Tom Wentworth (CMO @ incident.io) is replacing himself with an AI CMO.

It's scary good.

He came on my podcast to talk about how he's actually using AI in marketing, and:

* Why he moved from 'big company CMO' to a scrappy team of 5.

* How they're using AI to drive pipeline right now.

* How to build a culture of AI adoption.

* His formula: Marketing Output = AI × Taste²

* Where the AI puck is going.

* And of course, how he's replacing himself with his Claude Code AI CMO.

My takeaways from our talk:

1️⃣ Make AI a team sport

Tom is leading from the front. In the tools daily testing, learning, shipping. He's aproaching AI as a team sport. No one is solely responsilbe for 'AI Adoption'. Everyone is experimenting, and everyone is benefiting.

2️⃣ Marketing Output = AI × Taste²

"Taste is an exponential contributor to marketing output and it can't be easily automated". The place most people fail isn't in the ability to write or build *something* it's to write or build the right thing, that they're be proud to ship.

3️⃣ AI Marketing can be wonderfully compounding

Claude Code will keep getting better --> his 'context database' will keep getting better --> his agents will work better --> they'll invest even more. His AI machine is compounding. Everything it makes, makes the next thing easier to do, faster, and better.

4️⃣ It's still early

Tom talked about how he'll talk to some marketers who work at companies who aren't explicitly pro-AI usage. His advice to marketers at these companies: leave. It was surprising to me that some companies are still not bought in, but it makes sense. We're still early.

Full episode here: https://www.peersignal.org/podcast

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

Udi Ledergor was employee #13 at Gong and the first marketer.

He's a legendary CMO.

Not only did he help build one of the most impressive businesses in SaaS, he built one of the most impressive teams.

People like Russel Banzon (now CMO @ Cresta), Chris Orlob, Devin Reed, Sheena Badani came out of his talent factory.

He came on my podcast to talk about:

* Best practices marketing vs. corageous marketing.

* How to keep boldness in the culture as your team grows.

* Why "different is better than better".

* Why "story-audience fit" matters more than storytelling skills and how to test it properly.

* How AI and modern tools can amplify courageous marketing strategy (but never replace it).

And more.

My favorite takeaways:

1️⃣ "Different is better than better" (and better than boring 'best practices')

By the time something becomes a "best practice," everyone is doing it. If you want extraordinary results, you have to break away. It's risky, but not as risky as getting lost is the sea of sameness.

2️⃣ Simple marketing measurement trumps fancy attribution.

You don't need complex attribution to prove if something works. If it really works, you'll feel it. And if something flops, you'll feel that too. Focusing on clear signals rather than trying to track every micro-conversion frees marketers up to take bigger swings.

3️⃣ Subject matter experts can be your best marketers

Legendary marketers like Chris Orlob or Devin Reed weren't legendary marketers when Udi hired them. They just knew their persona cold. I think this will continue to prove a competitive advantage as AI enables anyone to create AI slop content.

4️⃣ Every touchpoint is a brand moment

From privacy policy emails to webinar invitations, every customer interaction shapes perception. Treat the smallest details as opportunities to reinforce your differentiated brand experience.

5️⃣ ICP Discipline is a competitive advantage

Amit, their CEO would consistently say no to short-term revenue in the early days because he knew it would distract, drain, and diffuse focus. Easy to say, hard to do, but so valuable if you can maintain that focus.

This was one of my favorite episodes.

If you want to learn more from Udi, I can't recommend his book enough. It's a must-read for any marketer looking to level up.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

Kipp Bodnar, HubSpot's CMO (scaled marketing from startup to $30B leader), told me something uncomfortable for marketers:

"The types of metrics that people cared about a couple years ago are far less relevant today than they have ever been."

Marketing math is getting rewritten with AI. And Kipp says it's the most fun he's had in the last decade. He was my guest for episode 9 of the PeerSignal.org podcast.

What we covered:

* Why he's 10X more productive than pre-AI (with details).

* His "Express, Feedback, Tailor, Amplify" framework for AI campaigns.

* How they increased email engagement 100-400% with AI personalization.

* How he gets his 600-person team obsessed with AI.

* Where smart CMOs are investing or cutting back.

* Why "taste at scale" will separate winners from losers.

And so much more.

My favorite takeaways:

1️⃣ Better, faster, AND cheaper isn't a trade-off anymore.

