Dave Gerhardt breaks down why most B2B communities die, what it takes to build one that compounds over time, and why he refuses to invest in attribution dashboards.
47 min.
host—JORDAN CHENEVIER-TRUCHET:
Hey Dave, welcome to the show.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Hey Jordan, thanks for having me.
host—JORDAN CHENEVIER-TRUCHET:
Dave, you're Executive in Residence at Balderton, which closed $1.3 billion in new funds in 2024 — the largest combined early and growth funds ever raised for Europe. Congrats. For people who aren't familiar with the term, it usually means a senior operator embedded inside a fund, advising the portfolio. What's your version of it at Balderton?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
It asks me to make a distinction between entrepreneur in residence and executive in residence. It's a very fine distinction, lost on most people, but I'm technically an executive in residence. An entrepreneur in residence is, as you said, an entrepreneur — they're looking to get back into the game, they're watching the deal flow and going: ooh, I want to join this team. And for that reason, some people are threatened by them. Is this our new CEO that the VCs are going to inject into my company? At Balderton, we went for the executive in residence model because we didn't want that kind of fear. More importantly, we recruited people who don't want to get back into the game. We enjoy playing the game, but none of us — there are four of us — is looking for a full-time job inside a software company. Been there, done that. Our model is highly experienced people who, for whatever personal reasons, still want to be involved and share their knowledge.
host—JORDAN CHENEVIER-TRUCHET:
Just because I'm curious: how does an American end up advising a European VC?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
That is unlikely. I think I'm the only Balderton team member who works in California, or even in the US. How does that happen? I know Bernard Liautaud, the managing director, because he was a co-founder of Business Objects. I spent nine years at Business Objects, five of which in Paris — I moved there shortly after the IPO, spent five years, moved back, then four more years working out of our US headquarters in San Jose. So really two things: one, it built my network with people like Bernard. And two, let's just say it gave me special skills about what it's like to build a European software company in the United States.
host—JORDAN CHENEVIER-TRUCHET:
Let's dive into marketing. I think you've got a story to tell about Oracle, back when it was Relational Software at thirty million dollars. What did you see there that pulled you into marketing rather than product?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
This could be a long story. I was a self-taught programmer — programming on paper tape, over modems, to IBM mainframes, as a child. I paid for college by programming at Lawrence Berkeley Lab. Then I needed a job and ended up at Ingres, one of the original four relational database vendors, then known as Relational Technology. And we had this nasty competitor across the bay called Relational Software. Their product was called Oracle — if you go back far enough, the company was Relational Software and the product was Oracle. Over the next seven years at Ingres, I moved from tech support into competitive analysis into product marketing. But the more important thing was: the company was losing to Oracle, and that was very confusing to me. We were founded by four UC Berkeley professors, one of whom would win the Turing Award 40 years later. The very first CTO I ever worked with is going to be the best of my whole life, bar none. And we kept losing anyway.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
That, to me, was intriguing. I just said: whatever this sales and marketing thing is, it seems to matter a lot, and I'm going to go learn it. Because we had all the technology in the world, yet we were losing — commandingly, not just a little. I went on a sales call once where the customer said: Dave, before you begin, you should know that if you prove to us you're as good as Oracle, you lose. If you convince us you're 20% better than Oracle, you lose. And maybe, if you convince us you're 50% better than Oracle, you've got a chance. The first thing that went through my mind was: gosh, we're going to lose this deal. The second: how could I get my company into that position? Wouldn't it be nice to be the other guy in this transaction?
host—JORDAN CHENEVIER-TRUCHET:
So this is when you realized sales and marketing was everything in the company.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Yeah. A lot of founders to this day — particularly European founders — would dispute that notion. But I had imprinted on my brain, very early in my career, that best product doesn't win. Therefore there's this thing called sales and marketing, and I'm going to go learn it. For a bunch of personality reasons I'm more suited to marketing than sales, so I built my career in marketing. But that was why: because I watched Ingres lose.
host—JORDAN CHENEVIER-TRUCHET:
For people who don't know, you write a lot — you've got a blog, which you recently modernized. In one of your pieces you described the evolution of software marketing as shifting from "go get leads" to "go get customers who renew and expand". If you had to write that chapter today, what's the next "hey marketing, go get this"?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
I won't get it perfect because I'm doing it from memory. When I started, marketing departments were told: hey marketing, go get leads. You'd go to a trade show, leads were on paper, and the number of boxes was the success metric — hey, we filled two boxes of leads. Then somebody figured out that a lot of those were students, analysts, consultants. They were never going to buy anything. So it became: go get qualified leads. Then CRM came along and it was: go get opportunities. Then somebody said not all opportunities are created equal, we'd like bigger ones — so go get pipeline. Then: not all pipeline is created equal, go get weighted pipeline. Then: weighted pipeline doesn't convert, so go get pipeline from deals that will close. Then closing wasn't good enough — we care about NRR here — so go get opportunities that turn into pipeline, that we win, and that renew and expand on renewal. That's literally 30 years of my marketing career distilled into "hey marketing, go get this".
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
So what are they telling marketing to get now? A lot of this is driven by your pricing model. To the extent people are moving to outcome-based pricing, it's going to be: go get customers who drive outcomes. Customers who are successful using the product, and who use a lot of it over time.
host—JORDAN CHENEVIER-TRUCHET:
What do you think of organizations still asking marketing to go get leads?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Part of this is supremely frustrating to me, because any good marketer would know the following. It could be 1989 and I could have a box full of leads — look, you want the team fired up about getting leads, that's how you make a trade show work. You pump everybody up: go run cards, go talk to people. But then you filter them quickly and throw away the bad ones, because as a good CMO, you know the point is sales. I worry a lot of bad marketers forget the point. There's this big MQL backlash now — "the MQL era is dead". Well, MQLs were the only thing you ever wanted if you were a bad marketer. A good marketer knows you want MQLs that turn into deals. A lot of the rhetoric around marketing — the MQL era is dead, performance marketing is dead, it needs to be all brand — is founded on these miscomprehensions. If you always understood that the point of marketing is to make sales easier, you wouldn't get this wrong. So if it's 7:55am and the booth opens at eight: yes, go get leads. But that was never the raison d'être of marketing.
host—JORDAN CHENEVIER-TRUCHET:
Going back to outcome-based pricing — I see two types of companies now. It works really well if you help a company produce a lot: that's what we see with the LLMs, where the outcome is the tokens you burn. On the other side, you've got revenue or results as the outcome, and as a vendor you take a lot of risk attaching your pricing to that. I feel a lot of companies will choose production over revenue as their outcome. What kind of risk are they taking?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
I love analogies, so here's mine for outcome-based pricing. Say we run a dating site. What's an outcome? Is it a first meeting? A date? A relationship? An engagement? A marriage? A marriage that lasts ten years? Back to "hey marketing" — marriage is not good enough. It's easy to get simplistic about outcomes; even in that simple example, what is the outcome anyway? And by the way, if I know the conversion rates, I can build you a pricing model that's mathematically equivalent at every level. You want to buy dates, they cost this much; you want to buy engagements, they cost a lot more. If I know the funnel, I can price it to be mathematically equivalent on average — it's not hard. So one question is what the customer wants to buy. Most people are optimistic, so they'll want to buy dates, because they're cheaper and they overestimate their conversion ratio. There's a lot of psychology in the pricing.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Then: some companies are not blessed. Twilio — you send an SMS message. Is that consumption or is that an outcome? Twilio can't guarantee the outcome. If the SMS is a marketing promotion, they're not in the business of getting paid on whether that promotion works. I call these intermediate outcomes. If you're Twilio, it's probably an outcome — we sent the message, we did our job. If you're the marketing software built on top of Twilio, it's not an outcome, it's an enabler. So: one, outcomes are elusive. Two, not everybody has them to price. The best thing in the world is selling resolved cases — that's why everyone uses support as the example for outcome-based pricing. You can do it with a chatbot, and there's an equivalent human cost. SDRs converting MQLs to opportunities: same thing. Those are great use cases because it really is a business outcome, and I know exactly what it would have cost with a human. Not everybody is in that situation — that's why Salesforce created the agentic work unit. Everyone's struggling to find something above tokens, which is really a language-processing metric. But it can't all be closed deals either: if you're writing bad marketing content and I send your message, it's not my fault if it doesn't close. So they're trying to create these intermediate layers.
host—JORDAN CHENEVIER-TRUCHET:
You mentioned that marketing has to make sales easier, and I know a lot of CMOs who don't really think that way. It's a principle you picked up at Ingres. In 2026, what makes the job of sales easier? More data? More content? More AI-generated pipeline?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
First, the basics of the principle. I was in a meeting decades ago as a product marketing manager. We'd brought in a new VP from Oracle — Chris Greendale, charismatic guy. He stood up and just said: why do we exist? We exist to make sales easier. Literally, as soon as I heard it, I thought: I like this guy, and I like this mantra. In consumer products marketing, the PMMs are the brand managers and they're the bosses — sales are soldiers they deploy. And a lot of tech marketers deep down wish for that power. So there's this tension: is sales the customer, or is sales our pawns on the chessboard? In an enterprise software company — given how much money salespeople make, how much the department costs, how much power they have — it's a really bad idea to treat them as pawns. You will not last. Go sell yogurt or candy bars if you want sales to be your pawns.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
A couple of years later, I worked at a company where the head of sales came in one day with t-shirts that said: code, sell, or get out of the way. I thought it was fantastic. Two people make money for this company — the people who write the product and the people who sell it — and everybody else is help. Even the CEO is help in that definition, unless they're on a sales call. I later wrote a post called Enterprise Software as a Two-Engine Plane: two engines of flight, code-writing developers and quota-carrying salespeople. That's always been my philosophy. And the first thing about it is that it's egoless: yeah, we're help, and we're proud of it. We're here to help you — which means we need to ask if we're helping, and measure if we're helping. There's a psychological part some people still resist, because they're too proud to admit they're help. If the company had only three people, there'd be a CEO, one developer and one salesperson. Zero marketers. And by the way, that mantra — from the second I heard it — took me from PMM to CMO of a billion-dollar company. It works. I'm a big testimonial for it.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Now, how do we make sales easier today? Take a funnel view. You can put more in at the top of the funnel, with higher quality — and the CFO will like you if you do it with higher efficiency. Most marketers are very focused on top of funnel, arguably too much. I'd even say they're one level down: focused on what marketing circles call demand capture. You didn't actually generate the demand — you found a guy who was out shopping. That's very important, that's what builds pipeline. But demand generation matters on top of that. You may know Alice de Courcy from Cognism — she did a ton of really good content on demand gen versus demand capture. Everything you want to know about that, go ask Alice. But being a product marketer by background: there's a lot of value you can add lower in the funnel. Better messaging, better competitive messaging, better tactics. If we know the competitor goes to end users with a demo to show ease of use, we counter by going to IT with a security message. That's not a product message, that's a sales play — but marketing can help with that, working closely with enablement. So I'm a full-funnel marketer: if it's anywhere in the funnel, we can help.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
I viewed myself as a doctor: tell me your problem, I've got this medical bag full of medicines, and let me make the diagnosis. Because salespeople aren't great at diagnosis. Eight out of ten salespeople will tell you the marketing problem is "nobody's heard of us". If I could just get more at-bats, I'd get more runs. That's always true — but is it the most efficient way to get more runs? Maybe we need to increase your on-base percentage instead. There are a lot of other levers. Sometimes I call it tough love, sometimes the doctor-patient relationship: I'm here to help you, but I am a professional, I've studied this for 30 years. So how about you don't tell me the answer — you tell me your symptoms, and I'll tell you your disease.
host—JORDAN CHENEVIER-TRUCHET:
It's interesting that you mention ego. I run a service company, and I see a lot of agency owners who dream of having a SaaS business because it looks sexier — they don't like being at the service of others. I find it pretty noble. Saying marketing has to make the life of sales easier doesn't make it a bad job. It's actually great.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Totally — if you embrace it. Some people don't. It came very naturally to me, but I've met people who think sales are the pawns. In consumer they are the pawns — I have friends in CPG marketing, I understand where it comes from. If you went to a CPG-oriented business school, you got shaped with the wrong notion of what sales is for enterprise software. But there's nothing better than being help. When you embrace it, you do better at it. How can I help? And then: wait a minute, I'm also a professional. So let's hear your challenges — and I'll apply 20 years of experience to answering that.
host—JORDAN CHENEVIER-TRUCHET:
You wrote that in 2025 most of the VC capital went to AI-native companies, and that traditional SaaS risks becoming zombies. For a CMO working in a traditional SaaS, that sounds risky. What does he or she do in the next few months?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Let me explain the point of that post. Back in the old days, you could bluff your future story. If somebody said "you're an on-premises vendor", you could say "but we're building a cloud offering" — and that was good enough. You could show up as a regular on-premises vendor, sell a cloud story, and raise money. People were a lot more patient then. The main point of the post is: that doesn't work anymore. "We're a traditional SaaS vendor but we've got a great AI story under construction" — doesn't work. If you want to position a great AI story, you need a great AI product and a great AI growth rate to go with it. And if you don't, then you should be profitable — a good financial investment. The zombie is the company in the middle: $20 million, growing 13%, break-even. Nothing exciting as a financial investment, an AI story but no AI product — so the story value gets discounted to zero. Without this framing, you could end up there thinking "we got away with it last time, we can sell the story". The answer is no. There's no middle ground anymore. If you're the CMO, all you can do is talk to the CEO: hey, what are we doing? Either we push profitability, or we do something to get an AI product — acquire something, do a tuck-in. But we can't kid ourselves that a deck about an AI product coming in two years is going to impress anybody.
