How Top AI CEOs Hire Their Executive Teams

Keith Cowing
This is Executives Unplugged. I'm Keith Cowing, your host and executive coach. And today I'm in New York City with Michael Cullen. Michael is an executive recruiter and the founder of Bleecker Street, where he works with top AI CEOs to hire their executive teams. The old hiring playbooks are getting thrown out. Roles are merging. Resumes mean less than they ever have before. The best people have five offers you have to compete with, and Michael's seeing it happen in real time. We get into why your marketing hire should come earlier than you think, what happened after everyone flooded the zone with forward-deployed engineers, the overlooked signal he looks for on resumes, and a whole lot more. Let's jump in.

Keith Cowing
Coming to you here in New York City, the beautiful Kit Studios. I came in on the train this morning. Turns out it's Comic Con in New York. I didn't realize until I got on the train, and I was surrounded by Superman and Batman and Disney princesses and wizards and absolutely immaculate costumes. It's never boring in this city.

Michael Cullen
Yeah, I think that's one of the reasons why New York is such a great place to build. On any given day you've got Comic Con going on, you've got some of the best art in the world, some of the best food in the world. And when you have that, you get these intersections of ideas, intersections of people, some of the most creative people in the world, some of the biggest titans of industry. There's a great quote from David Haber, an a16z investor, about all the opportunity that exists in the overlaps of these industries, and it's one of the reasons he thinks New York is such a great place to build: people don't get stuck in silos or one way of thinking about things. You go to Nashville with healthcare, you go to SF with AI, everyone's beating to the same drum, but New York creates a lot of different opportunities, ideas, intersections.

Keith Cowing
If you had to hire a superhero, who would it be?

Michael Cullen
That's a good one. In a lot of ways, I feel like we're in this Iron Man moment, where with Claude Code and with tools, everyone has this tech-enabled suit around them that can help them fly to the moon or blow up a building or do all these things. And a lot of the way people are building teams now is, we've got to put a bunch of Iron Men in suits, and maybe you don't need as big a team, but you still need that human in the suit. So there's this interesting concept I'm seeing around people really being able to extend their capabilities, but still needing that human in the loop, that person making the decisions on what to do.

Keith Cowing
Superpowers, but a human underneath, learning, adjusting. Which superhero do you think crushes the interview but gets fired in six months?

Michael Cullen
Probably Superman. I feel like he's all brawn, no brains. It's been interesting watching the evolution of superhero movies, and you really can't make a good Superman movie these days, because there's just not a lot of depth to that character. What would come out of the interview would be a lot of great stuff, but as you got into the role you'd realize it's a pretty shallow exec.

Keith Cowing
Well, taking that into more serious stuff: you work with CEOs, they're hiring executives, and the old playbooks are getting thrown out. So let's get specific. A CEO hiring an executive team. Let's talk about sequencing. There used to be a playbook: you hire your head of product at this stage, your head of marketing at that stage, CFO at this stage. What do you see changing?

Michael Cullen
One of the biggest trends, or the advice I'll give clients, is to move marketing higher up, earlier in the sequence. In a world of AI-enabled building, AI-enabled code gen, the ability to copycat features of your competitors, distribution is emerging as a huge moat. So if you can move marketing earlier, get your story out into the market: ultimately people are buying stories, people are buying the idea of something. The actual product is probably secondary. That's going to help you get to market faster, and it's also going to help you on recruiting and talent and fundraising. There are a lot of second-order effects when you secure a great marketing hire early. So I'm always telling people to push that higher up, because everything gets a lot easier once you have your story in place, once your brand is out there. Specifically on recruiting: when you're building that website or that brand story, a lot of the people looking at it are actually not customers, they're prospective employees. And if that's cohesive and looks like a place someone would be proud to work, it's going to make it a lot easier to recruit top talent, beyond the obvious customer benefits.

Keith Cowing
I'm a product person at heart, so I always liked quality product first and then you tell the story. In a world where product's everywhere, you have to break through, and breaking through is about storytelling, about marketing. With companies like Harvey, it seemed like they told the story first. The best product never won on its own, but it seems like that's been accentuated a hundred times over.

Michael Cullen
We're in such a copycat world now. Once someone finds some alpha on the product side, your competitors are just going to release the same thing. Decagon releases a product, Sierra's right behind them; Sierra releases a product, Decagon's right there. You see that with Harvey and Legora. These are superhero clashes of huge vertical AI companies, and the difference is really just: what's the story, what do people know about them, what's the perception of them? Because product features collapse in much faster cycles now than ten, twenty years ago, when if someone had a huge release, it would take the other company a year to catch up if they were truly bleeding edge.

