better in your day job. And that's I think one of the things people often forget is they think, I'm doing this to become a CEO or to become a board member, or to take on more, it will actually make you much better in your day job.

because you'll start to think about ⁓ other levers you can pull with your colleagues to help move revenue beyond what's in your control. And that influence in your leadership team, you will be more effective because you won't be seen as somebody lobbying for your team's resources, but for solving, know, every function wants more revenue, more profit. So when you start solving for that, you become an enlightened sales leader who,

everybody wants to pull into their opportunities, their, you know, their initiatives, et cetera.

KK Anderson (10:46)

Isn't that the truth? Yeah. Jason, let's move on to the second topic and talk a little bit about founder transitions and building, as you've been discussing, that leadership capacity beyond just the go-to-market motion. And you have worked with many famous founders, ⁓ and you've had the ability to see a lot of these founder-led companies up close. And so I would love to hear

you know, maybe a story or two about some of your, your favorite famous founders that you've led. and then specifically like when, when they stopped becoming the primary salesperson, right. And the company starts to scale. I'm curious, like what usually breaks first, right. And just talk, talk us a little bit about some of your, favorite famous founders.

Jason Baumgarten (11:30)

So I think I've worked with almost all of them in some form or fashion. ⁓ You know, I would say that what tends to break is sleep. If I'm realistic, it's, it's the thing is you just only, no matter how amazing somebody is, they only have so many hours in the day. And so that's one. I think the other thing is that, you know, and you know, this as well as everybody ⁓ who really is an expert in sales, the one-on-one connection of an individual can only scale to so many people.

KK Anderson (11:36)

Okay, there we go.

Jason Baumgarten (11:54)

And so I think what starts to happen is that while they typically are doing more of a business development motion, more than a real scaled sales motion, they start to realize, I need some channel sales. need some indirect sales. need some marketing driven conversion. I need more tools in the basket. And then they start to build a sales team beyond them. Now, I think the early sales leaders of many companies

are individual contributors themselves. And so there's almost two evolutions. There is the first, you know, it's the founder being the salesperson, and then there's the first salesperson being the only salesperson. And then it's you as a sales leader kind of going to the next level as a ⁓ building a team, building a, you know, a model of sales. So I think that's often the trajectory these companies go through. I would say the other watch out is

Mark Petruzzi (12:28)

Thank

Jason Baumgarten (12:42)

founders who have a couple of really good early deals and think, boy, this sales thing is easy. And then they start to scale it. And they realize that that was just friends and family. And people thought it was great. Or they got some early pilots and it's not easily replicable. And so I think when you really ⁓ move from founder stage to a growth stage is when you can replicate that journey, when you know that you can hand this to someone else and Mark can go sell.

just as well as I can. Founders are always going to have a special edge, right? The reality is if a founder calls a company, they're always going to have a little extra time. It's a little easier to get through to an executive, but until you can replicate it, you really don't have a repeatable sales process. ⁓ You know, I would also say that what we're seeing now is a real evolution in how people are thinking about it, because you are also seeing ⁓ much more complex sales motions.

And in some cases that's complex because we're seeing them look more like consumer sales motions. And in some cases, much more like consulting or professional services. So we're seeing more bifurcation than for a while we were into the fairly low complexity SaaS sale, you know, and that is on the edges starting to fray a little bit in terms of just the complexity of, the heterogeneity of all the different types of products and services we're seeing in technology.

So maybe avoiding a particular person, but, you know, I think everybody goes through that wave and, you know, I worked with one leader who his startup was in the sales technology space. And that was perhaps the most incredible cause he was one of the best salespeople period. And he was one of the best salespeople for that company, even when they were at, you know, several hundred million dollars in revenue. But he realized he had other things he had to do. And if he spent all his time selling,

So what he started doing was spending more time teaching and making sure the right process was in place to scale as opposed to saying, I could do that better. Because of course, but he also couldn't do everything. had to, he had to pick what he was spending his time on.

KK Anderson (14:38)

Especially if he wanted to sleep, right?

Mark Petruzzi (14:40)

Now that Jason, that is spot on. So in some of your publications, articles that I've read, you mentioned two critical dimensions. Building the right go-to-market engine as one aspect of it. And then at the same time, readying the organization for when it's not founder led sales anymore. And they're not spending 50, 70 % of their time on sales.

How should boards in particular approach these transitions? What responsibilities do they have in all of this?

Jason Baumgarten (15:13)

Yeah, it's a great question. It does depend on this on the type of board and this, even for startups, what's the type of startup and the ambition of the startup? You know, I think the thing that boards should spend the most time on is what is the theory of the sale? Like what is the theory of the sales system that the company is starting to move towards when it goes from an individual to a system? Second, based on the data, you know, the early returns early data,

is that hypothesis or theory holding true, right? So for example, if we say, we're going to sell into this ⁓ type of executive, we believe it's get a demo, show the demo, do a pilot, you know, whatever the the march you're taking people through, is that actually proving out in the early data? And then the third thing is, is the company continuing to appropriately experiment and test whether they have the right model? Because I think it's probably the most

dangerous thing is to very early and we see this when an executive comes in and says well I've heard it I know the way to sell is XYZ and I'm gonna bring that into this startup and it isn't the right model right something is off either the ideal customer profile is off or the literal ⁓ you know Approach is off or the pricing is a little bit off Something in there is a little off and instead of catching it early. They catch it really late That's really bad for that sales leader, but it's also really bad for this

for the company. so board members can really try to make sure there's a crisp hypothesis as to here is how we're going to sell. Here is the data that's going to show us that we've got the right model. And then three, are we seeing reinforcement that we picked well, or lessons learned that maybe we've got something off and what are we doing to adjust. ⁓ And then you can start to diagnose what's going on if you're not hitting or beating your expectations, you can say, we had something wrong. And that's okay. I think

The worst thing is to double down and say, we just aren't trying hard enough. It usually is a strategy or a process problem, ⁓ not a try harder problem. You know, unless people are just flat out lying about what they're doing, but I don't find in, especially in startups, people are usually pretty excited to grow the company. And so they're showing up, you know, trying to kill it. The other thing is not recognizing that whatever works early is probably not the forever model. And

For example, there was years ago, an enormous number of SAS companies that had very low cost direct models. And they realized that that wasn't going to scale that they needed to get a more enterprise motion. And yet they built teams that were so well oiled for a particular model that when the when the growth rates started to slow down, they didn't they weren't as quick to transition or try new things. And that's a failure. The know, it's a failure of the leadership team. But

even a failure of the board because the board should have been asking those questions earlier than the executive team because the board's role is to try and look ahead of where the executive team is is reacting to right now because the executive team might be You know 70 % reactive 30 % planning the board should be the other way around and should be able to say hey I think this is going to come and hit you in a year or two years. How are you prepping for it? Now? What are you doing now? How are you learning now? So that's how I think about that board interaction early on

KK Anderson (18:14)

You know, we were just interviewing Mark Roberge this morning on the release of his upcoming book, The Science of Scaling. And he was talking a lot about, you know, an early, you know, indicator of retention around, you know, customer success. And so for a sales leader, you know, they are a CEO might be thinking like, hey, just get us more leads, you know.

get it, we just need more pipeline. Pipeline will fix everything, especially in these early stage companies. And Mark's argument was actually, what you really should be focusing on is your retention. Like, are you hitting those benchmarks that show that people, your customers are staying and you have, you know, product market fit, you have go-to-market fit, your customers are there and they're coming back and they're renewing. So, you know, talk to me a little bit about kind of your perspective on

on that idea and what are some, like when you see founders, you know, start to show maybe a lack of leadership or like you're like, I want to coach them to increase their acumen as their companies grow and scale. And you need to take into consideration things like, you know, the retention metrics, you know, more so than the sales metrics. And you said earlier, recognizing that sales isn't always the problem.

Like what does all of that make you think of? what's your perspective there?

Jason Baumgarten (19:24)

Yeah.