host—JORDAN CHENEVIER-TRUCHET:
Maybe a tricky question. I feel it's really hard right now to tell the difference between a true AI-native product and a wrapper. A lot of companies invest in AI internally or in their product and feel they're AI-native. What's your true definition?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
A couple of things on what I see out there. The most frustrating place is the people who were into AI about five years ago — call them AI 1.0. They actually had a native AI story — it was just native AI machine learning. The wrong native AI. Those people I feel for; they're deeply confused: "but we are native AI, we got our master's degrees in AI and founded the company". That's the hardest case. Next to it, the traditional SaaS company: just having a copilot or a little bot on the side is not going to be enough. Orchestration might be — it doesn't have to be a thick orchestration layer, as long as it has domain knowledge in it. I believe small SaaS companies do well by knowing a problem space really well. I don't care how thick the technology is. I care how easily someone else could build it — particularly if they don't know the space as well as we do. That's where competitive advantage comes from: we know everything about dentists, we built a relatively thin AI orchestration layer, but it does everything a dentist wants.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
And this is why I want the growth rate — I'm not fundamentally a technologist anymore. I can get into a long theoretical discussion about whether something is AI-native, whether it's thick or thin, what the moat is. But the first test is: is it selling like hotcakes? If it's not selling like hotcakes, I don't care. That's why I say you need a native AI product and a native AI growth rate — and I'm much more flexible on the definition of the product than on the growth rate. Otherwise you're bolting some AI onto the side of an existing offering. That's not bad — it'll probably help you sell your existing offering to existing customers — but you haven't changed anything about the company. If you're trying to say "we've done an AI pivot", I need to see more. And the proof isn't found in the slides. It's found in the growth rate. We could do it with slides before; it doesn't work anymore. People go: great slides, what's the growth rate? Thirty percent? You're not going to be able to raise money.
host—JORDAN CHENEVIER-TRUCHET:
Let's talk about trust. Every year you write predictions, and in your latest ones you said: only trust will get emails opened, podcasts listened to, reviews believed. At the same time we've got AI content everywhere — fake reviews and everything. If trust is the last marketing moat, how do you actually build it?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
It's a tricky question. I'm somewhat contrarian in general, and I watch the world generating AI slop left and right. There was this era of gated content — I never liked it. My blog has always been ungated, and even with companies I worked with, I was always asking: do we really have to gate this? The better a piece of content is, the more I want it out — I want people to hear our point of view. I would never gate a white paper with our industry point of view. I might gate a benchmark study with numbers people want. Marketing was gate-slash-MQL oriented for so many years — the gate is what captures the MQL — and that's what people mean by "we had it all wrong with MQLs". You didn't have to get it wrong. Just ask intelligently: what's more important here, getting the word out or getting the MQL? If it's a tactical piece and I need MQLs — boom, gate it. But if it's our worldview and why you should move to our kind of architecture, that should never be gated.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Against that backdrop, you now have the ability to generate a hundred times more content — a hundred times more MQLs! But people don't have a hundred times more room in their brains. And people are very good at detecting AI slop. My primary slop detector is when my brain stops while I'm reading something. What just happened? Why did I fall asleep in the middle of this piece? Then I look at it and see the em-dash, the "it's not this, it's that", all the telltales of AI writing. I've always believed a couple of first principles. One: people are smart, and we should respect that. Two: interested buyers will read long content. This goes all the way back to David Ogilvy — long copy sells. Don't only produce morsels of content because "people don't have time anymore". People have time. If they're betting their job on buying a financial planning system, trust me, they have time. How long is the average episode of Acquired — four hours? People have time, when you've got good content on something they care about. I've always preferred those first principles to "make your blog post 217 words and include these keywords". That stuff doesn't work. AI just put an amplifier on all of this: it's easier than ever to generate ten times more slop. I think it's an opportunity to not be in the slop. Or at least to keep a special reserve — the founder's reserve, the wine cellar: this is the good stuff, ungated, with our real principles. Maybe you do syndicate crap everywhere just to get the leads — I'm a pragmatist, maybe you have to. But somehow you indicate: this is our primary resource library.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
And it means don't make empty marketing claims. How do you lose trust? The expression is: trust is gained in drops and lost in buckets. You gain it very slowly by always being credible, never exaggerating your claims, putting a hard filter on what you produce: does this read like marketing jargon junk, or like something an intelligent person would say? In every little thing you do, you keep the trust level high and you resist the seduction. Because it's lost in buckets — you screw up once and you can lose a year of work. I don't have a simple solution, but: run high-trust communications, and you'll get rewarded over time. Your competitors are going to slop people to death, people will stop opening their emails — and people can tell quality content.
host—JORDAN CHENEVIER-TRUCHET:
You also said PR is the new SEO. Is that the continuation of this thought?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
That one was more tactical than intended — these are annual predictions, and I think that one lasted about a year. I've always considered SEO trench warfare: it changes every day, you gain a yard, you lose a yard. And AEO is the same. At the time I wrote it, one of the best ways to get good AEO was to be featured in a Wall Street Journal article, a Forbes article, Fortune, the Financial Times. Authoritative big press was one of the best things you could do for AEO. And I just thought it was hilarious — we've gone full circle. For a decade we killed PR, didn't care about PR, and all of a sudden PR is one of the most effective ways to get good AEO. I found it ironic and funny. Now I think that's passed a little. For a while it was Reddit — you had to have your Reddit content. Fact-structured content is important. And I think YouTube is now super important — they're changing their algorithms. So not a multi-year prediction, but hopefully correct for the year I made it.
host—JORDAN CHENEVIER-TRUCHET:
One thing that's hard for most CMOs: PR is this black box with murky ROI. How do you manage it?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
There's definitely bias in anyone's writing — I think companies underinvest in PR. So not only did I enjoy the irony, it was another angle to say: you should invest in PR. I know two-hundred-million-dollar companies that don't have a PR firm on retainer or a PR person. If you're ten or twenty million, okay. But if you're one hundred, two hundred, five hundred million — I don't know how you don't have a PR team. You have to be careful how you aim it, and PR has changed a lot, but I've always been a huge believer, because it's earned media. It's kind of free: if you're clever and know how to work the system, you can get a lot of awareness and impressions at relatively low cost. It's also good for relationships. The vast majority of market-leading companies are good at PR — it's part of what makes them. You can argue Andreessen Horowitz made themselves with PR: they hired the woman from OutCast to run communications when they were relatively new. What's the cart and what's the horse at Andreessen — the investments or the PR? I think the PR did an enormous job for them. But you're right: it's expensive, it's a black box, you can waste a lot of money. So do it with a contractor, part-time. When your story is good and topical, you can execute — and you're not carrying a fifteen-thousand-dollar-a-month retainer when it's not. There are very experienced PR pros who've retired and still want to work. There's a way to have PR without saying no to PR.
host—JORDAN CHENEVIER-TRUCHET:
There's also the attribution topic — PR is really hard to measure. On this you said: metrics reflect strategy, they don't drive it. I find this claim really interesting, because most boards ask their CMOs to be metrics-driven. How do you manage that tension?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
If I'm anything, I'm a strategy-first business person. Strategy is a big fancy word, but the best definition I've heard comes from the preface of Rumelt's book, where a professor who's been attending his class says: "it just seems like we spend a lot of time here trying to figure out what's going on." Yes — that's strategy. If you can figure out what's going on, you can know what to do about it. The knowing-what-to-do part is actually not that difficult; the figuring-out-what's-going-on part is exceptionally hard. So we figure out what's going on, build a plan for executing within that, and use metrics to measure progress on the plan.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
To take it back to marketing: we've been through an era very focused on performance marketing, so all the performance marketing metrics are in vogue. If you believe, as I do, that the pendulum is now swinging back towards brand — more and more marketers are saying performance channels are saturated. Google has optimized paid advertising, from their perspective, to the point where it's barely cost-effective for me. Which in some sense is their job: that's the equilibrium they want. The strategic view says: these channels are saturated, we allocate less money to them, more higher in the funnel, more to demand generation than demand capture. And therefore we can't run on the same metrics. The new metric might be market research on awareness, positive opinion, consideration — as opposed to just counting MQLs and opportunities. Marketing is always a triangulation problem; you should look at all of it. But you don't start with "I've got a compass that measures direction" when what we care about is altitude. Wrong tool. Figure out what you want, then find the device that measures it.
host—JORDAN CHENEVIER-TRUCHET:
It's funny — I asked about metrics and you said you're more into strategy. But everything you write is really scientific and mathematical. There are a lot of numbers and calculations.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Really good observation. It's also true of execution. People say: Dave, you call yourself a strategist, but you're an execution fanatic and a metrics fanatic — help me reconcile this. The answer is pretty simple. Execution first: if we execute badly and something fails, I learn nothing. I don't know if it was a good idea or not. I always say: you're spitting in my petri dish. Bad execution ruins the experiment. I'm trying to figure out if we can sell this thing to mid-sized insurance companies, I've got three sales reps trying it for six to twelve months — and if you hire three clowns who don't show up to meetings and we don't sell anything, I learned nothing. You let your bad execution blow up my experiment, and now I've truly wasted a few million dollars. Whereas if we hired three aces, they did their best, and it didn't work: okay, we can safely exclude mid-market insurance from our target markets. I feel the same way about metrics: they let me measure progress in the experiment. They're my way of knowing, objectively, whether something's working. And a lot of my favorite measurements are actually strategic — market research: have people heard of us? What do they think about us? Why aren't they buying us?
host—JORDAN CHENEVIER-TRUCHET:
You wrote about the three ways to get fired as a CEO. I wrote them down:
host—JORDAN CHENEVIER-TRUCHET:
What's the equivalent for CMOs?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
We were talking about this earlier — I think we came up with a good list. One: "I don't want to be accountable for a pipeline target." Great way to get fired. Two: "I don't want to do attribution, because it's too hard and it doesn't really work." That one's more subtle, because attribution is imperfect. But as I always say: until the CEO, the CFO and the board stop asking, you need to keep answering. If you know a better way to answer, please tell me what it is. I'll be the first to concede that attribution is imperfect — but absolutely necessary. You need a kind of schizo view on it. The business will not stop asking, and it's not good enough to say "it's really hard to measure". Some CMOs try — it's a good way to get fired. It's a weird learning cycle: when you know a little about attribution, you're super jacked because you think it works. Then you learn more, discover all the limitations, and go super negative. Then you need to come back up: people need it anyway, I need to provide it anyway, and my job is to limit the misinterpretation of attribution data when I present it. That's the actual challenge of the CMO. And third: "there's nothing I can do about win rate." A lot of marketers are too top-of-funnel oriented. If we're only winning 5 or 10% of our stage-two opportunities, that's not good enough. I'm Doctor Marketing, I'm here with my bag — let's look at what's going wrong and see if we can get that win rate up.
host—JORDAN CHENEVIER-TRUCHET:
What's interesting is that we can sum them up as: they don't take accountability, or they don't realize the impact they can have on sales.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
True — refusal to take accountability covers the first two. And on win rate, I overstated it: it's both a marketing and a sales problem. If we can help, it's part of our problem.
host—JORDAN CHENEVIER-TRUCHET:
You've written about the decomposition of marketing into distinct pillars: PMM joining product, demand gen joining sales, brand joining the CEO. What's your view of the marketing department in 2030? Because if we go this way, there is no marketing department.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Just to be clear: I wasn't recommending this as the ideal marketing structure. I was saying — and this is true — I'm seeing it more. Literally, I had one CEO say to me: Dave, I've had four CMOs in five years. I can't do it again. Don't make me touch the hot stove again. I don't want to hire a fifth CMO. That's the only case where I've actually recommended it. But I've seen it happen a lot. You put product marketing under product — that works when you have a marketing-y product head. We did it at Salesforce: all the product GMs, and I was one of them, were pretty marketing-oriented people. It creates a problem: if you have multiple products under four different GMs, who tells the whole story? That creates a need for what I call product-line marketing in the central org. You can put demand gen under sales — I don't love it, because most salespeople aren't that interested in it, but you can do it.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
My test for when it works: if the CRO says "Dave, I want to be president and then CEO one day. I want to learn marketing, and integrate it better into my org" — I love it. That's a good reason. If it's just self-preservation — "those guys can't generate enough pipeline for me, and my health was at risk, so I'm going to own it" — I don't like it. We can find a CMO who will care about you. If the problem was a CMO who didn't care about demand gen, fix it by replacing the CMO, not by moving demand gen under the CRO. And brand and comms typically end up under the CEO. In those orgs you have no CMO — or you call the brand-and-comms head "CMO", the hollowed-out CMO job, which is not uncommon. Look, I don't recommend this except in "I can't do it again" situations. But I'm seeing it happen more and more, and I understand why: CEOs are frustrated they can't find the all-sport-athlete CMO. They can't find it, so they fail, and they decompose the role. I hope the pendulum comes back on this one — I believe in CMOs. But right now, this is what's happening in the industry.