When someone brings Kipp an idea, he asks: "Is it better, faster, AND cheaper?" If not, he won't do it. Most marketers still think you have to pick two. They're wrong.

2️⃣ AI isn't just automation, it's creative leverage.

AI models are trained on everything that's already been created. If you're still running campaigns the same way you did 2 years ago, you're already behind. He wants humans who can create with AI.

3️⃣ Taste is the new competitive advantage.

"As much as I want you to learn AI, I want you to learn how to have good taste." Most marketers think prompting is the hard part. They're wrong. The hard part is knowing good from garbage.

4️⃣ We're still early in the AI wave.

Search engines were around for years before SEO was born. Hubspot built a movement on top of this years later. ChatGPT launched 2 years ago. We're still very, very early (as easy it is to feel behind).

Here's the uncomfortable truth most marketing leaders won't admit:

The internet is littered with people selling "copy my exact system to become AI-native." Reality: There's no playbook, no experts. This is all being figured out in real time.

People like Kipp are curious learning machines. They try a lot. They find leverage in surprising places. They push and pull constantly. These are the people to study.

What's your take. Does Kipp's thesis on AI + marketing track for you? Or does this sound like hype?

Let me know in the comments.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

Manny Medina built Outreach from $0 to $4B+.

He created the sales engagement category by riding the SaaS wave from 2014 - 2024.

Now he's on the cutting edge of a new wave: The Agent Economy.

While most of us are in the fog of AI war, Manny has inspiring clarity on what this new world will look like, why, and how to win in it.

That’s what we cover in this episode. If you care about winning with AI, it's a must-listen.

What you'll learn in our conversation:

* How to compete when every feature can be copied by AI in minutes

* The "one box" revolution and what it means for AI

* The "rent experience, hire hunger" framework for agent-era teams

* Why agents need to think, suggest, and act (not just automate)

* How the best leaders will adapt to this new paradigm

* How to demo right in the agent economy (not just slapping AI on your homepage)

My take-aways from our talk:

1️⃣ We're in software's 3rd Act, Outcomes.

Act 1: Systems of record. Act 2: Workflows. Act 3: Outcomes. In this new world, you need to deliver "receipts not dashboards". This has ramifications throughout your org structure.

2️⃣ "Love is not a metric".

Love is not a metric. It's a feeling. It's the words they use. It's when an SDR tells you, "you'll have to pry Outreach out of my cold, dead, hands." The best leaders optimize for love and don't stop until they get there.

3️⃣ "If you're worried about TAM, you haven't found your edge yet"

Every leader has a choice: sell to everyone, and be relevant to no one, or take a stand and actually break through. In this 3rd wave, the winners will be the leaders courageous enough to take a stand and be truly different, even if there's no "TAM" to back it up.

4️⃣ Build backwards from customer success, not forward from features

"What does the customer want? They want a meeting in the least amount of time. They don't want 12 steps. They want one step. Matter of fact, they want zero steps." Winners don't retrofit the human to the technology. They start with the outcome, and work backwards.

Full Interview: https://www.peersignal.org/podcast

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

This podcast is sponsored by Keyplay. Check out their new AI Agents for ICP Targeting. You can use them to answer any question about every account in your market and find ICP accounts that your competitors are missing.

If you're a marketing leader, you should be studying Kyle Lacy's career.

* Pioneered content marketing in B2B at ExactTarget (acq. for $2.5B by Salesforce)

* Scaled Lessonly's marketing team from 7-80 people.

* Drove 20X revenue growth with marketing consistently sourcing 70%+ of revenue.

* Now CMO at a publicly traded company (Docebo, $1.1B market cap)

* And most importantly. When most CMOs last <18months, he hasn't been fired once.

He came on my podcast and shared the lessons he wish he'd learned at the start of his 17 year career. We covered:

* Why ABM doesn't work (and how to fix it)

* Sales, marketing & CFO alignment advice that isn't "just have a weekly pipeline meeting".

* Elevating marketing to a strategic partner, not an order taker.

* 'Surpsise and Delight' in practice.

* How he builds 'high horspower' marketing teams.

* How he got to CMO before 35.

* Pipeline modeling for dummies (and smarties).

* Avoiding burnout as a leader and a dad.

and more.