I mean, first of all, I think he's spot on and I'd go so far say, you know, you want your metrics across the whole consumer lifecycle, you know, the whole client customer lifecycle, because it may be showing up in retention, it may be showing up in a lack of cross sell, it may be showing up in different areas. And the point is not to say we did a good or bad job, let's understand what's going on. It may be that you're got great conversion, but with all the wrong clients. And the real issue is you're going after the wrong clients, the wrong customers.

not ⁓ that you are incapable of turning those leads into opportunities. So I think the first thing is I'm a big believer in capture the data across the whole life cycle so that you can understand what's going on with the sales approach, you know, depending on the type of product we're talking about, the, you know, the onboarding, the services side, the customer support side, et cetera. So I think that whole life cycle is critical. I think that when, ⁓

You know, when founders are finding themselves stuck, usually the answer is go talk to people who have done who are a little further along in the journey than you are and ask them for advice and counsel about what worked for them. And don't take one person's advice. Don't say, well, you know, one investor told me the answer is this metric. So I'm going to go chase that metric, triangulate different people, get a good kitchen cabinet together.

and ask different people and don't just ask peers, don't ask other founders alone, don't ask other CEOs, ask people who are in CRO roles, ask people who are individual salespeople, ask people who are in other parts of the ecosystem so that you're hearing perspectives from, you know, the person who might be junior entitled to you, but much higher than you in scale. You know, I always laugh, you can be CEO of your own business, just pop a magnetic sign on your truck and drive around and Mark's got Mark and Co.

He's a CEO done. You don't, you don't need to actually have a company to be CEO. Same thing with the sales person, right? If you're selling lemonade, you're a sales person. But if you're, you know, you could be a very junior person selling millions of dollars in a very complex way for an enterprise SaaS company, or you could be a founder who's got a big title and a lot of sense of importance, but you're selling half a million dollars. And that doesn't make you more sophisticated as a sales strategist and the person who's a

Mark Petruzzi (21:09)

Mm-hmm.

Jason Baumgarten (21:36)

senior manager at a big SaaS company. So don't just think about your peers. Think about, you talking to people in different roles and different scope and scale? And to me, that helps you understand what's going on. It also gives you empathy because when you start thinking about things like incentive plans or how to inspire the team, you also are thinking about, wow, how does that work when you've got 40,000 people?

I've got five, how does it work at 40,000? So I think the more they can get out of their own atmosphere, it helps a lot.

Mark Petruzzi (22:08)

So Jason, I'd like to take you back to the board perspective for one more question here. So what mistakes do boards typically make in the timing and structure of hiring professional sales leadership as they move from a founder led selling motion?

Jason Baumgarten (22:26)

Well, I think that I think the two biggest mistakes I've seen is they don't do it early enough. Right. There's a sweet spot. If you do it too early, you don't, you don't have product market fit. There's no point in bring on your professional sales leader. If you wait too long, things get pretty calcified before somebody has a chance to think about your incentive design, your partner design, your channel design, all those things. I would say the other piece of the puzzle is hiring somebody who is going to bring the

And if you don't, you know, you can either start with a very open mind, you know, classic beginner's mind and say, I don't know what model, but I'm going to use this recruitment to help figure that out. Or you can do the work to say, we've actually figured it out. I figured it out or your team has figured out. And we now know what kind of sales leader you need, because if you believe your PLG and you're really not, you can hire the absolute wrong person. And that's not good for anybody. And I'm a big believer that there's, there's

there's not good and bad sales leaders. There's not good and bad leaders is actually people who are the right fit for the right time. And so you need to make sure that the fit of that sales leader is what you need. ⁓ The third thing I'd say is sometimes they just over, ⁓ you know, there's a desire to sometimes signal a Rolodex and get somebody who's got a big Rolodex. And maybe because I'm in the Rolodex business, I always laugh. like, listen, if you've got a product that's solving real problems,

getting access and the Rolodex will be the least complicated thing. And people want problems solved. And so if you really have a good solution, you will find a way to those people. That is probably the least value in most industries. That's probably the thing I would not get hung up on early. And yet I think a lot of founders think that's the magic unlock. The reality is most human beings at best,

best have 100 to 150 relationships. And that's actually overstating the real quality of most of those relationships are ⁓ not preferential. Meaning if you and I have the same product and we both go, I'm not going to win it just because I have that relationship. It's really going to come down to who is the better product. And so I would say don't over bias to that concept of access.

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, Cherilynn Castleman joins Mark and KK Anderson to unpack what strong CRO leadership looks like in a time of rapid AI adoption and constant go-to-market change. As every team claims to be AI-first and tech stacks continue to converge, Cherilynn explains what truly differentiates leaders who drive real results.

This episode dives into how curiosity with AI, disciplined daily usage, and protecting selling time translate into cleaner pipelines, shorter sales cycles, and fewer end-of-quarter surprises. Cherilynn also shares practical guidance on modern operating rhythms, how to run meetings that actually matter, and which metrics prove that change is working now, not quarters from now.

What You’ll Learn:

• Building AI Fluency as a Leader: Why modeling curiosity, transparency, and experimentation matters more than mastering tools
• AI as a Daily Discipline: How consistent usage creates confidence, clarity, and better decision-making
• Protecting Selling Time: How CROs can reduce meetings and increase seller productivity from 10 hours to 15 to 20 hours per week
• Humanized Outbound at Scale: Using AI for micro-segmentation while keeping messaging personal and relevant
• Running Meetings That Matter: How 30-minute meetings, no slides, and clear ownership tighten pipeline execution
• Proving Change with Metrics: The three numbers boards and CFOs care about to fund and support transformation

Key Topics:

• CRO leadership in an AI-saturated GTM landscape
• Modeling AI curiosity and transparency across revenue teams
• Stop chasing tools and start building the right mindset
• Exact meetings, executive engagement, and decision-maker access
• Micro-segmentation by persona, industry, region, and generation
• Modern revenue operating rhythms and pipeline hygiene
• Measuring cycle time, executive involvement, and multi-threaded win rates

Guest Spotlight: Cherilynn Castleman

Cherilynn Castleman is a sales and leadership advisor who helps revenue teams adapt to modern buying behavior and post-pandemic selling realities. She is the author of Post-Pandemic Selling, a top Amazon bestseller that has been recognized by Salesforce as one of the top sales books for modern leaders. Cherilynn is also an active LinkedIn voice, hosting frequent LinkedIn Lives where she shares practical insights on sales leadership, AI fluency, and authentic connection.

Resources & Mentions:

• Book: Post-Pandemic Selling by Cherilynn Castleman
• Website: postpandemicselling.com
• Recommended Book: The Untethered Soul by Michael A. Singer
• Leadership Voice to Follow: Bill Green, former CEO of Accenture

🎧 Listen now and follow Selling the Cloud for more insights on AI-driven leadership, modern sales execution, and building trust across today’s go-to-market teams.

Mark (00:30)

All right. Let's move to topic three. Leading as a CRO in a time of intense

change. So every team nowadays says they are AI enabled, they're AI first, and everyone's sales and marketing stack just looks very similar. So from the seat of the CRO, what actually differentiates leadership right now in your opinion? Could you give us two or three weekly behaviors you expect to see

in the numbers of a CRO that is leading well.

Cherilynn Castleman (01:04)

Yeah, so a couple things. I think that if a CRO is demonstrating curiosity with AI, they are using AI, they are sharing with their team, this is what I did. I was working with the CFO for a huge company recently and they do a pricing exercise. And they normally would sit down for a couple weeks and work on this pricing exercise. And I challenged them to open AI and pull their data into their proprietary system.

And in 30 minutes, they had done the entire exercise. And so it was like, wow, everybody's going to be impressed. I said, no, it's transparency. Tell them you used AI to do it. Demonstrate, model that you're curious. If you fail, talk about that. So number one, they're modeling curiosity. Two, it's a discipline. They're using it on a daily basis. They're talking about it on a daily basis.

There are somewhere between 50 and 200 new AI tools every day. There are, when you look at go-to-market tools, there are somewhere between seven and 10 new tools every day. There's no way you can master the tools. Stop chasing the tools. It's a mindset. It's about confidence and clarity. The next thing that I would say is that ⁓ protect the selling time.

Look at your meetings and make them very efficient. Get them down to 30 minutes. The goals is most sellers sell about 10 hours a week. You want to get your sellers to 15 to 20 hours a week. And so where you're going to see this, are you going to see a cleaner pipeline, you're going to see higher exact meetings. And so those are things you want to measure is not just meetings, but exact meetings, decision-maker meters. It will shorten the sales cycles and you'll have fewer surprises at the end of the quarter.