host—JORDAN CHENEVIER-TRUCHET:
Let's take a step back. You've worked both sides of the Atlantic. What's the most misunderstood difference a European founder has about the US market?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
I'll give you two. One: the commitment required, in time, money and effort. They underestimate how big a deal it is — including Business Objects, where I did it firsthand. Two: the importance of marketing, image, brand. If I have to grossly stereotype product-oriented European founders: they have yet to learn the lesson I learned at Ingres — best product doesn't win. They're smart enough now not to say it. Ask them "do you think the best product wins?" and they'll say no, other things matter. But deep down, I think they still believe it. Deep down, American CEOs understand that marketing and sales have a huge impact on the outcome. European founders might even be in a more dangerous middle ground: they accept it verbally, or pretend to understand it, but they don't. They still think that if we show up with a good product and show it to people, we'll win. That's simply not true — I don't think it's true in Europe for that matter, and it's definitely not true in the US.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
And I have to mention one more, because it comes up so much: the value of their references. Unless you're a vertical player whose European customers are known worldwide in the industry — if you're a horizontal player and you show up saying "we've got great references: Bouygues, Carrefour, ASML, Reed Elsevier" — not only have most Americans not heard of these companies, they can't pronounce them. These references are just not useful. And that's really painful for the founders, because they built these amazing accounts into big successes, and outside their vertical they're worth nothing. So try to get global brands on your European customer base, or accept that you're starting from scratch in the US. Schneider Electric is not a reference that's going to carry you real far over there.
host—JORDAN CHENEVIER-TRUCHET:
Say I'm a European scale-up founder and I want to go to the US. Where do I start? I understand I need my main use case in the US — go shake hands, get my first customer, make it a really good use case, then take it to other companies in the same industry. Correct?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Yeah — that's Geoffrey Moore 101, the bowling alley strategy. Find a use case, find an industry, and go press the flesh. But let me give you an alternative tactical view: where do you start? New York. For eight out of ten European startups, New York is the answer.
host—JORDAN CHENEVIER-TRUCHET:
Why? Especially in tech, I'd think San Francisco.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
What's the New York advantage over San Francisco? Closer flights, less time difference, the most culturally compatible city. San Francisco is pretty culturally compatible too. But you want to save money and open in Atlanta or North Carolina or the Midwest? I just think it's harder for European founders and their partners to be happy living in Atlanta compared to New York. And those things matter, because if we're going to relocate a founder — which I also recommend — they have to stay. They can't leave after six months because their partner says "I've got to get out of here". New York is a good location, you can find talent, and there are multiple industries all around: pharma in New Jersey, insurance in Connecticut, finance in New York. Great flights across the US. It's just a really good hub. At Business Objects I flew Paris–San Francisco almost once a month for nine years, and I can tell you: it's tiring, and the time difference is bad. Now, if I'm a hot AI company, I may have to do San Francisco — that's the only exception. The AI scene is happening there, so if you're related to foundation models or core AI technology, that trumps New York. But for a typical company: open a New York office, and move a co-founder there.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
And then I've got to talk to you about how to read US resumes. Probably the single funniest thing a European founder ever said to me — he was looking at a pile of American resumes — was: "these people are gods." I said: no, that's just a schleppy sales rep from New Jersey. You think they're gods because you don't know how to read American resumes. American resumes are embellished. Europeans understate their accomplishments; Americans overstate them. So you look at an American resume with a European eye and think: these people are gods. No, they're not — and we need to teach you how to interview them. Behavioral interviewing is hugely important here, because it forces people to tell stories about actual things, and it cuts through the embellishment. If you ever wondered why behavioral interviewing is so popular in the US: that's why. US resumes are super inflated, and this is the antidote.
host—JORDAN CHENEVIER-TRUCHET:
It's funny you say this — all the French founders I know who went to the US to hire salespeople told me exactly this. A hundred percent of the time.
host—JORDAN CHENEVIER-TRUCHET:
One last question. What's the one thing you look for in deciding to work with a founder — or giving a positive rating in a diligence process?
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
That one's tricky. My first rule of founders: all founders are crazy. They have to be, definitionally. They're quitting a perfectly reasonable job to start a company that's a one-in-a-hundred or one-in-a-thousand shot. Sometimes VCs wish for sane founders — that's just not going to happen, they don't make them that way. So you need to pick what kind of crazy you want. They come in different flavors of crazy, and I like some flavors better than others. That's the first principle — not a qualifying criterion, an ambient criterion. If I had to pick one thing I like: curiosity. I'm a huge believer that curiosity is the number one thing in sales. And to the extent founders need to sell, curiosity is just so powerful. You want to learn about what you don't know — that makes you a better founder, because you're always learning, you're not pretending to anybody that you know everything. "Hey, I'm a product guy, I built this thing. I know a ton about the product, a little about the space. I'm curious — how would you use it?" Almost every single important question in a sales cycle, you can get to just by saying "I'm curious": why do you want to buy this? Why did you call us? Why would you ever buy from a little French startup? Have you ever bought one of these before? Has anything changed? It also applies to becoming a better CEO — going to your investors and mentors: I'm curious, how have other CEOs handled this situation? And being curious with customers about their problems: why is this a problem? How have you tried to solve it before? When you're done solving it, what's the next thing you do? That general curiosity helps you find where you fit in the value chain, and it helps you find adjacent expansion opportunities. So if there's one thing: always be curious. What don't I like? Defensive founders. Proud founders — people too proud to admit they don't know what they don't know. They're going to be too proud in sales calls too, they won't find out, and they're going to lose. So curiosity is the thing.
host—JORDAN CHENEVIER-TRUCHET:
Thank you very much, Dave, it was great. For people who want to know more about what you're doing or contact you, we send them to your blog and your LinkedIn.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Yeah — kellblog.com, my LinkedIn at /kelloggdave, or my Balderton email if you want to reach me: dkellogg@balderton.com.
host—JORDAN CHENEVIER-TRUCHET:
We'll put all the links and contacts in the description of the episode. Thank you again, Dave. See you next time.
guest—DAVE KELLOGG—Executive in Residence @ Balderton Capital:
Thanks, Jordan. Thanks for having me.
host—JORDAN CHENEVIER-TRUCHET:
Hey everyone, and welcome to the show.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Thanks for having me.
host—JORDAN CHENEVIER-TRUCHET:
Bruno, you've been at Clay about two and a half years now. Since you arrived, everybody I speak to in B2B and every company I work with has heard about Clay — they want to work with Clay, they're Clay users. You've managed to be everywhere and make sure people talk about you. You've got this content playbook: founders speaking online, the team, creators, agencies. How do you manage the whole thing?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
There are two sides of this. One is the content that people in our community create — or people in general who aren't even associated with Clay. The other is the content that we create ourselves.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Let me start with the community side, because that's the one people have the most questions about: how are we getting all these people to talk about Clay? The first element is that Clay is a very flexible and powerful product. When you look at the market for sales automation and data enrichment in B2B before 2023, most products were inflexible, with a sales-led motion. Clay came in self-serve, very flexible and horizontal. So people could actually build on top of it. The product unlocked a lot of creativity — people could create go-to-market workflows they could never build before.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
That's the foundational layer. As people build these things, a portion of them are service providers — they have freelance businesses, agencies, or they're individual contributors who want career progression. Clay enabled them to showcase to the market that they were very innovative. I saw a similar pattern before Clay, during my five years at Webflow, and on design and developer tools too.
host—JORDAN CHENEVIER-TRUCHET:
Notion is a good example of that.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Notion, Airtable early days, Webflow, Framer, Figma. The flexibility lets people showcase. The tricky part as a marketer is: how do you have any control? The way we found is by creating programs in the community that incentivize people in a soft way. And I say soft because — this was a learning — most of these people don't want “post this and I'll give you X.” What they want is brand association with us.
host—JORDAN CHENEVIER-TRUCHET:
So not basic sponsoring.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Right. Clay was innovative in the market and people wanted to be associated with that. So the question became: can we build programs that give this brand association, which then increases the output of content they create? We built the Experts program — now the Solutions Partner program — the Creators program for people getting started, and a lot of educational programs. The education piece is the core. They learn Clay, understand the value, get invested in the brand, create content, and distribute it on a channel.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Then there's the content we create — our executives, our employees. What we noticed early is that AI is unlocking content creation like never before. Everyone can create content today. The downside is no one is authentic. So people, more than ever, want to hear from people, and they want content that's clearly not AI.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Every company can do what we did. Clay has two sides of the business: self-serve and sales-led. Self-serve has a lot of startup founders, agency owners, and first marketers at a startup. Sales-led typically has rev ops and marketing ops as the end user, and CROs and CMOs as the final decision-makers. So we selected specific individuals in our company that match those profiles, and put real resources behind them to create content on LinkedIn relevant to that audience.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
For the ops persona, we have Everett, our head of go-to-market engineering. For the founder persona, Varun. For the marketing persona, me. For the CRO persona, Karan, who's our CFO and CRO-ish. And for SDRs, our head of SDR. We pair actual writers with these people, meeting weekly — “here's an experience I had, here's what I want to write about” — and they go back and forth and post.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
The main thing is that everything funnels into LinkedIn, because we keep seeing it's the channel where buyers spend time — we hear it constantly in how customers find us. That's why people have the impression: holy shit, I'm seeing Clay and everyone's talking about them.
host—JORDAN CHENEVIER-TRUCHET:
I had a conversation with your team, and Nancy told me you don't want to be opinionated as a product. That's interesting — Figma and Notion have to be unopinionated to offer flexibility. But when you do GTM for a team, you kind of know the playbooks. Still, you decided not to be opinionated. How do you play with that in marketing? People expect you to be opinionated because you do GTM.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Having a horizontal, flexible product is the difficult part from a marketing perspective. The difficulty is positioning: the product is so flexible that people build insane use cases. Some use Clay as the backend of tools they generate. Some use it for outbound, some for inbound. So how do you position it? That's the challenge — and also the exciting part, because Clay can serve specific problem areas really well. We can verticalize it to different industries. If you're targeting a dentist office, you can get data points you'd never get otherwise, because of the flexibility.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
We're not opinionated on how you build, and I think that's where a lot of GTM tools failed. The ones that took off — like Salesforce — are flexible. Every business is different. The data point you need to identify your ICP with 100% confidence is often very specific, and you need a flexible product to find it. Most other go-to-market products were built around one playbook that worked for one type of company — usually tied to a channel.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
But there's always a lifecycle to a tactic. It starts effective, then everyone adopts it, and we destroy the effectiveness of that channel. So you need a tool that lets you keep pushing the boundaries. I bought this, it worked for a while, now it doesn't — what else can I do? The best companies at go-to-market are the ones pushing and trying new things as frequently as possible.
host—JORDAN CHENEVIER-TRUCHET:
When you say companies built around one use case that then disappeared, it makes me think of the whole growth-hacking wave. Ten years ago on LinkedIn you'd take your cookie, drop it into a tool to scrape people. All those companies died, because now it's so easy.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
That was a huge thing when I joined Clay at the end of 2023. A lot of people were associating us with those tools — “is this even legal? It's hacky.” A big focus for us was elevating the product to show: we're not in that group, we're a legit product that legit companies use. We pushed the brand to stay a little weird, but less hacky — this is an actual product and tool.
host—JORDAN CHENEVIER-TRUCHET:
And there was always that techie, geeky vibe. With Clay everything feels smooth — you don't need to be a cybersecurity expert to use it.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Exactly. With that old wave it was always “oh my god, can you actually do this?” — and six months later it all got shut down.
host—JORDAN CHENEVIER-TRUCHET:
A few months ago Varun, your CEO, posted about why the company took so long to get to $1M ARR and then went explosive. I commented that at some point you really nailed your positioning. For a few years I was like, what's the point of this product? Then everything clicked.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
For those who don't know, Clay has been around since 2017. It took about nine years to get to $1M ARR — and then from two years ago, $1M to $100M. When we announced $100M ARR, I called it a nine-year overnight success. Everyone says “we're the fastest growing.” Sure, we're fast in the last two years. But there's a backstory of seven years where we were almost dying.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Clay was this super flexible product — a spreadsheet that built websites, no-code. But we didn't have focus; we were spreading ourselves too thin. Early 2022, when Varun came in, he understood we should focus on the go-to-market use case. A lot of people were already using Clay for data enrichment and go-to-market workflows. In 2023 we focused there, and I joined later that year to scale it. Lack of focus is the death of a lot of early-stage startups. You have to focus on a core use case.
host—JORDAN CHENEVIER-TRUCHET:
When growth hacking was a thing, there was the growth hacker. Now with Clay there's the GTM engineer. You literally helped invent a job title. Tell me the story.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
The rules are evolving fast with AI and tools like Clay. Before this wave, you had a growth or performance marketer who owned specific channels — Google Ads, SEO, CRO, lifecycle. And you had ops people who controlled the data pipelines and the CRM. What we saw early, at companies like Ramp and Rippling, is that the best people doing interesting go-to-market work were a mix of both. They were closer to ops than to a typical channel marketer — more technical, understood APIs, webhooks, all the complexity of sending data from one place to another and launching programmatic motions.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
So there was a skill gap to fill to operate at high pace. Every company defined it differently, but they all had this person. We called it the GTM engineer: the person who builds systems and automation that generate revenue — top of funnel, conversion, or expansion. Then we started creating content: here's what we're seeing. The interesting part is you need bottoms-up adoption. You tell the market what you're seeing, then watch: are people calling themselves this? Do they resonate with it? If they do, it's real. If they don't, it's just a marketing campaign. People resonated, called themselves this, companies realized there was a gap, and they opened roles.