My favorite takeaways:

1️⃣ Why ABM Doesn't Work (and How to Fix It)

ABM fails because marketers overcomplicate it with technology and processes. Kyle's Fix:

* Start small with 20 accounts, not 5,000. Get sales leadership involved in account selection from day one ("don't come with the answer, ask the question").

* Build a test with clear success metrics ($15-20 of pipeline per dollar spent), prove it works, then scale.

* Focus on helping AEs hit quota capacity, not just generating stage one pipeline. Use a combination of air cover (ads, content) and human outreach (BDRs, AEs doing prospecting).

2️⃣ How to Get Sales, Marketing & CFO Alignment

The CFO sees sales and marketing as one line item against blended CAC. When they have $100K to spend, it should be a joint conversation between sales and marketing leaders about where that money goes - not a fight for separate budgets & who gets credit.

So, as a marketing leader, you should know how AEs are doing, where pipeline stands, and what the sales forecast looks like. Misalignment shows up when marketing celebrates brand campaigns while missing bookings targets.

3️⃣ 30% Rule to Balance Brand & Demand

It's easy to get sucked into predictable demand investments. Especially with pressure from above. But this hurts you in the long term. Kyle always makes sure to allocate at least 30% of his spend to creative, illogical bets that won't have clear ROI. Surprise & delight direct mail is a great place for this spend to go.

4️⃣ Building High Horsepower Marketing Teams

Kyle doesn't choose between doers and managers on his teams; he looks for both. High-horsepower practitioners who can set a sharp strategy and are excited to execute. You'll get better results, and it'll be more fun.

Thanks so much for listening!Have any guests you’d like me to interview for future episodes?Let me know, I read all the replies :)

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

“Sales is hard again… Good.”

That’s what Josh Allen (ex-CRO of Drift, Owl Labs, VP Sales CarGurus) told me on this week's episode of the PeerSignal podcast.

We talked about what WON’T change in GTM. His sales fundamentals and insights learned from 20+ years as one of the best CROs in the industry, and how he's applying them as CRO at Quickbase.

What we covered:

* His "sales math" framework for predictable revenue growth.

* The outbound that actually works (still).

* How to build a culture where salespeople control their own destiny.

* The special trait to look for in the very best reps.

* Why sales enablement leaders MUST have carried a quota.

* How running ultra-marathons shapes his leadership approach.

We covered a lot of the "simple but not easy" practices that separate the best sales leaders from the rest.

1️⃣ Sales Math

Josh shared his "Sales Math" framework. Proving, with real data, how a rep will hit their number should be every CRO's #1 goal. Proof begets belief which begets results. Without it, reps don't put in full effort because they never believed they could hit their number in the first place. This is how Josh gets more out of every rep and builds a culture of real accountability.

2️⃣ CarGurus $900M ICP Framework

Josh shared how the best teams map TAM, SAM, & ICP. We talked about what good looks like. How, at CarGurus their ICP was so clear "that we never even had to talk about it" and how that clarity propelled them from $198m to $454m in revenue in the 2 years he was there.

3️⃣ Intensity + Focus = Outbound Success (this still works)

Josh shared his playbook for building an outbound culture that actually drives results; intensity & focus. Focus, on the right plays to the right accounts, and intensity in how they execute those plays.

4️⃣ How to win when "Sales is hard again"

"There's a group of sales people who leave the workforce in technology and never come back." Sales is hard again. Josh has been through hard times before and shared how he responds quickly and decisively. From how he builds teams who actually enjoy, and thrive, in this new environment, to how he re-works revenue forecasts to reflect the new reality.

This episode was one of my favorites. It's one I'll continue to come back to as the work evolves.

What did you think? Would love any feedback or guest ideas! Just reply to this email, I read them all.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

This podcast is sponsored by Keyplay. Check out their new AI Agents for ICP Targeting. You can use them to answer any question about every account in your market and find ICP accounts that your competitors are missing.

Heidi Bullock has been the CMO of Tealium for the last 5+ years (Engagio & Marketo before that). She's widely regarded as one of the top CMOs in SaaS.

I wanted to learn how she got to be so good, and what GTM Excellence looks like on the inside for Tealium.

That’s what we cover in today’s episode of the PeerSignal Podcast.

What you'll learn in our conversation:

* The three non-negotiable fundamentals of effective ABM.

* Why Tealium focuses on regulated industries despite initial success elsewhere.

* Why your ICP strategy is probably wrong (and how to fix it).

* How to get "story-audience fit" and why it matters more than most tactics.