KK Anderson (02:43)

So good. was just on a coaching call just before this podcast episode actually, and was coaching a new seller that was joining the team and was asking about the hustle and the grind and around hunting. And so we popped open Chachi BT and we put in the overall team's average deal size, average win rates, know, sales cycles. And he...

figured out that he needs to make 6,700 calls in the first six months to be able to get the number of opportunities in his pipeline to be successful. And he was like, what? 6,700 calls. But you break it down into a daily rhythm. And you break it down into who you're targeting. And you can use AI for those things to get smarter and hone in on offers based on personas and POVs. It's interesting.

Cherilynn Castleman (03:24)

Absolutely.

It is. And the other thing is that

the goal, and so I think Mark mentioned this, we're opening emails and we're like, yep, AI wrote that, yep, AI made it. And so what I challenge people to do is, yes, you have to do your volume, but what if you spent 15 to 30 minutes every day sending a couple better emails? Where you actually, you know, and so, then, yes, if you sent a humanized email, I love it when every once in a while I get an email and I'm like, yes.

KK Anderson (03:50)

human

Cherilynn Castleman (03:56)

this lands. We all know what those feel like. We'll learn to send those kind of emails. And if you're not sure, I tell people, email them to yourself and then open it on your phone. If you won't open it on your phone with the subject line and the first sentence, why would anybody else? So send it to yourself, look at it, and yes, get your numbers in, but spend time figuring out how to craft.

better emails and micro segment because once you've done your micro segmenting, you can do emails to Gen Z, Gen Y, Gen Alpha. You can do it by title, can do it by industry, West Coast, East Coast. AI will do all that. Do all your micro segmenting and then you're now doing a more humanized outbound and I promise you, you'll hit your numbers and make fewer and send less noise.

KK Anderson (04:43)

meaningful, more meaningful

outreach, yeah. Okay, so you said something a second ago. You said when Mark was asking about the CRO and leading well, you said less meetings and the meetings that are, having the meetings that are meaningful. And nobody likes a meeting, everybody hates a pipeline call, we know that, right? So like what in today's day and age, like what is like,

Cherilynn Castleman (04:46)

Yeah.

KK Anderson (05:05)

What are the non-negotiables, but what gets cut and what changes and what, talk to me about that operating rhythm, is it changing?

Cherilynn Castleman (05:11)

So I think it is. I think that, so what I encourage people to do is do 30 minute meetings because of AI and technology and Facebook and Instagram and everything. The 10-minute spans are very short. So do a rapid 30 minute meeting. Revenue review, focus on what are blockers, what is getting in the way. Focus on owners, deadlines, next steps. No slides, no noise, no operational.

I used to call them my quick stand up. I taught my team the rule of three. They had to come in and in one minute or less give me three things about this deal that I needed to know and then end with, so it's a bottom line up front. Bluff is a military phrase, bottom line up front. Three things, one, two, three, and then conclude with here's what I know, here's what the so what is, or here's a call to action. People come in without slides.

and give you those updates, you're gonna see your pipeline tighten up. And you're not gonna have surprises, you're gonna have that transparency. And then every meeting must either build a skill or make a decision. How many times you sit in meetings and it's just updates and it's updates and there's nothing. Either we're going in to make a decision or we're gonna build a skill. And like I said, I would do a 30 minute meeting, that, teach me something in five minutes at the end.

KK Anderson (06:18)

Excuse. Excuse. Excuse. Yeah.

Cherilynn Castleman (06:27)

So everybody is learning something every week and I have teach me something AI. And again, if it rotates, know, KK is going to teach us her best AI tip this week. Mark's going to teach us next week and next week I'm going to teach them. Everybody's best practices and people are going to learn things so they can teach them.

Mark (06:39)

and

KK Anderson (06:42)

it.

Mark (06:43)

Great. So we all know boards and CFOs fund what they can measure. funding is a big part of ensuring that you really are able to build the type of capabilities you're looking for and keep those skill sets building. So what three numbers belong on a page one to prove that change is working? And what targets would you make

to ensure that you can be confident that the program, the leadership you're bringing to the table is gonna create the lift now, this quarter, not quarters from now.

Cherilynn Castleman (07:20)

So the three numbers that I would look at, one is cycle time with a warm sponsor versus one without. So if you're doing this right and you're leveraging AI, it's very simple. You just want to say, here's what our cycle time is with a warm sponsor. We're seeing a lift in this. Number two, executive meetings by stage. So when do the executives join and what stage are you at? And being able to track that.

and the win rate on multi-threaded deals. those are the three things. And what I think you're looking for is somewhere between a 10 and 20 percent quarter over quarter. That is proof that you are driving change.

KK Anderson (07:56)

Amen. That is proof. Okay, Sherlyn, we are gonna go to our favorite section of the podcast. We call it rapid fire. And Mark, I want you to kick us off so that we land on my favorite question on me. You go first.

Cherilynn Castleman (07:58)

at

Mark (08:07)

You got

it. I'll start the first one. What is the first product or service you have ever sold?

Cherilynn Castleman (08:15)

Mark, I've been in sales since before Girl Scout Cookies were 50 cents a box.

Mark (08:18)

my goodness. Excellent.

KK Anderson (08:19)

did you do, Roscoe

cookies?

Cherilynn Castleman (08:20)

Every girl's got cookies. And I mean, I was probably in the first grade. Okay? And yeah, I was in the first grade and my brother would pull the wagon and then there were no order forms. They just gave you cookies and you went and sold them. And I would stand there and I just would say, you know, they freeze well. What's your favorite ones? And oh, and if you tried this, this is, know, and I'm telling you, you put them away, you freeze them, you'll have them at Christmas. And I just up-sold and I was...

I a top salesperson and I just loved it. I was probably six years old.

KK Anderson (08:51)

That's amazing. Okay, who is one of your favorite sales or leadership voices that you like to follow?

Cherilynn Castleman (08:56)

So I have always followed who he was known as the client success guy and that was Bill Green, the former CEO of Accenture. He's just made such a change in the way I sold and Bill always said two things that stuck with me. One, if you criticize people, you raise their defensiveness. If you challenge people, you raise their game. And so that's why I coach and I challenge people.

And the other thing he said, Sherrilyn, three C's. Competence, be damn good at your job. Be great at what you do. Confidence, just have confidence, have courage. And the last one, which I repeated here, is give a damn. Care about your clients, care about your industry, care about your product. He said the three C's, well, that is what makes you a great leader. And so I've read and listened to everything that Bill has done.

Mark (09:48)

right on. So one practice you believe every sales manager should adopt this quarter or maybe even this week.

Cherilynn Castleman (09:56)

I say curiosity. AI lets you be curious. ⁓ I was read in a couple of places that they say curiosity is the KPI for 2026 for sales leaders. So I think if you're going to leverage AI and build your AI fluency, curiosity, curiosity, just keep asking questions. What can I do better? And also one of my favorite prompts is what did I miss? What could I have done better?

So even though you've done the prompt, you've done the analysis, stop and say, okay, what did I miss? What am I not thinking about? How can I do this better? So curiosity.

Mark (10:28)

So this may be one way that humanity is evolving a little bit, because they used to say curiosity killed the cat. And now it's not going that way anymore. And think about it, with AI, there's so much power in curiosity. So I really love that one. Thank you.

Cherilynn Castleman (10:39)

You know

Yes.

KK Anderson (10:46)

So good, okay, and my favorite question. Okay, Sherrilyn, what advice would you give to your 21-year-old self?

Cherilynn Castleman (10:52)

So I would tell myself to trust my voice, trust myself earlier. I would tell myself, if given a choice, Sherrilyn, always choose kindness over being right. And the final one is always, always have the courage, regardless of what anybody else says, just have the courage, have the kindness, and trust yourself.

Mark (11:13)

All right, well, I'm gonna close this up with, and I'm really interested in this one with all the great stuff we learned about you during this call, Sheryl Lynn. What is your favorite non-business book?

Cherilynn Castleman (11:24)

The Untethered Soul. I read it every year. It makes me pause. It makes me spend a little more time on my rug. It is about self-reflection and choosing love over fear. And I've been reading it every year. I don't know, probably since it came out. I'm a voracious reader, but that is one book that I read every year. I love The Untethered Soul.

Mark (11:28)

Wow.

And I love that idea of like reading something every year. I've never really, it's not like I haven't read books again, but the idea of having something that's so impactful and rereading it every year is really cool. Well, so.

