In this conversation, Pete Crosby (Speaker A) and a co‑host (Speaker B) walk SaaS founders and CEOs through the critical considerations when hiring a Chief Marketing Officer. They begin by describing the typical growth plateaus SaaS companies hit (e.g., $10M, $20M‑$50M ARR) and argue that many of these blocks stem from leaders not knowing what they don’t know. The discussion then pivots to four inter‑related themes: 1. Stage Fit & Velocity – The new CMO must have direct experience at the company’s current revenue stage and must be comfortable with the expected growth velocity (e.g., moving from 10% to 400% YoY). Hiring someone who only knows a slower‑growth, bootstrapped environment can mis‑align expectations. 2. Executive‑Team Alignment – The CMO’s role changes depending on the CEO’s background (founder‑storyteller vs. technical CTO‑CEO) and the composition of the leadership team, especially the head of sales. Fit with these personalities is as important as functional skill. 3. Four Core Marketing Competency Areas – The speakers break the CMO’s impact into product marketing, branded communications, demand generation, and operational/RevOps capability. Most leaders excel in one or two of these; pretending to be strong in all four is a disservice. 4. Evaluation Framework – They suggest a practical matrix: list ~20 points across the four competency buckets, have the candidate score themselves, and have the hiring CEO score the company’s needs. This reveals gaps and alignment. 5. Market Shifts & AI – Emerging AI‑native SaaS businesses demand faster iteration, pricing ownership, and a hands‑on, do‑er mindset from CMOs, moving the role toward direct execution rather than pure strategy. 6. Common Hiring Mistakes – Over‑hiring senior brand marketers at early stages, under‑hiring marketers, and hiring CMOs whose expectations don’t match the company’s support structures are highlighted as frequent pitfalls. Overall, the dialogue equips CEOs with a structured lens to assess CMO candidates, emphasizing stage‑appropriate experience, cultural fit, clear competency focus, and the evolving demands of AI‑driven growth.
Chapters
One of our objectives at Revesco is that we understand that normally founders and CEOs of a SaaS business can normally get their business to, let's say, $10 million in ARR. And at that point, often they reach a block. And then there's like another stage, it might be $20 million, $30 million, $50 million. And it's normally just down to a really simple thing, which is leaders don't know what they don't know. And one of our objectives at Revesco is to help shine a light on what is coming next around the corner at each new level of scale. So can we go through from the role of a CMO, what should that CMO be expected to contribute to the business and how does that change?
So of course there's a whole bunch of things that just change based on market and sector, but let's talk about some generalizations that I think can be useful. Firstly, let's talk about stage fit and the fit of the CMO to the stage, to your question. Then let's also talk about the different, the span of a CMO and where they spike and when that might be needed for different businesses in different stages. And then maybe we can talk about a couple of other things that are changing as we're all adopting AI. So firstly, stage fit. I think it is really critical that as you choose a CMO for your next stage, that they have the experience, not of the place you want to be in several years' time, but they have experience at the stage you're going through right now. I think it's really hard to thrive in an environment where you don't know what good looks like. And so, you know, yes, you can find some fantastic, perhaps one level down leaders that now are ready to shine. and they've been through the experience of that stage, but perhaps not as the kind of number one role. And maybe you've got other people who've been part of a team, who've been on part of that journey. So, you know, I think there are ways of thinking about this other than just, has this person been CMO at this specific revenue journey before? But I think stage fit is really important. I also think, however, that the velocity expectations of the business are important. So if you've been a CMO at $10 million, But the previous business you were working in was bootstrapped and was growing at 10% a year, versus now going into an AI-native business at $10 million, but they expect to be $50 million next year. That's just a radically different job to be done. And so, yes, do they have the experience crossover of a bit of where you are or where you will be next year through the next couple of years? Do they have that velocity experience or alignment over velocity? I also think that One of the questions I like to ask of CMOs that have been at multiple stages is, what made you come alive? Like, where did you get most joy? Because that's gotta be important here too. You do your best work where you experience most joy. And I really think that many of the startups that I've ended up, particularly before I joined Paddle, when I was doing a bunch of fractional roles, a lot of those situations were people who had overhired. and got a big hitter from a big brand who hadn't been at this earlier stage for quite a long time, but was looking to try and be really kind of scrappy. And it just didn't work because the company didn't have all the support structures and the documents and artifacts and resources that they were used to. Or was businesses that had perennially underhired and churned through marketers that the CEO was not happy with because they weren't able to move the needle, often because they weren't able to market as well as the CEO is. Hmm. Which is a kind of a key