host—JORDAN CHENEVIER-TRUCHET:
Tough question: for some people the GTM engineering role was built and marketed because it fits perfectly with your product. For some companies it's not obvious the role is needed. How do you defend against that?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Some companies call it growth engineering, some call it business systems. You can call it whatever you want — we call it GTM engineering because it's closest to the problem these people solve. I hear “isn't that just rev ops, or what growth marketing should have been?” Sure, maybe it should. But is it being done? If not, you need someone to do this work.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
I don't think it's one or the other. GTM engineering often sits under ops, but there's still a lot of scope maintaining systems, keeping data clean, keeping the stack running. You also need someone thinking about systems that generate revenue and enabling the team to build them. The problem statement has to be there: you have to build systems that integrate all your channels to generate revenue — especially as top-of-funnel channels become more automated and you need fluency connecting them.
host—JORDAN CHENEVIER-TRUCHET:
I think marketing a job title is a good thing. A lot of people call themselves a CMO because they want to be the top marketing person, but they don't really know what a CMO does. You can call it growth marketing, rev ops, or GTM engineering — but are we talking about the same thing? If you market a job description, will you attract the right people? Organizing around one job title helps everyone agree on the same tasks and objectives.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
100%. If you call it the wrong way, you might not attract the right person.
host—JORDAN CHENEVIER-TRUCHET:
For my own company right now, we're recruiting. We know the role — some call it head of growth, some head of marketing. So we use the same job description with different job titles, because the people we want to attract describe themselves differently.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Smart. That's cool.
host—JORDAN CHENEVIER-TRUCHET:
You identify creators, agencies, and you push internally for people to post. But do you push different narratives, double-check what gets posted? What control do you have over what people post about Clay?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Internally, we have someone who oversees executive content — we just hired for it. Mapping people to a specific persona gives them guardrails and direction; that's basically the only direction we give, plus it needs to be something genuinely interesting that adds value. For the external community, we don't really control it. We share our positioning — here's how we think about things — but it's weird for me to tell people what to post. It's their personality, their channel. Burn that bridge and it's over.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Some people position Clay a little off, and I'm okay with that, as long as we have people talking about us positively. Here's the key thing: you can have the right channel and people talking about you, but those two alone aren't enough. You need high frequency. If it all happens in one week at the start of the year, three months later everyone forgot about you. So you need people talking about you all the time. It's our job to give top-down direction as much as possible, but you can't fully control it — you keep the momentum going.
host—JORDAN CHENEVIER-TRUCHET:
And how do you measure this?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
We measure top of funnel through what we call qualified engagements on LinkedIn. A post has to mention Clay. Then we look at the volume of likes and engagement on those posts. We have a named-account list of who we want to go after, and we cross-reference it with the people engaging — are we attracting high-quality people? Early on we measured by raw social engagement, and some posts got tons of engagement from weird bots. That was the wrong thing to do.
host—JORDAN CHENEVIER-TRUCHET:
It's clickbait, and the engagement is bad.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
It shifted us to invest more in executive content that fits the personas, because that attracts really high-quality people. That's how we measure the top of funnel.
host—JORDAN CHENEVIER-TRUCHET:
In your Understory interview, you said importing Webflow's complex growth processes to Clay too early was a mistake — early stage needs brute-force execution over analytical sophistication. But a lot of listeners are CMOs and heads of marketing past early stage. What's the actual breakpoint?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
At Webflow I led the growth team owning self-serve acquisition — a big self-serve business. I had bi-weekly sprint planning with engineering and data science, weekly metrics reviews with leadership, a whole prioritization motion. Looking back, it made us a little stiff. When I joined Clay, I knew the playbook, so I set those things up. But the speed was so different, and Clay was 18 people — my team at Webflow was 18. Things moved so fast, at a different scale, that everything behaved differently. So I realized this doesn't work here. What mattered was shipping things — create the programs, build the motion — and then we can measure.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
For context, Clay is now around 400 people, with a marketing team of about 30. We're later stage, so we do look at the numbers — weekly metrics, a monthly retro with founders on the operating cadence. But my obsession with the marketing team is: how do we not lose speed as we grow? It's easy as you scale to become obsessed with attribution, locked into a motion where you have a meeting to present, then a meeting to prep the meeting, spending all your time pulling data.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Do you have conviction on the channels and bets you're making to solve a specific problem? We have four bets for the next six months: grow the product-led motion, grow the fast-growing sales-led motion, verticalize Clay into new industries, and international expansion. Those are the problems to solve. Marketing-wise, do you have bets you're convinced will help solve each one?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
For international expansion into Europe, we don't want a top-down motion — we want to invest in community and bottoms-up events. How do you quantify that? It's the right thing from intuition and a business perspective; we have conviction. But quantifying the revenue impact is really hard. So you need conviction on the bets and problem areas to execute, while reviewing pacing bi-weekly or monthly. Some areas — the growth side, pipeline — are much easier to quantify, and there you should be focused on hitting the numbers.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
But people get bogged down there and forget how buyers actually decide to buy software. You know Clay because you saw a lot of people talking about us — not because of some programmatic channel. So what are the inputs that help us be everywhere within the right audience? Those are hard to track, but you have to have conviction. Luckily, our founders really understand the value of brand and content, and how it's different when it comes to attribution. That's the hard part of the CMO–founder relationship: this is the right thing to do, here's why, it's qualitative — are we aligned?
host—JORDAN CHENEVIER-TRUCHET:
It makes me think of Dave Gerhardt — you need to work for a CEO who gets marketing.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Exactly.
host—JORDAN CHENEVIER-TRUCHET:
Since we're on attribution: last year you dropped seven figures on physical billboards. What did the decision process look like, and what was the leading indicator that told you it worked?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
What's maybe different about us on billboards is we don't run them all year. We do a specific window in a specific city where we know there's a strong concentration of our core ICP. The window is late August to early November. A lot of our ICP is in San Francisco then — Dreamforce, SaaStr, the a16z conference, TechCrunch. Everything happens in that timeframe. So how can we add a touch point for people who are already seeing us on LinkedIn?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
In 2024 we did our first billboard campaign, low six figures, same strategy. The problem we needed to solve was the same: how do we show Clay isn't a hacky product? There are channels like billboards where, no matter how big you are, people see you and think “these guys are legit.” You seem like a big company even if you're not.
host—JORDAN CHENEVIER-TRUCHET:
It seems serious.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
So we increased the spend to keep elevating the brand. There are tactics to increase the likelihood of reaching the right person: we mapped all our named accounts in the region — where are their offices — and got the best billboards near them, supplemented with events at the same time, and sponsored those conferences. Everyone who flies in sees us at the airport, on the highway, downtown, at the conference, at our event.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Tracking this is the hardest thing ever. The best way we found is through Gong calls — open opportunities where they mention they saw us there — and we attach the pipeline generated to that campaign. We tried lift studies, but it's really difficult. There's also a secondary benefit: billboards help a lot with recruiting. People see it and think, this company is cool, I want to work there.
host—JORDAN CHENEVIER-TRUCHET:
Our job in marketing is to think about what our actions suggest about us. By doing billboards, you suggest you're big and serious. I always give this example: I'm the co-author of a marketing book. Most marketers haven't read it, but the fact I wrote it means, to some people, I'm a marketing specialist — even if I were a bad marketer.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
It gives you authority.
host—JORDAN CHENEVIER-TRUCHET:
Last questions. What's your focus for the next few months or years? What's the next big thing?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Two things. First, international expansion. Clay naturally has a lot of pull, especially in Europe, with a lot of self-serve customers. How do we build a marketing motion that isn't tone-deaf and resonates with people in different markets — and then as we move into APAC? Second, how do we grow beyond tech? Today Clay is well known inside our bubble — most B2B tech companies know us. But the most legit companies go past tech. Is a random manufacturing company somewhere considering Clay? Getting into those industries is a core question. Those two bets give us step-change growth.
host—JORDAN CHENEVIER-TRUCHET:
Good luck with that — it sounds exciting. Thank you, Bruno. For people who want to get in touch, should we send them to your LinkedIn?
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
LinkedIn is the best place.
host—JORDAN CHENEVIER-TRUCHET:
Thank you again, Bruno, for everything. Keep in touch, and good luck with your next challenges.
guest—BRUNO ESTRELLA—Head of Marketing @ Clay:
Thank you, Jordan. Great to be here.
host—JORDAN CHENEVIER-TRUCHET:
April, there's a big thing happening for you in 2026: you launched the second edition of Obviously Awesome, seven years after the first one. What motivated the rewrite, and what changed in your thinking?
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
A bunch of stuff. The fun thing about doing a second edition is you get to do a do-over. When I launched the original, I assumed it wouldn't sell many copies — I had a very specific audience in mind, mainly B2B technology founders. Then it ended up selling way more than I expected. And when you sell a lot of copies, people send you emails and tell you what you did wrong. After a couple of years you see the pattern: places where I didn't explain myself well, or didn't spend enough time on a concept.
Three things really motivated the rewrite. First: handful of patterns I saw over the six or seven years after the book came out that I didn't fully understand when I wrote the first edition. Second: multi-product positioning. Up until the first edition, the vast majority of companies I worked with had a single product. After the book came out I worked with a lot of multi-product companies, and there are very specific issues there. Third: the process itself. I had broken positioning into five components but ten steps. Tech founders pushed me on that — eventually I realized some of it was pre-work and some post-work, so I rewrote it as five components, five steps, with explicit pre- and post-work around it.
host—JORDAN CHENEVIER-TRUCHET:
For people who haven't read the book — positioning sounds niche but it's everywhere in a business. When is the ideal time to work on it?
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
When we build a product in the first place, we generally have a positioning thesis: assumptions about competitors, differentiation, value, market. We build to that and launch. The first wave of customers either validates or invalidates that thesis. In my experience, the thesis was never 100% correct. Sometimes close, sometimes wildly off. We'd be getting traction in a completely different part of the market with a completely different buyer than we anticipated.
Where I landed: that first wave is the point. In B2B, you usually get those first customers through your network. They're taking a chance on you. Your positioning doesn't have to be razor sharp for that first wave — they're coming through anyway. Once that wave is in, you know where you were right and where you were wrong. Then you can really tighten the positioning. So the perfect time? While you're building, before launch, have a thesis. But don't take that thesis, tighten it up, and put it on the homepage. Keep it loose so you're not closing the door on anybody. Let the market pull you. Once the first wave is validated, then you tighten.
host—JORDAN CHENEVIER-TRUCHET:
You've been vocal that positioning should be revisited in fast-moving markets. Most CMOs treat it like one-and-done at Series A. What signals tell a CMO their positioning is broken?
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
When I ran marketing teams in-house, we did this twice a year. Twice a year doesn't mean we changed the positioning twice a year — it means we got a group together and looked at it. We checked four things:
If the answer is no across all four — don't change the positioning. Simple as that. But if something big happened, assemble the team. Don't just rip it up. Investigate whether you need to adjust.
host—JORDAN CHENEVIER-TRUCHET:
A lot of companies are right now messing with their positioning weekly, mostly because of AI announcements from competitors.
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
If your positioning is working and nothing changed, don't mess with it. When I ran teams, marketing would start changing things mainly because they were bored. I'd come in, find the homepage rewritten, and they'd say "we've been saying this forever, it's boring, everyone knows it." That's a bad reason to change. You're the marketer, you stare at the homepage every day. Your customers don't. Often the team gets bored at the exact moment the positioning is starting to hit.
Early 2025 I worked with an ITSM company doing close to $100M. We did the exercise: "if you didn't exist, what would the customer do?" The head of product said: "Vibe coding is going to wipe us out. We need Replit, Lovable on that list." Those products had been out two months. So I asked the head of sales: "Do customers actually talk about vibe coding? Has anyone said 'maybe I'll vibe code this'?" Head of sales: "Not one." We did the positioning without vibe coding. A year later, I had a check-up call. Vibe coding has blown up everywhere. In their market: still zero losses, still nobody asking. Doesn't mean it'll never happen. Means I don't have to position against a ghost.
host—JORDAN CHENEVIER-TRUCHET:
I see two patterns with my clients. One: competitor changes their homepage and they panic. "If they did it, they're right."
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
There's a lot of bad marketing out there. Just because they're running a campaign or changing their site doesn't mean it's working. Where you actually need to pay attention is sales: are they showing up in deals? An old boss of mine used to say "don't get caught smoking your competitors' marketing." Just because they said it doesn't mean it's anything. They might change it again in two weeks because it's not working.
Look at competitors, sure. But what you see externally is not a reflection of the go-to-market strategy. You don't know their segmentation, where they're getting traction, where they're struggling. You only see it in sales. If they're showing up on shortlists in your deals, take it seriously. Otherwise, marketers get afraid of companies spending a lot on marketing — but lots of companies raise spectacular amounts, blow it on marketing, then flame out two years later.
host—JORDAN CHENEVIER-TRUCHET:
You've said 40 to 60% of B2B deals end in no decision. Most marketing leaders blame sales execution. You blame positioning.
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
Sort of. There's data here. Matt Dixon put out The Jolt Effect a few years back. They studied 2 million sales calls during COVID, then tracked what happened to the deal. Their number was 40 to 60% depending on industry. Roughly 46% of B2B purchase processes end in no decision.
They could also look at why. Sometimes it was "the alternatives look too hard, I'll stick with what I have." But mostly: indecision. Either the solutions all looked the same, or they looked scary. "What if I pick this and it doesn't work? What if I get in trouble with my boss? What if adoption fails?" In a lot of cases the company even says "yes, we picked you, let's go" — and then ghosts you.