KK Anderson (12:02)

Wait, when are

you going to release your book, Sherrilyn? Surely there's one coming.

Cherilynn Castleman (12:05)

Well, so I have a book. It was actually top of Amazon's best sellers for women. It's been recognized by Salesforce, actually one of the top 10 best sales books and link. You can go to post pandemic selling.com.

And that's, you'll find out it's also on Amazon. It talks about a lot of things we've talked about coming out of the pandemic, why we had to connect with people, why people need us to be authentic and us to be curious and how to connect with people. It's called Post-Pandemic. It's what's in the cards. Post-Pandemic Selling is the name of it. Again, you can get it at postpandemicselling.com. You can also find it on my LinkedIn page or

SherrilynCalfsman.com or just connect with me on LinkedIn.

KK Anderson (12:48)

You're right.

Mark (12:48)

Very cool.

Cherilynn Castleman (12:49)

Thank you.

Mark (12:49)

Well, Cherylin, thank you so much for taking the time with us. This was really a pleasure. And thank you to our amazing audience. I hope I remember that every single time. I don't know if I do, but we want to thank them as well, especially as we're moving in and through the holiday season. So again, Cherylin, thank you. KK, thanks to you as well.

Cherilynn Castleman (13:12)

Thank you, KK. Thank you, Mark. And thank you to your listeners and your audience.

KK Anderson (13:15)

Make sure to check the show notes and to catch Sherilyn's LinkedIn Lives. They're awesome. Almost every week. Okay. Thanks everybody.

Cherilynn Castleman (13:20)

Thank you, Kate.

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, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams.

Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy.

This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise.

What You’ll Learn:

• AI as a Daily Sales Discipline: How a simple 15 minute daily AI prep routine helps sellers develop POVs, anticipate change, and continuously improve.
• POV Development at Scale: A repeatable framework for triangulating industry, company, and persona insights using AI.
• Making AI Revenue Relevant: Why leaders should evaluate AI through insights, context, and business impact instead of activity metrics.
• Trust in the Age of AI Noise: How better questions and deeper listening create credibility when buyers are overwhelmed with automation.
• High Connection Discovery Questions: How to use AI to reframe discovery questions that trigger trust, openness, and buyer engagement.
• Prospecting Without Pitching: Why offering value through insights, case studies, and tools beats asking for meetings.
• Navigating Modern Buying Groups: How to adapt when new stakeholders like CFOs enter late-stage conversations.
• Financial Fluency for Sellers: Why precise numbers, not rounded estimates, matter when speaking with executive buyers.

Key Topics:

• AI fluency as a mindset, not a toolset
• Daily AI routines for sellers and managers
• POV creation using LinkedIn profiles, 10Ks, and industry analysis
• Relationship selling and the science of trust
• Discovery questions that increase buyer confidence
• Avoiding buyer defensiveness and ethical AI use
• Executive conversations and CFO expectations
• Financial storytelling with insight, context, and impact

Guest Spotlight: Cherilynn Castleman

Cherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops.

Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles.

Resources & Mentions:

• Course: Smart Tips Sales – Master Relationship Driven Selling via AI
• Book: Post-Pandemic Selling
• Research Reference: Dr. Jane Dutton on High Quality Connections
• Concepts: AI fluency, POV selling, high connection discovery, financial storytelling

🎧 Listen now and follow Selling the Cloud for more insights on modern sales leadership, AI-driven GTM strategy, and building trust at scale.

Mark (00:31)

to Selling the Cloud. Our guest today is Cheryl Lynn Castleman, an enterprise sales leader turned strategic coach and Harvard instructor as well. She helps teams become trusted advisors with practical AI fluency and relationship skills. She also builds accessible learning at scale as a new to me creator. Her course, Smart Tips, Sales,

Master Relationships Driven Selling Via AI is super highly rated and available versus a via Udemy business. Her programs focus on outcomes you can see on Monday morning. Better discovery, cleaner deal strategy, clear next steps. She has coached thousands of sellers and leaders, lifted promotion rates through hands-on coaching.

and built a large learning community through weekly live sessions and workshops. She teaches simple operating rhythms that free time for customer conversations rather than adding more dashboards. And she's on a mission to equip 1 million women in sales and leadership with the fluency, confidence and playbooks to thrive. Here are three topics we'll cover today. AI fluency as a daily mindset.

How to use AI to amplify strengths and turn prep into a repeatable routine that shows up every day in results. Relationship selling and the science of trust, the questions and behaviors that build credibility fast with modern buying groups, and leading as a CRO in a time of extremely rapid change. How to focus to team, communicate change, improve impact without adding any additional noise.

Sherlyn, we're so happy and proud to have you here. Welcome to Selling the Cloud.

Cherilynn Castleman (02:13)

Thank you, Mark. Thanks, KK. I'm thrilled to be here today.

Mark (02:16)

All right, we're gonna take you right into our first topic. And our first question is, you frame AI as an amplifier for what sellers already do well. If a CRO asks you to install AI fluency in 30 days, what would reps and managers need to do each day and each week? And what early results would you expect by say week four?

Cherilynn Castleman (02:38)

So first of all, I would start with a 15-minute AI prep session for every rep. I would have them spend 15 minutes asking AI, first of all, one, to develop a POV, a point of view, which I know we're going to talk about a little bit later, for each of their clients. It's something they can do very quickly to triangulate and develop their opinion, because as you know, state of sales reports from LinkedIn and Salesforce told us that 87 percent of

B2B buyers expect us to show up as trusted advisors, meaning we have to have a POV. So use AI to develop your POV. Second of all, spend five minutes using it to look around the corner. Where is my industry going? Where is my product going? Where is my company going? If you ask those questions every morning, you're going to get insights. And the final thing is, what can I do better? What can I, what am I missing? How can I, so for example, I'll say,

How can I be a better coach? How can I connect better with my audience? What is a new training insight I can try? What's a new engagement I can use on Zoom? I am every day getting better. They spend 15 minutes every day amplifying what they already do. They're going to accelerate deals. Number two, I would encourage managers to add to their weekly minutes, teach me something in five minutes. Have every rep teach something to the rest of the team.

once a week. That means by the end of four weeks your team has learned five AI insights. Over the course of a year they will learn 50 AI insights. And I had a client who was in the middle of the pack as a manager for a Fortune 100 fintech company and she became the number one sales manager of the year within six months just by doing that one exercise. That will free up

And what you will see is you will see about 30 minutes a day freed up from your reps. That 30 minutes, if you have 50 reps and they're doing about $100,000 per deal and they're doing one deal a month, if you take that math out, that will give you an additional $4.5 million in new revenue that and no additional headcount.

KK Anderson (04:44)

Wow, it's really fascinating when you put it that way and you break it into numbers.

Cherilynn Castleman (04:47)

Yeah, and that is one of the biggest takeaways, I think, that sales leaders and chief revenue officers can look at is when we first started using AI, people were talking about how to use it for email and how to ⁓ sound better. And what the most recent research is coming out is you have to ⁓ apply what I call ICB, insights, context, business impact. How is it driving revenue?

How is it saving you money? How is it increasing operational efficiency? How is it increasing your ROI? Those are the questions that leaders want to start asking every single week. This is what my reps are doing. How is that making me money, making me more money, or saving me

KK Anderson (05:28)

And it's interesting because you need the leaders, the L1s and the L2s asking AI those questions and using the data to get smarter. But the sellers as well, like you said, use it to look around the corner, research your competition, your customers. And we know and have known for a long time that our customers are much smarter when they get to us. They know more about our product than we probably do.

Cherilynn Castleman (05:48)

It used to be there were a ⁓ couple of months ago we had about 79 % usage today. B2B sellers are 98 % using AI. Customers are 100 % using AI. So your customers are using AI and 100 % they know your company, they know your competitors, they know your product. They probably have done more research than you have. So that's why you have to show up.

Mark (06:02)

Thank

Cherilynn Castleman (06:12)

with a POV, you have to connect with them, you have to build trust with them. People want to do business with people they know, like, and respect. Period. And we can leverage AI to do that.

KK Anderson (06:24)

And so where I was gonna go next was, I actually, I kind of thought people were getting over this idea that AI is cheating until I was in the car with my kids of all people. And one of my daughter's friends was like, AI is cheating, I can't believe AI, it's just not fair. And it's interesting, do you hear that still in your trainings and your classes that people feel like it's a cheat?