* How AI is transforming her marketing operations.

* Her daily mantra for maintaining calm in high-pressure marketing roles.

My take-aways from our talk:

1️⃣ Story-audience fit trumps storytelling

Even brilliant stories fail when they don't resonate with your specific audience. Heidi tests every narrative with actual buyers, not just colleagues who'll praise anything. This is why many B2B brands invest heavily in storytelling but still sound generic - they create stories they love rather than stories their customers connect with.

2️⃣ ABM requires the entire revenue team

The reason ABM is hard is the same reason it works - it requires true alignment across marketing, sales, and customer success. Everyone needs to understand what you're trying to do and their role in the game. Heidi some resources that helps operationalize this.

3️⃣ Make your customer the hero

At Marketo, they realized marketers weren't seen as revenue drivers. Instead of being "just another marketing automation tool" they built a movement where they elevated the entire job. The best B2B brands don't just solve problems - they tap into emotion and identity. They make customers feel seen, understood, and empowered. They make them a hero.

4️⃣ Win credibility with ICP

Heidi shared how strategic she is about ICP. Looking deep at retention by segment and bringing that data forward into their ICP Modeling & Account Selection. This is foundational to her results, but also her success in the board room. Every modern CMO should be proving ICP with value & business metrics first, and marketing metrics second.

Thanks so much for listening! Have any guests you’d like me to interview for future episodes? Let me know, I read all the replies :)

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

Going upmarket is always attractive, but never easy.

Jeff Wharton is doing it right.

He walked me through his approach, moving from 100% inbound to landing logos like 7-eleven, MGM, Cisco, and Shake Shack.

This interview is a perfect ICP Marketing story.

Jeff went deep on the specific challenges LogRocket faced in their trek upmarket and how he overcame them (with lots of details).

What you'll learn in our conversation:

* How he turned a failed 'donut campaign' into a machine that consistently penetrates 25% of target accounts.

* Why they treat their SDR engine as a "product with modules".

* The art of knowing when to abandon vs. optimize marketing tactics.

* How they use AI throughout their GTM.

* Why they strive to be "data-guided" not "data-driven" marketers.

* How to use true value delivery as a way to differentiate your GTM.

Oh, and the surprising importance of phonetic pronunciation guides in enterprise outreach.

My takeaways from our talk:

1️⃣ "Treat your go-to-market motion as a product"

Jeff approaches his enterprise SDR engine as "a product that we're building in the marketing team." Each growth initiative is focused and accountable to specific metrics within the system. There are so many breakthroughs us marketers can steal from product people. This is one of them.

2️⃣ "Know when to kill vs. optimize"

We all struggle with knowing when to pivot vs. persevere. Jeff shared a helpful frame: "Was the original idea a flyer, or did we think about it from a very nuanced perspective?" and "Do we have at least one anecdotal proof point?" if we do, sometimes one more crank of the wheel is all it takes to get it to work. If not, we need to be "unemotional about stopping things."

3️⃣ Enterprise and PLG isn't "or" it's "and"

"If you build a product that is intuitive enough that credit card swipe customers can continue to use it really well and find value, it's gonna be easy for enterprise customers to use too." It doesn't need to be PLG or enterprise. These motions can be mutually beneficial.

4️⃣ It's not the channels, it's you

For all the talk about dead channels, it was good to hear what's working for Jeff. Specifically, LinkedIn Ads. He shared how they segment, retarget, and bid intelligently. For anyone, it's a good reminder that it might not be the channel that's broken; it's the way you're executing inside of it.

This episode is the third of my new PeerSignal podcast series where I'm interviewing go-to-market leaders on what works and the principles behind them.

Full Interview:

https://www.peersignal.org/podcast

Would love to hear from you!What did you think of this episode? Who do you want to learn from? What else do you want us to dive deep on?Reply to this email, I read every one :)

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

TalkDesk ($10B+), Gong ($7.25B+), and Cresta ($1.6B+) had a secret weapon.

Russell Banzon.

As CMO at Cresta (an AI unicorn), he's building an enterprise marketing machine that's powering incredible growth in a competitive market. And it’s built on a foundation of learnings he acquired at some of the most effective marketing organizations in tech.

He shared this ‘unicorn-building GTM playbook’ with me on episode 2 of our PeerSignal Podcast.

What you'll learn in our conversation:

* How they close 7 figure deals by getting Fortune 500 executives to eat helium-filled sugar balloons.