If indecision is "they all look the same," that's a positioning failure. Get sharp on differentiated value. But also: the customer needs to feel confident they've done their due diligence, including on competitors. So make it clear "here's what they do, here's what we do, here's when you should pick them vs us." That feels counterintuitive but it builds confidence. Then risk — especially deployment risk in enterprise software. What does professional services look like, training, hands-on after the deal. Sometimes it's packaging and pricing: money-back if not deployed in X months. Sometimes you break the deal into phases: start small, prove yourselves, expand. You take the scary "all at once" off the table.
Often when customers say "price is too high" they really mean "this is too risky." So I don't drop the price, I drop how much they have to commit to right now. I worked at a company selling software to retail stores. Instead of selling 30,000 stores at once, we'd pilot 5, then 100, then region by region. Customer is much more comfortable because nothing goes wildly off the rails on a giant deal.
host—JORDAN CHENEVIER-TRUCHET:
The wall between B2B and B2C feels thinner now — PLG, self-serve, individual buyers. Are they converging?
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
No. Lots of companies have PLG. Fine. But there's a big difference between an enterprise deal and an individual contributor deal. If I sell a $150 widget for a single developer and they slap down a credit card, that's not a complex sale. Low risk. If it doesn't work they buy another one next week. That's closer to B2C. One person, no committee. PLG often looks like that on the front end. Then if a few people in a team start paying, the company comes in over the top and sells an enterprise license. That's a totally different sales process and requires totally different positioning.
On the PLG motion, my positioning is "try it." I'm not running a competitive analysis — I'm getting in front of a person with pain and saying "have a look." On the enterprise side, I'm coming in saying "you should standardize on us." There are teams using other things who may not be happy about that. So I have to articulate the value of going from a few seats to every developer. Different positioning entirely.
Self-serve in enterprise mostly works for two situations: front-end discovery (figure out if there's demand), and cross-sell/upsell after the enterprise deal is closed. Nobody wants to talk to a rep when they're just buying 10 more seats of a database they already own. When I was at IBM, the bar was: under $250K of additional spend on an existing relationship, you weren't allowed to talk to a rep. Different beast.
host—JORDAN CHENEVIER-TRUCHET:
You added a section on multi-product positioning. Most scale-ups I work with have 2-4 products and end up with a Frankenstein: one positioning per product, per persona, per segment.
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
Start with personas, because people overcomplicate this. In a typical B2B deal there are 5 to 11 personas involved. CRM example: head of sales ops is the deal champion. Then security, compliance, end users, IT, economic buyer. When I was a junior product marketer I was taught to do positioning for each persona. We did all that persona work (Marty doesn't like talking on the phone, etc.) and we never used any of it. We never used any of the personas except the champion.
Why? In positioning we are trying to get on a shortlist and get past the first meeting. The champion is the first meeting. The champion makes the shortlist. Our positioning needs to resonate for the champion. The champion might know they have to handle objections from security or end users — we help them handle those. But for everyone else, there's no "value for me." There's only objections. CSO doesn't care about value, they care about "is it SOC 2, are we going to jail." End users care about "do I like using it." That's objection handling, not value positioning. We arm the champion to handle the rest.
Then segments. We don't need separate positioning for retail vs utilities if the value prop is actually the same. We may put different emphasis on different value props in different markets, but the positioning is the same. I worked at a company selling to retail and utilities and the value was the same: business continuity. In utilities, "keep the lights on." In retail, "keep the cash register on." Same positioning. Different customer example in the pitch.
If you're early stage and the positioning really is fundamentally different across two segments, that's usually a sign you need to choose one market. You can't make both happy in the future. Choose.
Now multi-product. Position the way you sell. A division of a big company called me: five products. They wanted positioning across all five. I asked: how do you sell it? They always sold a data warehouse first and then layered analytics tools on top. So position the data warehouse, treat the rest as cross-sell. Another company had five products packaged like a suite — customers picked 3 or 5 or 2, but the mix changed every time. Position the suite: umbrella value. Sometimes it's a single landing product with cross-sell. Sometimes it's a suite. Sometimes it's a portfolio at the IBM scale, with layered positioning at the company, group, and product line level. The question is: what do you want the salesperson to pitch in the first meeting? Position to that.
Salesforce is a good example. For years their ads were "the world's #1 CRM." Land with CRM, cross-sell everything else after: Service Cloud, Marketing Cloud, Slack, Tableau, MuleSoft. Now they're shifting into a more portfolio-style positioning because customers might want to land on Slack or Tableau, not CRM. That shift requires a different kind of positioning conversation.
host—JORDAN CHENEVIER-TRUCHET:
Last big question. Almost every company that IPO'd recently competes in existing categories. They don't create new ones. But every VC-backed startup I talk to wants to create their own category.
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
Category creation is a little bit of magical thinking. Wouldn't it be great if we could invent a name and then dominate because we invented it? If that worked, we'd all be doing it. What does a market category actually do? It tells the customer at a macro level what you're about. It gives them a starting point: who you should be compared to, roughly what you do. It doesn't replace your messaging or your pitch.
Positioning in an existing category is much easier because the customer orients instantly. Snowflake's early line was "a data warehouse for the cloud." We know what a data warehouse is. We know Oracle's data warehouses weren't born in the cloud, so we assume something special here for cloud workloads. Elegant. Easy. If I come in and say "I'm a flim-flommer," now I have to spend 20 minutes explaining what a flim-flommer is before I even start positioning.
There are very few examples of small companies that set out to create a category and then dominated it. Categories do emerge — especially in AI right now — but emergence isn't the same as a single company "inventing" a category. And historically the company doing the hard work of creating the category often doesn't survive to own it. We're not on MySpace, we're on Facebook. We're not using Ask Jeeves, we're using Google. We're not on BlackBerry, we're on iPhone.
Marketers also do wiggly semantics. A company told me "we created a brand new category." Me: "What is it?" Them: "CRM for lawyers." That's a CRM. That's a niche. A subcategory at best. You didn't invent CRMs. Where category creation actually works is when you're already very big and dominant in your existing category and you want to expand the borders. Then you redefine the market you already own to be a bigger market.
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
Then investor vs customer positioning. If you have a SaaS product, your investors may be worried that 10 years from now people will vibe-code it. That's a fair worry. Your investor positioning may need to address it. But that doesn't mean your customer positioning has to. None of your customers want to vibe-code it. None of them are asking. You sell to them on what they care about today. The investor wants a 10-year story. The customer is buying today's dollar for today's outcome. Big difference.
The trap I see in workshops: the founder has been pitching investors for three months. They've been told over and over "what about vibe coding, what about category, what about the 10-year story." Then they're back at the office and that anxiety leaks into the customer pitch. It's natural. The job is to consciously hold the two apart. It is perfectly okay for the investor positioning to be very different from the customer positioning.
host—JORDAN CHENEVIER-TRUCHET:
Where do we send people who want to follow your work?
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
aprildunford.com. Best place to start is the books: Obviously Awesome, brand new 2026 edition. Then if you want to go deeper there's a newsletter, a podcast, and a bunch of other stuff. All linked from the site.
host—JORDAN CHENEVIER-TRUCHET:
Perfect. Thank you, April.
guest—APRIL DUNFORD—Founder @ Ambient Strategy:
Thanks so much for having me.
host—JORDAN CHENEVIER-TRUCHET:
Hey Kieran, welcome to the show.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Hey, thanks for having me on. Excited to be on.
host—JORDAN CHENEVIER-TRUCHET:
Kieran, I think we have a lot to talk about today, but mostly around AI — because you've been quite loud on AI, the way you use it, your thoughts on it. I really want to dedicate this episode to that. What's interesting in your case is that you have the two levels: the strategic one (AI marketing leader), and the operator side. Especially coming from your background as a software engineer. You were a software engineer, correct?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Yeah, I was a failed software engineer. I did computer science at university, did some years coding — Linux, Unix, Perl, Python. Going back to the command line through Claude Code has actually been great for me. I love working through the command line.
host—JORDAN CHENEVIER-TRUCHET:
You've said publicly that AI is killing the middle tier in marketing organizations — people who aren't exceptional craftspeople or highly technical. The thing is, most CMOs and VPs of Marketing have built their org around exactly that middle: headcount, job levels, team design. So how should they consider changing the marketing organization?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
I was speaking to a founder recently who uses a lot of agents in his business. His take is probably right for where we are today: if you have someone who's mediocre at their job, agents can take that work and do it just as well. They cannot do the work of a true craftsperson, a real domain expert. Maybe over time they will, but that's where we are today.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
How does it apply to marketing? What happens in all organizations is that we flatten the org structure — people become much more autonomous and can do much more work because of AI. Marketing is unique among go-to-market teams. In sales, sellers all have pretty much the same role. SDRs, BDRs, AEs — same with customer success, support, even engineering. Marketing has a whole slew of niche teams: product marketers, brand marketers, demand marketers — all with their own domain expertise but not really cross-functional.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
What I think happens because of AI: you'll have more generalists who can do all of marketing, with agents and AI as part of their team. The org gets flatter. Probably less middle managers. People managing many more individual contributors. Those individual contributors will be generalists with agents and assistants helping them across all facets of marketing. And that's already happening — spend any time with AI-native companies, that's how they're set up. Not like traditional marketing teams in tech.
host—JORDAN CHENEVIER-TRUCHET:
For most marketing leaders, they ask their team to adopt AI to be more productive — but people internally start to wonder, "am I just training AI to replace me?" How do you manage that tension?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
There's always going to be a world where you need to have great taste. The most dangerous employee within any organization right now is someone with a small amount of domain expertise and a high amount of AI agency. They're not very good at their job, but they're really passionate and shipping a lot of AI work. They're the most dangerous people in any organization, because they're creating a real amount of slop.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
We're really in the messy middle right now. AI has given people superpowers — they can ship code, ship memos, ship an infinite amount of stuff. But without real domain expertise and understanding why you're using AI, what outcome you're trying to drive, it just creates more and more noise. Everything looks like an AI problem: "I'll use AI for this, ship more of that." But are you really driving more outcomes? Are you really making the business more successful?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
The best people in a company are the people who have real taste, real domain expertise, and high AI agency. They're the ones creating most of the momentum today. As for the question "am I training AI to replace me" — AI is more on personal accountability than the company telling you to do something. It's your choice to make. AI is going to happen whether any of us like it or not. We have very little control over it. So all you can do is try to make the best choices to be the best version of yourself in a world where AI is prevalent.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
What I'd be thinking about: in a world where AI and agents augment what I do, what is the real skill, the real craft, the real domain expertise I can bring to make myself valuable? And one more thing: model capabilities are moving really rapidly, but integration into how companies work is moving really slowly. There's a lot of opportunity to be the one who figures out how to integrate AI into your team, into your business. That's a skill set most companies need.
host—JORDAN CHENEVIER-TRUCHET:
You've said AI projects live or die on data quality. You shared that at HubSpot you had an AI personalization workflow for booking meetings, and it took 3-6 months to get the prompt right. Most B2B companies have fragmented data, messy CRM. What's the minimum viable data foundation?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Every time we've improved the quality of our data feeding the AI to personalize emails, chat, anything — the increases in conversion rate have been pretty startling. Every time we integrate a new dataset and unlock more personalization, we see a 3 to 500% increase in conversion rates on email, which has been around forever. The minimal viable version is whatever you need to elevate your AI experience above the average in your industry. Data sources depend on the vertical and your customer.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
You want a data repository with clean, enriched data the AI can easily use. The example you mentioned was AI prospecting — we've done that all the way through the funnel. AI has taken over a lot of our prospecting and we've seen huge results. Each time we've given the AI a better dataset — internal CRM data, external from various sources — we continue to see real performance increases.
host—JORDAN CHENEVIER-TRUCHET:
You mentioned earlier that measuring AI in software engineering is easy — you have lines of code, you can correlate that to productivity. In marketing, it's harder. What do you follow to see you're on the right track with AI?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
It's a good question. I don't think we've come up with a de facto way to measure all the different teams. We do show-and-tells, we have a singular Slack channel where people post what they're doing with AI integrated across go-to-market. There are three different ways AI usage shows up: my personal usage, my team usage, and how I integrate it into the customer experience. We measure a lot on the customer experience — AI prospecting, sales agents, support agents, success agents — based on business performance.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
The harder one is visual usage. If a product marketer is using AI, what should we expect in terms of output? Five positioning statements per month vs twenty? It doesn't make sense. This is why I think if you're going to lead teams through this next iteration — and you're best in marketing — you have to be an AI-native leader. There's so much nuance in understanding why and how your team is using AI, whether it's driving the right outcomes. There's no clean metric. You yourself have to really understand AI, dig into the details, and provide good feedback. Marketing more than probably any role should have leaders who are quite AI-native, probably in the weeds doing a lot of stuff themselves.
host—JORDAN CHENEVIER-TRUCHET:
How do you make sure when you recruit people that they're already using AI the right way?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
You can give people tasks, and you make the task pretty impossible unless they actually understand how to use AI. In the past, you'd hire a product marketer with a positioning statement exercise. Now you can say "rebuild the website" as part of the task. That's a really easy thing to do with AI. And if they rebuild the website, you see how they bring positioning to life across pages.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
You can give tasks that are a forcing function — if you don't know how to use AI for this task, you'll think it's an incredibly impossible thing to do. Within the interview process, you can also talk to someone and understand whether they use AI. It's not something you can fabricate if the person on the other end actually knows how to use AI. So: the test you give, the interview process, and the portfolio of work — show me real examples of problems you've solved, times where you had high agency and used AI to solve problems traditionally handed off to others.