Cherilynn Castleman (06:47)

And with a lot of women, Harvard did it. There was an article that was recently said how AI is impacting women's career. And they discovered that women use AI in business 10 to 40 % less than men. And when they asked them what was the real reason, women said, because it's cheating. And so I tell people, just reframe it. I said, take what you already do well.

What is your superpower? What is the one thing that you're better at that AI will never replace? AI will never replace your authenticity, your ability to care, ⁓ your ability to connect with people and ask AI to help you elevate that, to amplify that. Take 15 minutes in the morning and say, I'm a great listener. How can I be better?

I ask great discovery questions. How can I do better? I'm meeting with this client. We don't seem to connect. How can I connect better with this type of client? My client's very analytical, very amiable, very expressive. A trick that I tell people is write a simple email and then ask AI, rewrite this for an analytic, rewrite this for an expressive, rewrite this for a driver, and rewrite this for an amiable. They're different as night and day. That alone will help you connect.

with your clients, just reframing that. Another example is if you go to LinkedIn, go to the three dots, and it says PDF this profile. PDF the profile, attach it to the AI tool that you're using, and say reframe this email specifically for this person. And it will say, they're very innovative. They're very amiable. They're very analytical. And it will reframe it. You will connect with them. That's the power of AI and connecting with people.

Mark (08:24)

All right, well, that's very cool. So please help us to make this a little more Monday ready. Let's say a rep has a discovery call this afternoon with a new account. Walk through the 15-minute AI assisted prep that produces in your mind the most useful point of view for the call and how you coach them. How do you coach them to bring that into the conversation? We've discussed a little bit

this here, but take us a little deeper if you would.

Cherilynn Castleman (08:51)

Absolutely. So what I always coach my clients to do is to triangulate your POV. It's something that AI, generative AI tool does so well. So first of all, research your client. Pull down their LinkedIn profile. If they're an executive, pull their bio and that's number one. So you want to triangulate. want three things, industry, company, person or persona. So if you can't find the person, do a persona.

Pull down several CFOs in that industry. Pull down, if they're a Gen Z, pull down Gen Zs in that industry in that job role. So the better you can micro-segment, if you can't do the person, do the persona. That's number one. Number two is company. My favorite company document for publicly traded companies is a 10K. The Form 10K, as your listeners know, I'm sure, comes from the Security Exchange Commission. You can get it on

the investors page of any publicly traded company, and the third one is an industry analysis. My favorite place to get it is Value Line. Value Line is free on every public library. If you work for a large enterprise company, they have this information for you. They have an industry analysis. They have company analysis. Pull it in and ask AI to triangulate this for you.

and it will pull the three together and develop a POV. And then you just say to somebody, Mark, if I said to you, I have an idea I want to run by you, what would you say? People say, yeah, nobody's going say no to an idea. And that's all it is is an idea. Even if you're wrong, you get credibility because you showed up with an idea. So show up with an idea. This takes 15 minutes. This used to be an eight-hour workshop that I did on how

Mark (10:15)

Yeah.

Cherilynn Castleman (10:31)

to research and how to read a 10K. Value Line has the ratios in there, so it can pull it and it has the ratios in there for three years. It will do a financial analysis POV, it will do an expressive one, any way that you want it. Fifteen minutes.

KK Anderson (10:46)

And then you take that information and you turn it into a value hypothesis for what outcomes your customer wants to achieve and what's going to get in the way and how you can help.

Cherilynn Castleman (10:54)

Yes.

Right. So if it's a first interview, those are the three things. If it's a second interview, I include the discovery document with it. And whether you are going into a meeting and saying, have an idea to run by you, and you're starting your meeting that way, or you're sending a follow-up email, or you're going into your solutioning, or you're doing a demo, it doesn't matter. You always want to show up with your opinion. I'm the trusted advisor. I have an opinion.

And that's what it is. And you could say, how does this land with you? Or this is what I'm discovering in the industry. How does this resonate with you? You're asking their opinion, but you're showing up with somewhere to start other than just with open-ended questions.

KK Anderson (11:35)

So let's, we could stay on this topic forever. Let's move on to the second topic though, relationship selling and the science of trust. And what's interesting is I was listening to a podcast just this morning about how, thanks to AI, right? And if you, I mean, you see it every day, you scroll LinkedIn and it's like emojis and dashes and it's just a bunch of chatty-bitty trash, noise. Let's call it noise. I wouldn't say all of it is trash, right?

And so, and people are used to seeing that now. And so it's like the trust continuum is getting longer than it used to be. Like it used to be, like if you had a really slick website, you know somebody dropped 10 grand to build a really slick website or way more than that, right? You you used to be, and now an AI tool can turn that on and you know, 30 seconds flat. And so it's harder for people out there to know who they can trust and what's real and what's not real. And so,

you teach that trust shows up in what we ask and in how we listen. you know, AI is making that harder. Like how, like, how do you balance that? Like how have you added that whole dynamic and that change into your teachings and your coaching?

Cherilynn Castleman (12:41)

So the first thing that I do is I ask my clients to pause for a second and tell me what is it about their client that they really care about. You have to give a damn about your client. There's no AI tool out there that's ever going to do that. And that's where you start. So if you really care about your client and you pause and say, what is it you care about? What is it that's important to them? And if you don't know, that's the first place you start, because that's what you have to start from.

is you have to care about your client and what's important to them. Once you care about them, you can craft discovery questions that are high connection questions. And for example, and AI can help you do this. again, it's a tool to amplify and elevate you. So Dr. Jane Dutton at the University of Michigan has done a lot of research on high quality connections, HCQ. If you go in and ask AI,

to reframe your discovery questions as high quality connection questions, what you're gonna do is you're gonna trigger what I like to call the love hormones. It is the oxytocin. It triggers the hormones that makes clients trust you, like you, want to do business with you. For example, I had a client who was in the financial services industry.

And she used to ask her clients, tell me about your insurance policies or your insurance that you have. you how you feel when somebody asks you that. Her second appointment rate was around 17%. When she asked AI to refrain that, the question was, what is it about insurance that scares you? Can you see that just that little switch there makes somebody connect with you? I have another client, she's a career coach, and she used to say, tell me where you want to be in three to five years.

And she was coaching women and AI suggested that she ask, when was the last time you cried at work? Because if you're a woman and you're going to look for a coach, it's probably because something is upsetting you to tears. And so you can ask little questions that just connect with people. have a client that she sells ⁓ data to, she sells data and

All of her clients are data scientists. And she said, Sherrilyn, data scientists don't have feelings. I can't ask you questions. And I said, hear me. Just for one week, let's just try it. She came back, and her clients now know her as a data therapist. Because she started asking them, what does it feel like when your company asks you to change the algorithm real quickly to come up with something? And this frustrates and angers, and they don't have the right data. And so her solution helps.

resolve this and she's like now all my clients want to start with how they feel every time we meet. So she connects with them. She was able to renew more accounts than she ever has just by starting asking those types of questions. ask better discovery questions. Two of my favorite ones are either first or finance. What was it like for your first podcast, KK? Can you remember your very first podcast?

KK Anderson (15:38)

Yeah, the instant emotions, instant

Cherilynn Castleman (15:39)

Okay,

you see the emotion, you see what happens? Versus telling me about what's it like to have a podcast as a first question. Or if I asked you, Mark, what was your finest podcast? So first and finest questions are great connections to connect with people. You can make these very technical, very financial, very industry specific, but an AI can help you do that.

KK Anderson (16:01)

And I know Mark's gonna jump in here, but I gotta ask one more question. That's brilliant, by the way. I absolutely love that, first and finest. What about in prospecting, when you're trying to get the meeting? How are you breaking through the AI noise and building trust?

Cherilynn Castleman (16:15)

So just bottom line, offer value, offer value. Offer case studies, offer assessments, offer checklists. People are doing research. People want knowledge. And so I say leverage social proof. AI, anybody can go out in AI and say, I am a great coach, or I am a great podcaster, or I'm a great ⁓ strategist. Use.

LinkedIn or whatever platform you use or emails or whatever, however you're doing your outbound to demonstrate that you can prove you do this. So offer social proof. Here's a case study where I helped a client like you do this. Here's a checklist that I use with my clients. Here's an assessment that you and your team might want to take. I have an AI assessment tool that I give out and I'm constantly saying, do you want to see where your team is for AI fluency? Take this AI fluency assessment. It is just a free tool.