* Why they 3.5Xd their SDR team (and enterprise sales is NOT dead).

* How and why to avoid "The PLG Trap".

* When to say no as a marketing leader.

* How to differentiate AI with real value.

* The "Bullseye" framework for account selection.

My takeaways from our talk:

1️⃣ Your brand is built on customer outcomes

Differentiation isn't about features anymore - it's about proof. "Anyone can build a demo in a couple days. Getting it into production at enterprise scale is really freaking hard." Let your customers' results speak for themselves.

2️⃣ Wining and dining still works

Wining and dining works, but you have to go all-in. Courtside seats to watch Luka return to Dallas. Private dinner at a michelin restaurant. These are the experiences that earn you enterprise relationships. "I've never seen senior executives like this in 25 years." That's what Russells CEO told him at one of the dinners, and it was the moment Russell knew it was working.

3️⃣ Follow value not hype

When deciding who to target, focus and maximize the center of your bullseye-- where you deliver the most true value for customers. This is how you deliver real business value, and earn executive credibility as a marketing leader.

4️⃣ Raving fans are your best marketers

"Our number one operating principle at Gong was to create raving fans." Russell's teams don't just deliver software - they get customers promoted because of their products. When customers become evangelists, everything gets easier.

Full Interview: https://www.peersignal.org/podcast

Would love to hear from you!What did you think of this episode? Who do you want to learn from? What else do you want us to dive deep on?Reply to this email, I read every one :)

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org

Elissa Fink is the former CMO of Tableau, where she led the company from roughly $5 million to over $1 billion in ARR. After a storied career building one of the most beloved brands in B2B software, Elissa now sits on multiple boards and advises CMOs on how to combine brand and demand into unstoppable growth. In this episode, she joins host Adam Schoenfeld to unpack lessons learned on everything from marketing’s role in the boardroom to preventing small “trash can fires” from turning into full-blown “house fires.”

What You’ll Learn

How to communicate with the board so they truly understand marketing’s impact (without bogging them down in every funnel detail)

Why brand and demand go hand-in-hand—and how every “demand touch” is also a “brand touch”

The difference between good CMOs and great CMOs (hint: it’s all about curiosity, adaptability, and team empowerment)

Actionable tips for preventing small issues from becoming big crises, including Elissa’s “trash can fires” framework

How to maintain brand authenticity at scale and avoid “best-kept secret” syndrome

Elissa’s biggest ‘How to Fail as a CMO’ pitfalls and the importance of aligning with sales for overall company success

In This Episode, We Cover

(00:00) – Intro and warm-up• Elissa and Adam settle in, adjust cameras, and talk dogs, kids, and music before kicking off

(04:02) – The official start: Brand vs. Demand• Why every demand initiative also affects your brand and how to keep messaging consistent

(07:00) – Marketing’s seat at the board table• How boards think about marketing, what they really care about, and how to show competence

(14:00) – Good vs. Great CMOs• Why a fixed playbook can fail and how curiosity unlocks better problem-solving

(20:00) – Storytelling that resonates in the boardroom• Turning data into powerful customer narratives that remind stakeholders why they invested

(28:00) – “Pipeline is permission”• Ensuring your demand efforts drive real revenue, giving you freedom to invest in brand

(34:00) – How to fail as a CMO• Elissa’s tongue-in-cheek “chapters” on what not to do—from refusing to delegate to playing politics

(39:00) – Trash can fires vs. house fires• Identifying small problems early so they don’t become organizational crises

(45:00) – Brand authenticity at scale• Examples from Apple, Snowflake, and HubSpot on consistent messaging and mission-led marketing

(53:00) – Maintaining a clear head under stress• Elissa’s personal strategies for staying grounded and action-focused when chaos hits

(58:00) – Other marketing leaders to watch• Elissa’s shoutouts to top CMOs—what makes them excel and where to learn from them

(01:03:00) – Wrap-up and final thoughts• How to get in touch with Elissa, her perspective on lifelong learning, and parting advice

Enjoy this conversation with a legendary B2B marketer who helped build an iconic brand and continues to inspire the next generation of CMOs. If you’d like to connect with Elissa Fink, find her on LinkedIn or email her directly at [email protected]. And if you have questions, comments, or want to share your own marketing stories, reach out to Adam Schoenfeld any time.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.peersignal.org