host—JORDAN CHENEVIER-TRUCHET:
You've said creator-led channels are becoming the dominant B2B brand asset. But most B2B companies don't have a Kieran Flanagan at the top — their executives are cautious about going public. What should they do?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Setup: in 2021 we bought The Hustle. We thought B2B would look like B2C over time — usually B2B is 3-5 years behind B2C. Back then, B2C attention was shifting into creators and individuals. Branded channels like paid CAC were going up. Blogs were getting disrupted by AI. The channels growing were personality-led — YouTube, newsletter, TikTok, Instagram — where the person is at the forefront. We weren't really thinking about AI back in 2021. We bought The Hustle and built a media network — podcast, YouTube, all assets led by people versus brand, but part of the HubSpot network.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
That's been accelerated with AI. People want to connect with people because they trust people, and a lot of branded content gets lost in the AI ether. There's just so much content out there. We're seeing that happen in B2B today. Your question — can every company do this if they don't have a good creator within the org? It depends on the vertical and the customer.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Here's what I think will happen: most brands will have an "AI mascot." That AI mascot will be the face of their brand. An avatar — a synthetic — and people may hate this, but it will be a synthetic avatar that looks very lifelike. It will bring your brand to life across these personality channels. Your content team is the brains behind that mascot. You might think that's a wild idea — it's already happening in B2C. A lot of the biggest Instagram accounts and the fastest-growing ones are AI avatars. You can't tell the difference, but they obviously disclose it. Same on X. You always want to disclose it.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Will people consume content from AI? Already proven — they are, whether they know it or not. There was a study released — I think NYT or another large media org — a blind study where they gave people AI content and human content. The AI content won. Humans objectively, when they don't know it's AI, prefer the AI content because it's better than the average human content. Will there be a moment of backlash? Probably. But it's going to happen. Pull ahead three years and I suspect that some of the biggest creators in B2C and B2B will be avatars with teams of humans behind them.
host—JORDAN CHENEVIER-TRUCHET:
Before you started recording, you said showing your day-to-day AI use cases is like asking you to show your day-to-day computer use — hard to even know what to highlight. Can you elaborate?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Early on when I talked about AI on podcasts, people asked: "show me what you do in Claude." Back then, lots of ChatGPT usage. I've migrated most of my usage into Claude. I'd say things like "here's a memo, red team it, give me all the reasons it won't work" — reverse engineering, like Amazon does. Then you fix problems before doing the thing. A lot of strategy work. I had an agent doing first-principles thinking, then frameworks. But over time, the models got so good I don't think about how I'm using it anymore. It's just part of how I work.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
One tip I can give: I have a Claude project for everything I'm working on. Every document, artifact, meeting note goes into that project. I think of them as mini brains. For a project, I have a mini AI brain in a Claude project. I go to Glean (we use it internally), pull all my notes, meeting notes, Slack messages — and feed them to Claude. We've connected to Glean's API so I can say "before you answer, retrieve the latest updates in these docs." Everything I can put in, I put into Claude in that project as a little brain. It helps me work through things in such an expedited way.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Other tips on tools: I built all my decks in Lovable. Recently I did a pitch off internally with a Claude Code-themed presentation styled like a terminal. Lovable lets you create any style. Claude is also good for presentations. NotebookLM is great. Anything using NanoBanana works well. I've passed the part where I have defined workflows. Instead I'm just working on a task and Claude is a partner working on it with me.
host—JORDAN CHENEVIER-TRUCHET:
You generated the deck in Lovable in terminal style — but can you really get these tools to do presentations linked to your brand book?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Yeah. A UX designer did an awesome internal presentation recently for a leadership team. I asked Lovable to copy it for me. One shot. Completely replicated the design. If you give it your brand styles, colors, palette, it can replicate your presentation really well. The reason you might not use Lovable for external conferences is you'd need a PDF. But anywhere you can do something using a website for your presentation, the creativity in Lovable is great.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
One thing I'd push on: should we even be doing things the way we've always done them? All our decks are uniformed, same brand styles and templates. Maybe that's not the way things should be done. AI lets you be creative in ways you couldn't before. What I see a lot of people doing is "how do I get AI to replicate the things we did before?" That's the worst use I see — "enter your domain and we'll replicate your writing style." But your writing style is probably average. Why would you want to replicate it? AI can do a hundred times better than what you do. Why force it to do something that's bad and generic? I don't think people use AI in the right way. They try to do more of what they already do, not elevate what they do.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
We're in the era of show, don't tell. Anytime you can prototype something and show it, it's way better than a presentation. Way better than a memo. Not always doable, but trying to think about how AI can let us do something different — not just replicate what we've done before with AI faster.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Let me show one of the systems I built in Claude Code. The content team works automatically — I give it a content strategy and it creates a certain amount of content each week. Lessons that apply to any model, any chat: this works just as well in Claude desktop.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
The team is split: an onboarding process creates an audience profile, then a writing style. The writing style can be based on anyone — give the team a name and it creates a style. If you're not a great writer, don't tell it to recreate your style. Tell it to elevate your style.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
People say "this is copying others' writing styles." There's a great copyright framework called copywork from the early 1900s — that's how people got really good at copywriting. Before computers, they'd literally take great writers' work and write it out by hand, letter by letter, to get used to the beats of how someone creates great content. Then you enhance with your own style. That's the writing-style step in my system: get a style card as a foundation, then build your own voice on top.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Then research skills. They create a queue, stack-ranked. An agent provides feedback to the queue and constantly improves it. I think of content in modular blocks: a hook, an intro, an enrichment skill, individual skills per platform. The big thing if you're building real systems: it has to have feedback loops. A performance agent scrapes the web, looks at the content created through the system, integrates analytics, and another agent updates the entire system based on learnings.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
An orchestration skill ties everything together. Rather than remembering all the skills, I just say "let's create content" and the orchestration skill knows all the others. It feels like a little app.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
What's it doing? It's connected to X, Perplexity, OpenAI, and Firecrawl (a tool that crawls websites). Audience profiles are based on what works for me on each platform — the system looks at all my Substack posts plus analytics and says "based on that, this is a winning profile." That matters because the research skills then go find ideas that look like the winning formula for each platform.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Lessons for anyone building this kind of thing: (1) Context really matters. The profiles get pre-loaded — the system has context on who it's creating content for. Whether you're doing product marketing, content, anything — context drives quality. (2) Prompts matter — and they're based on your domain expertise. Your ability to tell the system how to complete a task really well is what makes it skillful. (3) Feedback loops. Show the system examples of what you wanted vs what you got. It gets much better when you're clearer about the outcome you want.
host—JORDAN CHENEVIER-TRUCHET:
How long did it take to build this system?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
It's based on an app I launched last year. The prompts behind the system took about 9 months of iteration. Building it inside Claude Code wasn't long — coming from an engineering background, system building feels logical. Claude Code is so quick at building systems. There's a slash-insights command — run it and Claude shows recommendations for improving the project. You can just say "implement these" and it does.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Over time you can ask Claude Code: "based on the system we've built and your improved capabilities, what should I change, what don't I need anymore?" It really helps you simplify. The value I add is domain expertise — how to bring this to life in a real content system that adds real value. Claude can build the skills and scripts. I didn't build any scripts. It built all of them.
host—JORDAN CHENEVIER-TRUCHET:
How clear are you on the destination before involving Claude? Or do you involve Claude in defining the destination?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
I start with an idea of the system, then work with Claude. I always say to Claude "are we aligned?" — that's a great thing to do before it starts working. It does the ideation. In this example, I had a ton of source code from the app and gave it the entire source code: "here's what I have. How can we replicate this into a system?" It extrapolated all the prompts to start building skills. Then it's iteration. I added the content queue because the more research it did, the harder it got to figure out what ideas it had created. I added feedback loops because it wasn't always right — needed guidance.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
I'm rebuilding the YouTube part because YouTube is so different from text. It's involved in the entire process from start to finish — sometimes Claude is the dominant partner taking the lead, sometimes I'm dominant telling it exactly what to do. Not too different from how you work with an engineer.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
How do I use the output? I never copy and paste content. I create ideas enriched with modular blocks — a story, a case study, an authority quote, a counter-argument, a visual hook — and then I rewrite from that. The system is very much built to how I work. Now if I were giving it away, I'd add an onboarding agent that adapts the system to the user. AI is very personal, very nuanced to how you want to work.
host—JORDAN CHENEVIER-TRUCHET:
For people who want to follow you and learn from you, where do we send them?
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
I did a LinkedIn post about my AI content system. I literally said as a joke "you can only get it on my Substack." I now have 40 DMs on LinkedIn saying "AI content system." So stop DMing me — you can get it on my Substack: kieranflanagan.io. And our YouTube channel is Marketing Against the Grain — with my friend Kipp Bodnar. You'll see a lot of this stuff there visually, watching us build it.
host—JORDAN CHENEVIER-TRUCHET:
All right, thanks a lot Kieran. Talk to you soon.
guest—KIERAN FLANAGAN—SVP Marketing, AI & GTM:
Thank you.
host—JORDAN CHENEVIER-TRUCHET:
Hey Alice, welcome to the show!
guest—ALICE DE COURCY—ex-CMO Cognism:
Hi, thanks for having me.
host—JORDAN CHENEVIER-TRUCHET:
Alice, you're the ex-CMO at Cognism. Can you walk us through your journey at Cognism?
guest—ALICE DE COURCY—ex-CMO Cognism:
I was at Cognism for nearly seven years. I joined when we were just under three million in revenue. When I left, fast approaching the hundred million mark. The team went from three of us in marketing when I joined to about 28 by the end. We acquired a couple of brands during that time. The reason I was brought on: create a predictable, scalable, revenue-generating marketing engine.
guest—ALICE DE COURCY—ex-CMO Cognism:
When you're at zero to one or three to four, you have to find out how good you are at problem-solving with little to no resources. You learn things that traditionally wouldn't fall into your role. You build operational infrastructure from the ground up. You'd never do that at a larger organization, but you have to in those early days.
You get good at unscalable things in early stages because that's what gets success. You operate fairly blind on data. You have to be comfortable acting on directional insights. As you scale, the expectation is you're no longer the bottleneck. You need to give that knowledge to your team.
guest—ALICE DE COURCY—ex-CMO Cognism:
Don't have unrealistic expectations — this doesn't happen overnight. The way I thought about it: every year I was reinterviewing for my job. Whether Head of Marketing or CMO, every year I needed to re-interview for the role. Nobody told me. It was just my mentality, because I had never done that next phase.
guest—ALICE DE COURCY—ex-CMO Cognism:
I worked out what mattered to the CEO. I know something matters to James when he's mentioned it multiple times in the same time period of a day. Not within a week — within the same time period. That meant: prioritize getting an answer.
I worked out how he wanted to be communicated with. He was a founder-CEO operating at high intensity. When he asks me a question, give him an answer in the moment. That was where I needed to meet him. Always have the numbers — if he needs an answer, it's because there's a board member or investor.
guest—ALICE DE COURCY—ex-CMO Cognism:
I wasn't great at this in the early years: be super proactive distilling down what marketing was doing and how it led to growth. Don't be afraid of repetition. Repetition is what builds memory. The more I proactively communicated marketing's role and wins that mattered strategically, the better. He wasn't going to come and ask. It had to come from me.
guest—ALICE DE COURCY—ex-CMO Cognism:
I was big on: don't hire to hire. I needed something to break before I'd hire. We were resource-constrained. I wasn't hiring for tenure. I was hiring for attitude and ability to understand the new playbook.
I had a core belief about what kind of marketing organization I wanted. People are a good or bad fit for that quickly. We trained up generalists. As we scaled, they became specialist where the data showed we should invest.
guest—ALICE DE COURCY—ex-CMO Cognism:
Paid acquisition function. Demand generation — my business unit owners, owning targets per region or segment. Other parts of marketing acted as mini specialist agencies to them. Content and SEO split: SEO for capturing demand, content for the demand creation media engine. Customer marketing and product marketing under the same VP layer. Enablement team — video, website, design — a resource across the org. And an incredible project manager who kept everything cross-departmental on track.
guest—ALICE DE COURCY—ex-CMO Cognism:
Two categories of mistakes. First: when to in-house, when to outsource. We had a growth-at-all-costs era — just threw people at problems. The problem: you can only keep quality of hires to a certain level when your team is a certain size. At too large a scale, you make sacrifices.
Two examples: paid and SEO. I wanted all the experience and domain expertise in-house. The cost of managing that number of people — ensuring career pathways, work variety — it can't happen at scale efficiently. There's a ton of execution work that's really boring. AI is taking a lot of that away.
Specialist in-house plus an agency or AI for execution. That's where I ended up. Had AI been where it is today, that would have happened sooner.
guest—ALICE DE COURCY—ex-CMO Cognism:
Second mistake: senior hires. My philosophy was to grow people. That got challenged as the C-suite tenure changed. I tried hiring much higher experience levels. The promised land: it'll be better, you'll manage less, you'll learn from someone better at that domain.
A good example: product marketing. We tried a couple — with no success. Never lived up to expectations or cost.
Just because someone has tenure on their CV does not mean they'll best execute that role. Done at scale, it's detrimental to culture. People see they're hired over with the promise of learning from someone more experienced — if that value isn't delivered, it's an additional layer between you and the work. Career blocker.
host—JORDAN CHENEVIER-TRUCHET:
When does it make sense to hire someone with 10+ years from a big company?
guest—ALICE DE COURCY—ex-CMO Cognism:
I wouldn't. The only exception: someone who went to a build-phase company, stayed two to three years, succeeded, then went back into building. Hiring someone from that enterprise type and putting them into a build phase — if they haven't been in build phase for 10 years — is never going to be successful. Differentiate the manager versus the builder.
guest—ALICE DE COURCY—ex-CMO Cognism:
Too hands-off for too long. CEOs say to me weekly: "I just want to get some stuff done. Get into execution mode." That's a critical piece marketers shy away from — the execution work. People are scared to hire marketing leaders because all they think they'll get is a positioning statement, not something that moves the engine.