Here's a handout on how to prompt like a pro. Give value. Once you give the value, then I always say, if you have more questions about this, jump on my calendar. People know how to book meetings today. You don't have to book them. You can wake up every day with new clients on your calendar by offering value and insights. I ended up with ⁓ a huge client from a major retailer who said,

KK Anderson (17:19)

Yeah.

Cherilynn Castleman (17:27)

She just, she used all my free resources for six months and finally she's like, okay, now we gotta bring Sherrilyn in.

And she just got on my calendar, so we want to hire you. It's just that quickly. so what it is. The trust is there. Here, give value, give value. Stop saying, hi, I read your post and let's have a meeting. never, don't ask for meetings. Just give value. And again, if you can't think of what to give away, AI can help you come up with tools, resources. You have case studies. I've got clients who've gotten job offers.

and ended up earning six figures more than they ever had just by posting case studies on LinkedIn. Here's what I did with a client anonymously. Here's what I did with the top 10 airline. Here's how I helped them and the percentage I helped them did the case study. And I had a woman, the chief revenue officer called her and said, I want you to come in and be my head of sales ⁓ and went around HR and didn't even look at a resume. It's like, whatever you did with that client, I want you to do that for us.

Because it's proof, it's a social proof, a lot helps you do that.

Mark (18:29)

Right on. Sherilyn, that's so you've taken us through some of the things that you want to say and things that add value to the full discussion early on. Let's talk a little bit about things that that you want to make sure you don't say or things that could actually trigger things like buyer defensiveness. And in general, like what two behaviors that do you see that

you know, that you can then do the lower that threat and increase that openness right away.

Cherilynn Castleman (19:01)

So one of things that I call is don't be cringy, okay? There's so much information out there. It is so easy to take someone's information and abuse it. Don't do that. Just treat people the way you want to be treated. So number one is don't be cringy. Don't take the data, don't share somebody's information. Be respectful, be kind if given a choice between

You know, right and kind, choose kindness, just always be kind. I always say a fool with a tool is still a fool. There are fools out there with AI. Just because you have AI doesn't mean that you have to abuse it. Be ethical, stop and think about does this make sense? Is this ethical? The other thing is you will know if you're not triggering the trust and the love hormones, you're triggering their amygdala. And what happens when you trigger their amygdala

is you see fight, flight, fawn, or freeze. If you're seeing any of those with your clients, they're fighting with you, they're arguing with you, they are freezing, they are not showing up, they are stalled, they are fawning. You ever ask a client a question and they sit there and they look at you? Well, they are fawning. just, you know, that's where they are. Or they just ghost you. Any of those say, okay, I've done this, it's time to stop, and AI is a great tool. I tell people,

open a Word document, dictate just in your own voice what happened and ask AI to help you analyze it and say, what did I do wrong? What could I have done better? What made my client freeze? And learn from it. Another thing I see is that you mentioned it. So people try to sound ⁓ more intelligent or more technical. And how do you feel when you're around people with pretense? How do you feel when you go to that Thanksgiving or holiday meal

and your in-laws or somebody has a girlfriend or boyfriend with them and they're just putting on airs. Everybody knows it. They can't stand it. Well, we don't want to do business with people like that. So the best way to be authentic and have your authentic voice come through is to just dictate. I use Word because it's not intimidating. I tell people just go into Word, hit the dictate and just dictate the email. Dictate the script. Dictate what you want to do and then drop it in. AI will use your words.

they will use your intonations and you will sound like who you are. So those are a couple ways to avoid triggering the amygdala and have somebody go into fight flight freezer form for you.

KK Anderson (21:27)

I'm a big follower of Rory Vadin. I don't know if you know him. He runs Brand Builders Group and he wrote the book, Take the Stairs. And he says, my gosh, I feel like I've been quoting this every day. He says that in today's age, your humanness is now your uniqueness because everything else is,

Cherilynn Castleman (21:34)

Okay?

KK Anderson (21:46)

AI generated, like you have to leverage your humanness as your uniqueness. That's, that authenticity is still, is now even more than ever, you know, paramount. So buying groups are larger, they're complex. Very often, in these times, leaders who used to have decision-making authority now have to get the CFO involved and, and, and they're.

Cherilynn Castleman (21:51)

Yeah.

It is.

KK Anderson (22:09)

more constrained than they've ever been. And so how are like, on this theme of building trust and authenticity and triggering the love hormones, I love that by the way, how do you do that when you've got like a buying group that's constantly changing? Like you're halfway through your sales process, you're on a, you have a meeting to negotiate or talk about terms of something and then next thing you know, boom, the CFO is there and you've never met him before. Like what are your kind of tips on that?

Cherilynn Castleman (22:36)

So a couple things. So first of all, I always ask at the beginning of any meeting, whoever's there, because like you said, buying committees are much larger. They used to be three to five people. Today they can be 12 to 18 people on a buying committee. Regardless of how large the buying committee is, at the very beginning, always go into the meeting asking each and every one, if you could get one thing out of this meeting, what do you want out of this meeting? Because...

That may change the direction of the meeting. So you don't want to guess where the CFO, the CFO could be there because they're looking for operational efficiency, cost savings. They could be there because they're looking to drive revenue. They could be looking to improve the pipeline. You don't know why they're there. And so ask, and so I always ask, even if there are 15 people in the room, I'll take 15 minutes and say, real quickly, what's one thing you want at this meeting? And I note those down. Now I have the direction of the meeting. That's number one. Number two.

Do your homework and do like I said, so do a POV for the chief marketing officer, do a POV for the CFO, do a POV so that you have those. So you're not changing the agenda, you're just changing the lens. And number three, executives want to talk about numbers. Develop your financial fluency. Understand what the key numbers are. Are they interested in what's driving revenue?

and be able to tell stories. And the stories, again, is the insight, what is the number, what does this number mean, and where is this number going? How will it impact us in the future? So is it the cost of acquisition? Is it the cost, is it the life, the cost, the client life cost of, you know, of maintaining the lifetime value of that client? So.

Know those numbers and be able to speak to them. And one other tip I always tell people when a CFO is in the room, take your numbers out three digits. Never say 50 million. Say 47.2 million. Know your numbers by three digits. CFOs will dismiss you if you round your numbers as a salesperson. So know your numbers. I'm sorry, what? Yeah, if you talk to CFOs, they'll tell you, I hate it when somebody says 15%.

KK Anderson (24:33)

That's a good tip.

So that's a good tip.

Cherilynn Castleman (24:42)

Because nothing is exactly 15%. It's 14.7 or 15.2. So know your numbers, know them out three digits, know your numbers and tell financial stories with them where you can talk about the insight from the numbers, the context, and what it means to the business. And be able and have a financial point of view in your back pocket so that you're just changing the lens, you're not changing your agenda.

Mark (25:07)

Well, you know, Cheryl Lynn, that is also it's like speaking with someone who's bilingual and, you know, speaking in the language that they may be struggle with the whole time and maybe touching it for a second. You know, CFOs, are they are bilingual. And one of the items is numbers. It has to be. So that makes a lot of sense.

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, Mark Roberge joins KK Anderson and Mark Petruzzi to go deeper into what happens after product market fit is achieved and why going too fast too early can quietly break a business.

Mark breaks down the transition from product market fit to go to market fit, explaining why these stages must be earned in sequence, not pursued in parallel. He outlines what real go to market readiness looks like, how to design a buyer centric sales system, and why retention and unit economics are the true signals of readiness to scale.

The discussion also tackles sales process design, hiring profiles by stage, and the common mistakes founders make when front loading headcount after a fundraise. Mark closes by sharing a disciplined pacing model for growth and why predictable scaling beats vanity growth every time.