challenge in those early days when your CEO is, kind of outward facing and perhaps the best marketer in the business by default. And so, yeah, I think stage is one way of looking at it. The other thing is the fit against the other people in the executive team. Because if you've got a founder who is leading the company strategy, leading the company story, speaking at all the conferences, the role of the CMO, particularly in those early days, is radically different than if you've got perhaps a CTO turned CEO who's built the product, who deeply understands the problem space and how you— and the engineering solution. But doesn't gravitate to building that market message. And so you've gotta think about how your fit is against that CEO and perhaps also the head of sales. Mm-hmm. And maybe some other people on the exec team, which then comes on to kind of the third way of evaluating a CMO against the opportunity, which is, I think that, you know, we can talk about different areas, but let's break it down into 4 common ones. I think the role of a marketing leader spikes across 4 different ways. It's product marketing. So can I accurately, compellingly describe the product and the market it serves? And message that in a way and launch? Secondly, branded communications. Can I build that narrative that guides the whole business as well as informs and influences the customer and the market? Thirdly, demand generation. You know, can I build that model, that system of how we go and repeatedly acquire via different channels? And then fourthly, and this perhaps was less prevalent in the past for marketing leaders, but an operational background. So really come in detail understanding the stack and the toolkit and how it all works together and the numbers, that kind of RevOps perspective. And I think as a marketing leader, you are doing yourself and the company a disservice if you pretend to be good at all 4 of those. I think most marketing leaders spike in 1, maybe 2 of those 4. And so then it's about evaluating for the company you are serving and for the stage they are in and what needs to be done. Are you spiking in the areas that are right? And that's just a really helpful process to go through. I think there's different—
Mm-hmm.
People think about this different ways. Often I ask a candidate and then also the person who's trying to hire to, you know, assemble perhaps 20 points along those 4 categories and try not to make them an even 5 on every one of them so that they can explain where they fit and the CEO can explain what their company needs. So you can start evaluating whether there's a good match or not.
What are some of the other things that are changing in the market at the moment?
I think one of the hardest things right now when it comes to hiring marketing leaders, 2 of the hardest things right now. Firstly, The marketing leadership role has always been very broad. It's always covered things all the way, often from internal communications, you know, leading company all-hands and that kind of thing, all the way through to reputation and brand, all the way through to, do we have enough pipeline this week, this month, this quarter, all the way through to sometimes managing BDRs, to definitely managing tech stack, to thinking about quite large budgets across multiple, you know, there's just all this range of surface areas, a more diverse surface area than most of the other executives sit in. And also, A lot of that surface area is easy for others on the executive team to think they have domain knowledge, and certainly have a loud opinion on, right? And so I think it's a really hard role. And so, you know, that aspect, I think, is only getting more complicated now, as we're diving into a world where you now have to be agent-first, and you have to operate at the speed of light. And suddenly monetization becomes more important, because you're not running an 80% SaaS margin. And so you've gotta be the pricing owner, and the margin owner as well. And there's all kinds of things. Product-market fit is becoming a treadmill you have to go through every week rather than something that you achieve and then pass through. There's all these things that make it more complicated and faster moving. I think the second piece, though, is perhaps the more interesting one, and the more definite one. I think in a world gone by, you went from being a specialist in an area, and then you got promoted into management, and management had to become your specialism. And then as you became more senior, kind of your your unit of delivery went from a campaign or a blog post to perhaps a strategy for a channel, to perhaps a multichannel strategy, to perhaps running a team who run a multichannel strategy, to influencing the executive team around resourcing allocation across this system you've built. And now I don't know anyone who's trying to hire a CMO who's not also a doer and doesn't know their way around Claude and doesn't understand how agents can work in a very distributed way. And so they're doing the work rather than the team. And that isn't having to answer questions around why they're hiring new people rather than just giving the work to robots. And so you've suddenly got a world where not only do you have to be experts in the surface area you're operating on, you've gotta be a doer on a whole bunch of areas where perhaps, if you've been in the market for 10, 15 years, you've lost context on, 'cause you've not done that job for 5, 10 years, or perhaps never before. And I think that is a a real opportunity for generalists who have got deep experience in a certain market or a certain process or area, and now they can use this horizontal context, and it's a real opportunity for people who love to get their hands dirty.