Set expectations upfront with the CEO. It's not about buying hours — you should be buying an output. I should be delivering a product that helps your business move forward.
guest—ALICE DE COURCY—ex-CMO Cognism:
I was a full-on advocate of ebooks and gated content. We were the best at it. Then we hit another phase of growth. I split the funnel: declared intent demo requests on one side, content leads on the other.
I needed 25 demo requests to close 1 deal versus 100 content leads to close 1 deal. ACV decay on content leads — half the ACV. Look at next year's targets, think about budget and resources — not just on marketing, on sales to follow up — the math doesn't math. Unscalable.
I knew the first question was: "can't we just do more demo requests?" Yes, but how scalably? That came from building an engaging, authoritative content engine — always on, all the time, to everyone in our ICP, delivering differentiated value. I couldn't do that AND gate content.
guest—ALICE DE COURCY—ex-CMO Cognism:
I asked the C-suite, "how do you buy?" When you see an ebook, do you give your real personal details? You know it's coming — a PDF in your inbox. Does it actually get read? You know you'll get cold-called from an SDR. The answer was always no, no, no.
It's hard to go against the logic that this isn't the reality. The math, the reality, plus surfacing that sales are aligned — those three things generated buy-in.
host—JORDAN CHENEVIER-TRUCHET:
How do you make the math math?
guest—ALICE DE COURCY—ex-CMO Cognism:
Not cold turkey. Turn down the most inefficient content campaigns. Repurpose that money into ungated. Hypothesis showing how I'll scale demo requests in line with the spend that fills the gap.
The terrible conversion rates on content leads worked in my favor — I didn't need many more demo requests to fill the gap. Within two months I had correlation graphs of spend and demo request increase. As you scale, you invest in software — Fibula on LinkedIn ads, Dream Data across the journey. Eventually proper marketing mix modeling at €100M+.
guest—ALICE DE COURCY—ex-CMO Cognism:
You need a strategy. Topics you want to be known for. Memorability is built through repeatability. Random acts of content, even ungated, won't have impact. Four content buckets:
And distribution. Understand where your audience hangs out and what formats work for those channels.
You cannot cheat quality. We're never going to be as big as competitors on spend. But we can create truly authentic, free quality content that an LLM can't write and competitors can't do at their scale.
guest—ALICE DE COURCY—ex-CMO Cognism:
Strategic reason for the acquisition drives everything. Take Caspr — incredible brand presence in France and we were going into France. We weren't going to kill the brand. PLG motion versus our sales-led motion — we didn't want to cannibalize our SMB audience. Different brand for that reason.
On the back end, fully integrated. Same office, same systems, integrated teams. The Caspr marketers became the French leads.
host—JORDAN CHENEVIER-TRUCHET:
You wrote two books. Give me the sales pitch.
guest—ALICE DE COURCY—ex-CMO Cognism:
The honest ramblings of someone trying to master the CMO role for the first time. A story of two halves — early growth versus later stage are different. The journey from a content lead generation business into a fully bespoke create-demand motion. Anyone in a leadership role for the first time, or building from the beginnings.
host—JORDAN CHENEVIER-TRUCHET:
Where can people reach out?
guest—ALICE DE COURCY—ex-CMO Cognism:
LinkedIn. I'm very active. Put the bell on the LinkedIn posts.
host—JORDAN CHENEVIER-TRUCHET:
Thank you Alice.
guest—ALICE DE COURCY—ex-CMO Cognism:
Thank you.
host—JORDAN CHENEVIER-TRUCHET:
Hey Dave, welcome to the show!
guest—DAVE GERHARDT—Founder Exit Five:
Thanks for having me, Jordan.
host—JORDAN CHENEVIER-TRUCHET:
Now everybody's talking about AI. CMOs and VPs of Marketing are scared. There's huge FOMO. The CEO and the board are pushing "how do we double revenue and divide the team by three with AI and agents?" On your side, you talk a lot about events, social, organic, storytelling. What's wrong with you?
guest—DAVE GERHARDT—Founder Exit Five:
I'm not an engineer. This is the perfect time if you came up to marketing from being an engineer. My friend Tom Wentworth, CMO at Incident IO, posts every day about things he's building with Claude Code. He has engineering background — perfect for this era.
I run a community of B2B marketing professionals — CMOs and marketing leaders. There's a huge gap between what you see on YouTube and what's actually happening inside companies. If you go to YouTube and type "Claude marketing," you'll see 20 videos: "I replaced my marketing team with Claude Code in 20 minutes." Then the next one says 16 minutes. There's a huge cash grab and attention grab.
I'm at the intersection of "I believe in AI" but I also talk to lots of people every week who'd be surprised how many people aren't even using Claude regularly. Just using Claude is a revelation for them.
And ultimately, you're still selling to people. Until my AI agent does research for me and buys on my behalf, exclusively talking to your AI agent, humans are still in the buying process. There's a lot in social, community, and events that pays towards humans.
host—JORDAN CHENEVIER-TRUCHET:
Do you use AI?
guest—DAVE GERHARDT—Founder Exit Five:
Absolutely, of course. I am AI. Claude was actually trained on me.
guest—DAVE GERHARDT—Founder Exit Five:
A lot of stuff that can be replaced makes sense. Advertising is a perfect example. It's always been about how many landing page variations, copy, creative, headlines, images you can produce. Ad creation, landing page creation, automating ads — the future is: I should just be able to go to LinkedIn, type in plain text "show these ads to these people," and it just happens automatically.
But on the other end, we just came back from doing this event with 100 people in Arizona for B2B CMOs. Highly curated, lots of offline time, real conversations. There's something about that human in-person connection.
We're not all going extinct in the next couple years. There's a fundamental need to still want to connect. Content creators are filming videos with old-school video cameras. iPods are back. Landline phones are back. People are dying for a phone with no screen, doing retreats, "raw-dogging" a flight. We're trying to find ways to reconnect, be human, be present.
I want to be in both camps — believe in AI, use it to run my business, but not lose sight of humans being connected over the campfire, telling stories.
guest—DAVE GERHARDT—Founder Exit Five:
I became a CMO because I was good at marketing. You get promoted, eventually rise to the top, and "congratulations, you're good at marketing — you now manage the whole marketing team." Turns out when you do that, you don't actually do a lot of marketing. You do people management, budgets. Most of my day was with HR, the CFO, the CEO, fundraising. I was like, "man, I just like writing copy on a landing page and making an ad."
What's so cool now: I can have an idea — I'm not a designer, I'm not a developer, I only know basic HTML — but I could go this afternoon and build my own website. The speed at which we can go from having an idea to making something is exciting.
host—JORDAN CHENEVIER-TRUCHET:
You had to start from scratch when you left Drift and Privy. How did you handle that?
guest—DAVE GERHARDT—Founder Exit Five:
I never felt like I went from scratch. When I was doing marketing at Drift and Privy, I started writing about marketing on LinkedIn. I had a podcast and a newsletter. Tale as old as time: if you write about the things you're doing online, you attract the audience of like-minded people.
That led to me unintentionally building a large following on LinkedIn of B2B marketers. It wasn't because I wanted to be famous or have a personal brand. I live in the woods in Vermont. I don't drive fancy cars. I'm never going to be the personal brand guy in front of a Lamborghini.
guest—DAVE GERHARDT—Founder Exit Five:
Then it was natural progression — "I have a lot of followers, I'm going to launch a paid version." The closest comparison now would be Substack. Back then it was Patreon. $10 a month. People today are like "Patreon? What the hell is a Patreon? Are you making porn?"
Three to six months in I had a thousand members. That was $10,000 a month in recurring revenue from content. That broke my brain because forever in my mind, $100K in a year was the epitome of success.
That was while I was a CMO. COVID happened, I was home every day. I built that while still CMO at Privy. I had product-market fit before going full-time. My career has just been stacking things on top of each other.
host—JORDAN CHENEVIER-TRUCHET:
Most B2B communities are like dead Slack groups. What did you do to make Exit Five work?
guest—DAVE GERHARDT—Founder Exit Five:
A lot of communities go to zero. They let them get over-riddled with spam and promotional stuff. One way we solve for that early on is by charging money. People thought I was just an awful arrogant evil capitalist. But money is an amazing forcing function to get commitment. We just did our event in Arizona. The two pieces of negative feedback were from the two people who had free tickets.
guest—DAVE GERHARDT—Founder Exit Five:
Number one, we charge from the beginning. Number two, having a really focused niche — exclusively for B2B marketers.
Number three: I've written maybe 8,000 posts all-time and 40,000 comments. For the first five years, I'm in there every day — writing, commenting, policing comments. If Jordan writes a lazy post, I'm like "Hey Jordan, update your post — it's not very specific." Or "this is clearly you promoting your company." Founder mode. Things that don't scale.
Communities mostly die because they're an acquisition channel, not the product. If a vendor owns it and the goal is nurturing people into a SaaS subscription, engagement drops. Every time. Exit Five isn't owned by a vendor. The community IS the product.
guest—DAVE GERHARDT—Founder Exit Five:
It's hard. It's almost like a friend who just has a way. The "je ne sais quoi." You can't go to ChatGPT or Claude and study a storytelling structure and just print it out. The people that are really good at marketing have a wide range of interests outside work.
Especially in B2B: "let's go see how Stripe does their website." Where I'm like "shoot, check this out — this lady down the street has an amazing sandwich shop here in Vermont and her website is awesome." The confidence to not just copy what's been done in your industry.
guest—DAVE GERHARDT—Founder Exit Five:
I have a newsletter — exit5.com/newsletter. I use Claude to write it. It takes 2+ hours.
I'm the subject matter expert. I didn't just give it to AI and one-shot it. It's: "I have this idea. I recorded a podcast with Jordan. Here's the transcript. Here's two other things I've written that relate to this." That's where Claude is amazing — like having a creative agency partner. I'm now piecing each section together.
It's not saving me time. It's making the output better.
host—JORDAN CHENEVIER-TRUCHET:
How do you manage the tension between writing for the company versus writing for you?
guest—DAVE GERHARDT—Founder Exit Five:
It's easy for me — I run the business. But say you're VP of Marketing at a cybersecurity company. You can't write the same way. Get direct with the subject matter expert. People buy from people. The opportunity is sprinkling in personality and being you. Every business is in the business of social media now.
guest—DAVE GERHARDT—Founder Exit Five:
I do look at data. Revenue. Money. Goal: make more than you spend. Indicators: growth in membership, churn. Churn is a killer. Email list growth, engagement, opens, clicks. NPS — are people happy with the thing they're paying for?
In B2B inside a company, MQLs are bullshit. But I run a media company — those ARE our metrics.
host—JORDAN CHENEVIER-TRUCHET:
Do you work on attribution?
guest—DAVE GERHARDT—Founder Exit Five:
Fuck no. We ask every person joining: "how did you hear about us?" They tell us. We export them a couple times a year. We don't learn that much. It reaffirms what we're doing is working.
So much of this comes from over-metricing marketing. At some point you've seen the whole game and you just know — if you do the right things, people will show up.
host—JORDAN CHENEVIER-TRUCHET:
So you don't think about the ROI of content.
guest—DAVE GERHARDT—Founder Exit Five:
Hell no. If we put out good content people like, they will join our newsletter, they will be on our podcasts, they make us look good. If people think we're legit, they will. They're not morons.
host—JORDAN CHENEVIER-TRUCHET:
Where should we send people?
guest—DAVE GERHARDT—Founder Exit Five:
exit5.com is good. Also I'm on LinkedIn — Dave Gerhardt.
host—JORDAN CHENEVIER-TRUCHET:
Thanks Dave.
guest—DAVE GERHARDT—Founder Exit Five:
Thanks for having me.
host—JORDAN CHENEVIER-TRUCHET:
Hey, Eli!
guest—ELI SCHWARTZ—Author Product-Led SEO:
Bonjour Jordan, good to be here.
host—JORDAN CHENEVIER-TRUCHET:
Thank you for being on the pod. For people who don't know you, you're famous for having written a bestseller in the SEO space called Product-Led SEO. What is Product-Led SEO?
guest—ELI SCHWARTZ—Author Product-Led SEO:
The story is: I was working at SurveyMonkey — my last full-time job — and I started consulting on the side. A large brand reached out to potentially hire me. I gave them an offer and they asked: "So what are you going to do for us? Write content? Do keyword research on SEMrush or Ahrefs? Recommend links to build?" I said yes to all three.
Then he asked: "Why wouldn't I hire someone in the Philippines, Pakistan, Bangladesh, or anyone on Fiverr to do that?" I knew the answer was: I'm better. You reached out. You wanted to hire me. If you thought you could do it for $50 on Fiverr, you would have.
I didn't have the concrete answer at the time, and I didn't sign that client. But it forced me to think back on how I did things at SurveyMonkey. The way I did things was not just creating keyword-driven content and building links to it. I thought about what the user was searching for and built that asset. I needed a name for it — Product-Led SEO became the name.