What You’ll Learn:

• Why product market fit must be proven before optimizing go to market execution

• How retention serves as the strongest signal of long term product market fit

• What defines go to market fit beyond revenue growth alone

• The core components of a buyer centric go to market system

• How to build a sales process that mirrors the buyer journey

• The difference between discovery driven selling and pitch driven selling

• How sales hiring profiles should change across product market fit, go to market fit, and growth stages

• Why aggressive headcount expansion often leads to future layoffs

• How pacing hiring and spend creates predictable and durable growth

Key Topics:

• Product market fit versus go to market fit

• Retention as a leading indicator of success

• Founder selling and unscalable early motions

• Go to market system design

• Ideal customer profile and buyer journey alignment

• Discovery, qualification, and modern selling principles

• Sales hiring by company stage

• Scaling headcount responsibly

• Unit economics and growth pacing models

Guest Spotlight: Mark Roberge

Mark Roberge is the founding CRO of HubSpot, where he helped scale the company from zero to IPO. He is a Senior Lecturer at Harvard Business School, co-founder and managing partner at Stage 2 Capital, and author of the bestselling book The Sales Acceleration Formula. His latest book, The Science of Scaling, distills decades of research into a practical, stage specific roadmap for sustainable growth.

Resources & Mentions:

• Book: The Science of Scaling by Mark Roberge

• Book: The Sales Acceleration Formula

• Organization supported: McLean Hospital

• Opportunity to download the first chapter via Mark’s website

• Pre order The Science of Scaling with proceeds supporting mental health research

🎧 Listen now and follow Selling the Cloud for more insights on building durable go to market engines and scaling the right way.

Mark (00:31)

I do wanna go deeper into the topic three here, go to market fit. Before I do that, Mark, is there anything you definitely just wanna cover?

in addition to what we did already on product market fit. If not, I've got another question for you.

Mark Roberge (00:44)

Not at all. Like so far we have is like, you need to try product market fit first. We're quantifying that as retention in the long term and defining a lead indicator retention in the short term. And we created a framework for that. And the famous Paul Graham says, the founder of Y Combinator says, do unscalable things early. We're not worried about a scalable demand gen channel, a scalable sales process. We're doing founder selling. I don't even need to optimize price at this point. And I prefer to pay my salespeople with equity and not industry commission. Let's just get to success.

KK Anderson (01:06)

I mean, stop it.

Mark Roberge (01:12)

Once we have that, we move to go to market fit. We can't do them at the same time because you risk optimizing the go to market on the run market. If you don't prove product market fit first, but we moved to go to market fit and that just tells us that we can create this value profitably as measured by unit economics. And this is the stage where optimal quota price, demand, gen channel and sales process come into play. That's where we're at right now.

Mark (01:32)

Yeah, right on. Okay, topic three. So go to MarketFit. We want to go deeper into the process, the hiring, the demand, the pricing side, the compensation side. This is where I think a company gets to run and increase their productivity the fastest of any other stage. So you define go to MarketFit as generating customer success and revenue consistently and profitably.

Starting with process, so starting with process, what should a codified repeatable sales process include at this stage? And where is the line between useful structure and a little bit of bureaucracy that slows deals at the end of the day?

Mark Roberge (02:12)

yeah, sure.

Okay. Framing out one step. talk for a decade now around the go-to-market system design. This is what we teach at Harvard Business School. And so trying to move away from sales is just an art form. Let's give our salespeople a bunch of leads and let them do what they do best and go close business. Now, like we have a system for our finances. We have a system for our product development. We need a system for our go-to-market. So we call this go-to-market system design.

The go-to-market system sits on top of obviously your first target market, your ICP, ideal customer profile. On top of that is a definition of how those buyers buy, the buyer journey. And on top of that is your sales process, which just helps them buy. There's two inputs to the system, the salespeople you hire and the demand that you create. And then the system runs by how you coach and pay them. And it spits out in sequence, sales activities like meetings and demos that lead to

a forecast that lead to revenue. That's the system. And so within that system, Mark is a process. So it depends where you're like, at the very bottom is the ideal customer profile, which we can talk about. It's just really who we've proven to be able to sell successfully and make them successful. And so I mentioned like on top of that is a buyer journey. This is a part that's often skipped in sales process development. I think founders think that their sales process is a pitch deck.

think like a good meeting is like, I went to the meeting and I got through all 27 of my slides about the problem I'm solving and how my product works and the awesome case studies we have. It went great. And there's a million studies that we know that shows that that is suboptimal selling. I can't find a study that says it's good. We know that in the first meeting, the less that the seller the better. And so what's happening in there is

You're qualifying and discovering. You're discovering what the buyer perceives as their biggest problems and how they're thinking about it before you tell them about your product. And you're qualifying to see if you can make them successful, if they're in a position to buy your product and be successful with it. That's our objective. And we can't do that unless we understand a buyer journey. So the buyer journey is really just like sequentially how the buyer comes to terms with purchasing your product.

They don't wake up one day and be like, where's that contract? need to buy that product. They wake up one day saying, I have a major problem. And that's their first stage is it's just like the awareness stage is like, is this a problem? Is it a big problem? Yeah, it is a big problem. Why is it a big problem? How do I think about this problem? How do I frame this problem? Then they start considering solutions. how do I fix this problem? Do I delegate it to someone on my team? Do I hire a consulting company?

Do I buy a software product? And then once they've decided how they're going to solve it, they choose a solution. I'm going to delegate it to Mary. I'm going to hire a seller in the cloud. I'm going to like, you know, I'm going to buy this software product. Right? So like, no matter what you do as a seller, that's what they're going to do. So if we understand that and frame it in that way, and we look at our sales process, not as going out and

Mark (04:45)

Thank

Mark Roberge (05:01)

pitching the world on everything we've built. But instead going out and discovering how people are perceiving this problem and qualifying whether we can help them and help them make a good purchase, that's modern selling. That's buyer-centric selling. with that in mind, the components of your sales process is your ICP definition, it's your buyer journey, and then it's how you take that, how do you run that first meeting, which is often called the discovery guide.

And then once you've done your discovery and qualification, whether that's in five minutes or five meetings, you usually move on to some sort of a presentation process on how you explain how we're a fit. ⁓ then once we're, you know, hopefully the outcome of that is a purchase and we get to a onboarding and customer realization process. like, you know, obviously within there is negotiating contracts. It's like, there's a lot of different steps, but those are generally the components of the sales methodology.

KK Anderson (05:52)

You are preaching from the AGS playbook the framework that we talk about a lot at AGS, we call it the two sale mentality, which is taking, I feel like I say this every single day actually, whether you're selling Girl Scout cookies or you're selling multimillion dollar software.

Mark Roberge (05:56)

Yes, exactly. KK. I figured.

Mark (05:57)

⁓

KK Anderson (06:12)

every sale is really like two distinct sales. And the first one is getting the customer to articulate why they need to change. And it has nothing to do with what you're trying to sell. It is why, this is a problem, why is it expensive? why getting that and getting them to say it right. And the second sale is why you and why now. And, and one of the things that we do a lot of our competency assessments where we'll, we'll take a sales team and we'll give them,

the assessment we use objective management group, and we'll be able to see that they're really low on that discovery, those competencies on the discovery end. And then the second sale, they're like aces. They're selling value is like 80%. They're really good at presentation approach. Like they're really good at selling the second sale. And that is like the immediate recognition of, my goodness, you know, our sales process is not matching our buyers journey.

Mark Roberge (06:48)

Yeah.

Yes.

KK Anderson (07:02)

And that's, that's, love everything you just said there. So go ahead.

Mark Roberge (07:05)

KK. I mean, to your point, it's like you have to meet the seller where you are and that's what you all preach. It's just like, okay, we're selling Girl Scout cookies. Like, where are they at right now? Like, thing is like, are they even hungry or not? Like, if they're hungry, I'm gonna pitch them in a different way. I'm like, did you already have...

KK Anderson (07:18)

you

Mark Roberge (07:24)

Lunch? Yes, I did. Would you like a treat then? Yes. Now I just have convince them that my Girl Scout cookie is better than the candy corn or the dark chocolate. It's a very different pitch versus if they're not even hungry, I can still sell them a box, but my pitch is different because it's like, are you going to be hungry later? And would you like to support a co- like, you know, it's just, it's a very different perception I'm leaning into. So, but like, you know, many founders come out of the gate. I've never sold before.

and they just think this is about getting through the 27 slides.

Mark (07:52)

Yeah. And Mark, though, the one problem with that is that being hungry has nothing to do with when I eat a Girl Scout cookie. It just pretty much is when it's accessible and then I just start eating them. So complicating fact for our sellers.

Mark Roberge (08:00)

Yes.

Right. Just looks really good.

KK Anderson (08:06)

So I have a quick question though before we keep going. This has just been so fascinating. So let's say you're in go-to-market fit, you've got your go-to-market system down. What are you looking for in those first five A's that you're hiring? How do you know you're gonna get someone that can sell to their sales process?

Mark Roberge (08:28)

And you're raising up another, I think important abstract point that we take away here, KK, which is at this point, we've got a clear definition of how we move through the readiness to scale from product market fit to go to market fit. eventually we get into the growth stage. What we haven't covered yet, and we have also discussed the go-to-market system, that this isn't an art form, just like we have a finance system and a product development system, we have a go-to-market system.

And we've talked about the components of those, you know, our ideal customer profile, sales methodology, our sales hiring, our demand gen strategy, and KK is asking about the sales hiring component. Now what we haven't talked about this important point, which is the optimal design of those components is contextual. have discussed that a little bit. Like don't...

Don't be bringing like an AI cyber product to market in 2025 and copy what HubSpot did in 2010, bringing a marketing product to small businesses. Like these optimal designs are contextual to the product you're selling, the buyer who's buying, and nuances of your own business in terms of stage and culture and all that kind of stuff. But another contextual driver is what stage we're in. Product, market, fit, go to market, fit, growth and moat. For each thing.

including KK's question of the odd deal sales hire. I will tell you, if you are bringing a new product to market and you're in the product market fit phase, the absolute worst hire you can make is the number one salesperson at workday right now. The number one salesperson at workday is a genius. They are like the Michael Jordan of sales. They make millions of dollars a year.

and they will destroy your company if you hire them during the product market fit phase. Because like when they joined Workday, they went through a month of training with all the objections, the entire playbook. Their manager was there coaching them through. You don't have any of that. You don't even know if you have the right product. Right, so like.

The optimal hire at the product market fit phase is kind of like half account executive, meaning they can talk about commercials and do a little discovery and all that kind of stuff, but half product manager who can like reflect on the 10 conversations they had with the market this week, summarize the patterns and talk to engineers about them. That's what we need. When we move to go to market fit, which is specifically where KK is asking is, okay, we feel like we've got product market fit now.

Now we need to build the process. So we need a couple salespeople probably, and one of them has to be really good at sales methodology development, which the number one rep at Workday has no clue how to do. Okay, so we need a process builder. And then finally, when we get on the growth phase, that's when we got the number one rep from Workday come in. If they're the right hire, again, like the optimal hire for Workday is probably different than the optimal hire for us. But at this point, it's more of as if I can quote the sales learning curve, a coin operated salesperson.

that's going to take the pitch deck, it's going to take the comp plan and it's going to sign up a bunch of healthy customers for our business.

Mark (11:16)

Excellent. Okay, so let's move into our final topic here, growth and mode. So when teams set the growth and mode stage, you warn against front loading, hiring and pushing vanity growth. What pacing model do you like for headcount and program spend and which board level guardrails keep an honest quarter to quarter? And I'd like to really take this deep, just kind of...

Mark Roberge (11:24)

Mmm.

Mark (11:39)

reminding myself even how brilliant our audience is and how this is an area that they don't often get guidance on because most of these, whether it's podcasts or things that are written for sales leaders, doesn't go into the level of just execution and structure that I'd love for you to go into in the few minutes we have left here.

Mark Roberge (12:03)

and

yeah, just to frame it, I every quarter I run into this story.

You know, whether the company is at like a million trying to go to 10 or if they're at 10 trying to go to 100 or whatever.

it's like, just had this one happen. Some founder was pitching me and they're like, yeah, we'd love to raise around and we're gonna go from 1 million to 6 million this year. And that's possible without headcount with like a PLG type distribution, but this wasn't a PLG distribution. I was like, how are you gonna do that? And they're like, well, we hired 15 salespeople last month.

And I was like, How many salespeople did you have three months ago? And they said one.

And I was like.

They're like, what's wrong? I'm like, you're going to lay off 12 salespeople in like eight months. And that's just what I know why it happens. I know exactly why. Well, first off, why does this break? Okay, this breaks because you're just not ready to hire, ramp and enable that many salespeople that fast.

Mark (12:47)

without question.

Mark Roberge (13:00)

And there's no appreciation of what that takes. Let's just start with the recruiting muscle. Like I, let's, I don't have like raw data on this, but I know that if you are, generating for each hire sales hire, if you generate 40 candidates and screen 20 and interview 10 and hire one, that hire is going to be better than if you generated one candidate screened one person.

interviewed one person and hired one person. It just is. And you just don't have the recruiting muscle to even attract that high of a quality talent bar and interview them. Nevermind you don't have the demand gen formula on how they're going to get meetings. And you also don't have a proven process and you don't have a management layer. Cause the average manager ratio right now

For outside is six to one and for inside it's like eight to one that will probably change with AI, but we're not there yet. So there's just all these like very obvious reasons why this is going to fail. and so I know why they do it. It's just that they promised their VCs this massive valuation and the VCs bought it. So now they promised this massive growth rate and they just opened up Excel or a Google sheet and divided by the expected revenue divided by.

the quotas and that's the number of reps they have to hire next month. And that's what they think of scale pattern is. And so let's go get more leads. So we triple the burn now. So anyway, the easy fix in our final two minutes here is don't think about scale at that point as a one-time event at the beginning of the year or after a fundraise and then absorption over the year of those reps. Think about it as a pace.

KK Anderson (14:14)

And that's why the CROs are saying, get us more leads.

Mark Roberge (14:34)

So don't think of it as like we're gonna hire 15 reps in January of 2026 and cross our fingers and try to hit our number. Think about it as we're gonna hire three reps a quarter.

And so like, let me just, to finish it real quick is there's gonna be signals every month and every quarter that will tell us if we're going too fast or too slow. It's really the leading indicators of retention and the leading indicators of unit economics. And so if we make those three reps and we go through the ramp and like, we look at this two quarters later and it's like, wow, things are good. Then we go to six reps a quarter.

And then it's like, if it breaks, we'll fix it. We'll know a way ahead of everyone else and we'll fix it. It might take a week. It may take a month. It may take a quarter, but we'll fix it. And then we'll go to 12 reps a quarter. And then we'll go to 20 reps a quarter. And then we're a unicorn. And we did it in a very predictable way.

KK Anderson (15:18)

That sounds amazing and like a strong game plan. If only it were that easy, right Mark? Real quick before we wrap up, I love that you're donating 100 % of the proceeds from this book to McLean Hospital. Why is that important to you? Tell us a little bit about.

Mark Roberge (15:24)

Exactly.

Yeah, I just think like I don't know the last proceeds to an awesome for sales acceleration form at bill.org. That's another really big motivator for me writing a book. You know, you never want to do badness with tech. We always want to make the society better. never want to see that's that's the cause right there. That was awesome. So you never want to. Nice. I love it. I'm feeling the joy.

Mark (15:49)

got to ⁓

KK Anderson (15:51)

Yeah,

that's my senior finishing his final.

Mark Roberge (15:58)

You never

want to do badness with tech. I think like mental health has been a little bit of a negative ramification as we've gone through various variations and I've suffered dramatically myself. I've had severe anxiety and there's a stigma out there in the world around mental health. If you find out that a candidate is a cancer survivor, a job candidate, I think that elevates your perception of them. If you felt like they had

severe depression and we're hospitalized for it, you have concerns and that's not right. They're both diseases. I've had that and I've been fortunate to be blessed with things that people perceive as successful so I can speak openly about this without massive concern. We're getting better with each generation ⁓ but we need to do even more and I think McLean is the global leader around that.

In addition to helping with your skill pattern, just know that you're also helping with the great societal cause as well.

KK Anderson (16:50)

Well, that is incredible. And so the Science of Scaling is available for pre-order now. It releases on February 2nd. And Mark, if it's okay with you, we will leave a link in our show notes to where they can go to your website and they can download the first chapter. will get you there.

Mark Roberge (17:01)

Great.

I'd love

Mark (17:04)

Yeah, and we should also include

a link to just the donations at McLean. So we will add that as well.

Mark Roberge (17:11)

Yeah, and you can pre-order the book now if you want to do it that way. That'd be helpful. But thank you, Mark. Thank you, KK. It's an amazing platform to be a part of.

KK Anderson (17:19)

Thank you so much.

Mark (17:19)

Pleasure, thank

you as well, Mark.

Mark Roberge (17:21)

All right.

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