What it really is: when someone is searching, they're not searching for something that matches a keyword. If someone searches "best mobile phone for me," they're not looking for a piece of content that says "best mobile phone for me" 60 times. They want the answer. They want a product. Product-Led SEO is building the thing — a piece of content, a video, an experience — that satisfies the answer, not just matches a keyword.
guest—ELI SCHWARTZ—Author Product-Led SEO:
TripAdvisor is a great example. When someone searches "review of the Ritz Carlton Paris," they're not looking for content that has the phrase "review of Ritz Carlton Paris" 60 times. They want the review. TripAdvisor's approach back then wasn't to write blog post after blog post. They built a website that satisfies any combination — Paris, New York, Ritz Carlton, Hilton. That's the product.
Same with Amazon. They didn't approach e-commerce the way late-90s competitors did — "let's make a piece of content about what a cell phone is." Amazon put all the effort into building the architecture and structure of great SEO. There are now millions of things sold on Amazon that were never dreamed about when Amazon was created — but they don't need to build a new Amazon for each. They extend the architecture. Even better, they took amazon.com and extended it to amazon.fr without needing a new SEO strategy for France.
host—JORDAN CHENEVIER-TRUCHET:
Would you say "product" is an umbrella word that includes content, reviews, calculators, etc.?
guest—ELI SCHWARTZ—Author Product-Led SEO:
It includes the thing the user is looking for. On a media site, content is the product. On an e-commerce site, the e-commerce landing page is the product. On a research page, it's the ideas. Product-Led SEO is really better defined by what it is not: content-led SEO — keyword research, create something that matches exactly what the user searches, call it a day.
host—JORDAN CHENEVIER-TRUCHET:
Between when you wrote the book and today, a big thing happened: LLMs, AI, AI Overviews on Google. What would you rewrite today?
guest—ELI SCHWARTZ—Author Product-Led SEO:
A lot of my book was intended never to be obsolete. I wrote the whole book myself — I didn't hire a ghostwriter. Every time I used "Google," I added "Bing," just in case Bing would overtake Google one day. I didn't talk about a lot of tactics, again because I didn't want it to be obsolete.
Much of the book applies today. The big thing I'd change: I'd talk about AI being an answer itself. AI Overviews, Gemini, ChatGPT — they become that first-layer product. If a user is just looking for an answer, they no longer need a website that has done SEO.
The other part: I'm excited my vision for Product-Led SEO is now coming into fruition. The shady tactics — buying 80 million backlinks, spamming keywords — don't work as much anymore. What's left is essentially Product-Led SEO. The only thing I'd add: help the reader understand that experience also happens on an LLM, and you can't recreate it if it's happening there.
host—JORDAN CHENEVIER-TRUCHET:
Would you advise these big LLM corporations to invest in SEO?
guest—ELI SCHWARTZ—Author Product-Led SEO:
I believe they already are. Go on LinkedIn — OpenAI, DeepSeek, Perplexity, Anthropic all have growth marketing teams and people with SEO titles.
Contrary to what everyone thinks based on social media — "Google's dead, everyone will use LLMs only" — I don't think that's close to the case. Those companies know that to reach 80–90% of the online world, they have to do it through Google.
Given the antitrust suit in the US, Google maintained its monopoly. Google will dominate consumer search until something completely shifts. Not just because they're good — they have distribution power: Android, Workspace, Chrome. People say "kids aren't using Google anymore." In the US, many kids get their first device from school: a Chromebook. Google's Trojan horse is "here's your new computer, it can only use Chrome."
So those LLM companies know the way to reach online users is through Google and typical SEO.
host—JORDAN CHENEVIER-TRUCHET:
People see this as a shift from search to LLM, but actually the cake is getting bigger. People still use Google — they use Google plus OpenAI plus other LLMs.
guest—ELI SCHWARTZ—Author Product-Led SEO:
Exactly. There are many queries Google wasn't a good solution for. Four years before ChatGPT, everyone said Google was dead because of TikTok. TikTok satisfied an area of search Google couldn't — video restaurant reviews, trip plans.
Now LLMs do things Google couldn't. I was using Gemini to figure out why a door in my house wasn't working. I explained the problem, took a picture of the handle, Gemini gave me an answer. I never could have done that on Google. This is a new area of search. By the end I'll probably need to buy a part — that's when I'll go to Google. The top of funnel didn't even exist before.
host—JORDAN CHENEVIER-TRUCHET:
You've said AI owns top-of-funnel and SEO wins mid-funnel and bottom-funnel — even with AI Overviews expanding into mid-funnel. Where do you draw the line?
guest—ELI SCHWARTZ—Author Product-Led SEO:
First: I'm not sure GEO is a real, separate investment. I'd continue to invest in SEO. Many big websites are going to get themselves in trouble because they think AI is the only future, and they'll make basic SEO mistakes — subdomains vs. subdirectories, technical SEO that should be structured at the start.
Top-of-funnel example: someone wonders if they have a health issue, like anxiety. That belongs to AI Overviews. They describe symptoms, the LLM says "this sounds like anxiety." Many blog posts cover that, but Google's AI Overview takes the top of the page and gives the answer.
I worked with a mental health company. Their solution was therapy, for anxiety. There are many ways to address anxiety: meditate, listen to music, take drugs, go to therapy. But this company only offered therapy. So bottom-of-funnel was "therapy" or location-based queries. The super top-of-funnel — "anxiety" — doesn't exist for them anymore. AI Overviews handle that. Now AI tells the user "people with feelings like yours could meditate, listen to music, or try therapy." That brings them to mid-funnel: "therapy for anxiety." That's the only place this company can address.
host—JORDAN CHENEVIER-TRUCHET:
The data shows the top SEO results are 80% the top LLM results. So you should still invest in SEO even to appear on LLMs. Agree?
guest—ELI SCHWARTZ—Author Product-Led SEO:
Yes. I talk to so many companies that want me to recommend them for GEO/AEO. Their answer fits two buckets:
Beyond LLMs, AI is trying to think like a human. You can spam citations all you want, but if AI thinks like a human, it also thinks "which of these citations matter?" Most brands that get cited are cited because they're brands. Build a brand users actually like. That's what the engines are looking for.
I asked John Mueller in Zurich whether Google uses any data from Google Maps and Street View. He said of course they do. If you have a restaurant and Street View goes by, Google Maps tells you if a store is busy. If I were an LLM with access to that data, I'd use it to recommend the pizza shop that's always busy at lunch. You can build all the citations you want, but if Google knows no one goes there, it doesn't matter.
host—JORDAN CHENEVIER-TRUCHET:
Are you familiar with the Five Stages of Awareness framework?
guest—ELI SCHWARTZ—Author Product-Led SEO:
Yes.
host—JORDAN CHENEVIER-TRUCHET:
Instead of ToFu/MoFu/BoFu, with the Five Stages you focus on Problem Aware. Problem Aware is "I type my symptoms." I don't know any solutions — I just know my problem. I go to an LLM because everything is foggy. But when I know exactly what I need — Solution Aware, Product Aware, Most Aware — I just go to Google.
guest—ELI SCHWARTZ—Author Product-Led SEO:
Exactly. I had this experience with one of my first consulting clients, Mixpanel. We did all the SEO stuff but none of it converted. Mixpanel is expensive and very sticky. People landing on the content were very early in the journey. The right way: what do we do at this very high point of the funnel to bring them to the next part? Maybe retarget. Maybe a webinar. Not a big purchase.
host—JORDAN CHENEVIER-TRUCHET:
What's one question a CMO should ask GEO agencies?
guest—ELI SCHWARTZ—Author Product-Led SEO:
Start with the assumption that they probably don't know what they're doing. Agencies only selling AIO/AEO/GEO probably don't. If they have a track record of successful clients in SEO and now show how they've adapted to AI, that's more trustworthy.
Same with tools: look at the people who made the tool. Do they have a track record? If they just "found a niche, everything has switched, let's make money while people don't know what's going on" — avoid.
The basics of AI visibility are the same as SEO. So quiz them on traditional SEO. It's the Wild West with AI — everyone's making things up. I see data studies that completely conflict and they're both right because the data is too vast.
host—JORDAN CHENEVIER-TRUCHET:
How do I convince my CEO not to fall into FOMO?
guest—ELI SCHWARTZ—Author Product-Led SEO:
You don't. I find it very difficult to convince people who really believe in something not to do it. If the CEO really believes GEO is the future, fighting creates friction. What I'd do: do it. Focus 10% on GEO and AI visibility, focus 90% on typical SEO. In six months, if you're right, the CEO will say "this seems to be a scam, let's drop it." You can say "I tried to tell you, which is why I didn't put all my eggs in this basket." Now you deserve a bonus.
host—JORDAN CHENEVIER-TRUCHET:
You have $1M as a CMO. Walk me through the decision tree.
guest—ELI SCHWARTZ—Author Product-Led SEO:
I would not spend it on SEO. First, it's very hard to spend $1M in SEO properly. Second, if you don't already have a brand, do brand marketing first. Most companies should do paid before SEO — it's quick feedback on what works, on product-market fit, on what I call search-market fit. Are people even searching for this? If not, your SEO won't work.
host—JORDAN CHENEVIER-TRUCHET:
Search ads, not social ads?
guest—ELI SCHWARTZ—Author Product-Led SEO:
Search ads, yes. I actually like social ads too. I'd do social ads first, then search ads, then SEO. The biggest bang for buck for any startup with $1M is brand. Hire PR agencies. Get the name out. That trickles down into everything else.
host—JORDAN CHENEVIER-TRUCHET:
Should SEO be in the product team?
guest—ELI SCHWARTZ—Author Product-Led SEO:
Ideally yes. The levers for getting things done are better moved within the product team. On a marketing team, you write tickets that go to product, then engineering. On a product team, you and your colleagues all report to the same boss and work on the structural assets directly.
Example: making a CMS decision. At larger companies, marketing has little influence — it's product. My most successful SEO engagement was Tinder. I worked directly for a VP of Growth. We had engineers, marketers, designers in our growth pod. Two years of work, and the impact came because I was in the product team.
host—JORDAN CHENEVIER-TRUCHET:
What's the best org structure?
guest—ELI SCHWARTZ—Author Product-Led SEO:
SEO would be a product manager whose responsibility is SEO. Hub and spoke, with the PM at the center. If you're SEO inside marketing, you become a spoke and lose control.
host—JORDAN CHENEVIER-TRUCHET:
You said link building is overrated and technical SEO is over-indexed. What do you mean?
guest—ELI SCHWARTZ—Author Product-Led SEO:
SEO audits come back with technical feedback — 301 redirects, 302s, 404s. If you implement everything, you're unlikely to see much growth. It's like going to the doctor and being told to run 10 miles a week. Maybe you live longer. Will you meaningfully make more revenue? Most honest consultants would have a hard time saying yes.
On link building: there was a time it really mattered — raw PageRank, no filters. For many years now Google filters that out. I had a backlink from WhiteHouse.gov when I joined SurveyMonkey — the Obama White House did a partnership. The link was a 404. I created a page to fix the 404, then linked from it across the site. All those pages started ranking higher. That was 2012.
In 2018 SurveyMonkey got more White House backlinks — they were scraping our research. None did anything. Why? Google got smarter. The White House is authoritative on government, not on customer feedback surveys. So Google said "this is not a relevant link."
That was 2018. They've gotten even smarter. They look at a Forbes link and say "this is paid placement." So just getting a high-DA link isn't something I'd invest in. Same with citations.
host—JORDAN CHENEVIER-TRUCHET:
How do you see the future of SEO?
guest—ELI SCHWARTZ—Author Product-Led SEO:
SEO never disappears. I made a prediction that Meta is about to launch its own search engine — their LLM already exists at meta.ai. It will work by pulling Meta data — Facebook, Instagram, WhatsApp Business. They've made big AI acquisitions. Real player.
host—JORDAN CHENEVIER-TRUCHET:
They actually announced an acquisition today.
guest—ELI SCHWARTZ—Author Product-Led SEO:
The world of LLMs will be dominated by companies that were already huge. OpenAI raised a lot, but beyond OpenAI and Anthropic, big tech wins. SEO is always this request for discovery. Search 15 years ago was "go on your computer and type into Google." Next year it might be glasses. That's still search.
host—JORDAN CHENEVIER-TRUCHET:
One contrarian take that you believe almost nobody in the industry agrees with you on?
guest—ELI SCHWARTZ—Author Product-Led SEO:
I really don't think anybody should be investing significantly in AI as a separate thing. Invest in search visibility. The way GEO/AEO is framed today is as if it's something separate. It's like 20 years ago when "mobile SEO" became a thing — as if you had an SEO person and a mobile SEO person. Same trap.
AI visibility is just the 2026/2027 version of SEO. Make sure your existing agency knows how to think about SEO of today, which has an AI visibility element. Don't break it off and call it a new thing — that creates a budget category you don't have to spend in.
host—JORDAN CHENEVIER-TRUCHET:
Fair enough. Thank you, Eli. For people who want to follow you, you've got a newsletter and you post on LinkedIn. Your book Product-Led SEO is still a bestseller — link in the description.
guest—ELI SCHWARTZ—Author Product-Led SEO:
LinkedIn is great. And please read my newsletter. I've been doing it for three years. When I started, no one read it. I just wrote to the world. Now I have almost 14,000 subscribers. Whenever someone asks how I got there, I just kept writing. Honored if anyone reads it.
host—JORDAN CHENEVIER-TRUCHET:
I'll put the link in the description. Thank you, Eli, all the best.
guest—ELI SCHWARTZ—Author Product-Led SEO:
Thanks for having me.
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