Keith Cowing
We've talked about jobs that are combining. Product and engineering sometimes merging at the exec level, product and marketing, sometimes product and customer success. What are you seeing on which exec roles are combining, and why?

Michael Cullen
AI seems to be the time of the generalists. Knowing a lot about many different things, being able to plug into a lot of different areas, is definitely an advantage. A lot of people really like former founders, people who had to be in that founding CEO seat doing a bunch of different things, but who have a specialist vein that runs through their career. With codegen, with AI-enabled product development, you're seeing all these wacky bedfellows. Customer success and product and engineering collaborating in ways they never would have before. At the most AI-enabled companies in the world you have CSMs pushing code to prod and fixing customer problems the same day. You see that with a Rillet or a Ramp, and it's incredible to see these businesses move at that speed. A lot of that comes from generalist thinking, where a product person is no longer just a product person. They're also commercial, customer-facing, thinking about all these things.

Keith Cowing
How do you test for that? It feels more like it's about mindset and psychology than resume. Resumes were probably always a bad filter, but it's a tool everybody had: you worked at this company, you had this role, great, we should interview that person. Now what do you look for?

Michael Cullen
I just like to have a conversation with people and test and tease and think about different ideas, and see how zeitgeisty they are in terms of what they're talking about, what they're reading, what tools they're using. I wish I could tell you I had three questions and then you find out if that's your product leader or not. But a lot of it is the conversations you're having over time, testing their thinking about how these concepts are evolving, testing their thinking about how to build in this new era. It's more art than science, in my opinion. And there's never been a more interesting time to build a company than right now.

Keith Cowing
Another hot topic: FDEs, forward-deployed engineers. Super hot six to twelve months ago. What's happening now? What's the retro on whether those hires worked? Are people still trying to hire them?

Michael Cullen
Forward-deployed engineer is a term I'd never heard two years ago, and it became a big part of our business in 2025 and into 2026. These tools went from a world where you'd buy Salesforce and hook it up yourself, maybe with a consulting fee to get set up, but it was really a self-serve product, to now, when you're fundamentally changing how work happens within an enterprise, you need hands on keyboard, touching all the APIs, all the data sources. That requires another level of implementation. So we flooded the zone with forward-deployed engineers and had them run rampant everywhere. I think 2026 into 2027 is about how you organize that into a machine, an engine of actual results. How do we turn this into something repeatable and scalable, that takes us from Series B and C to D, E, and IPO? That's a different question. And you're also seeing pushback from some AI companies saying, if your product is really good enough and truly agentic or best in class, you shouldn't need an army of people to set it up. It should just self-serve and work. So some companies are intentionally anti forward-deployed engineer, trying to stay disciplined enough to build a product. The margins go down. It looks a lot more like a services business than a software business.

Keith Cowing
And you have to be in there forever.

Michael Cullen
I think it's something like a million dollars a year for a Palantir FDE if you're an enterprise trying to buy one of those folks. It's really expensive, and you have to pay those people a lot. FDEs typically don't last past thirty. It's a young person's game. You're on the road a lot, you're in Des Moines, Iowa, setting up technology and servers. It's definitely a strained model. The one tailwind is that about ten years ago everyone told their kids to go get computer science degrees, and a lot of those people got them without really wanting to be full-time coders. So you have a much larger population of twenty-somethings with computer science degrees who don't want to code full time, but who are facile and can problem solve. That consulting class, when I graduated college, was probably studying economics or political science; it's kind of moved into computer science. So there's a larger population that can do it, but it's still a very challenging hire. And real coders don't want to spend time in front of customers. They want to develop software.

Keith Cowing
It's funny on the FDE front. I remember back in 2012 people at Palantir having this job title, and I had no idea what it was. And when I worked in semiconductors in 2004, we had FAEs, field applications engineers. I worked at Cypress Semiconductor; we sold chips to LG and Samsung and Cisco. If Cisco was designing a new network switch, a field applications engineer would be in there helping with the design and how our chip could fit into it. They got paid well. It was the lifeblood of the company.

Michael Cullen
I do think the word "deployed" is a little aggressive. When Palantir did it, they were sending people to the Middle East to sit side by side with soldiers. And it's kind of funny when it's, "we're going to forward-deploy these people to Mercedes."

A note on that too. One of the qualities we've seen work best for those roles is people who were computer science TAs. Having to teach a concept really reinforces the understanding, and it builds the communication skills necessary for the forward-deployed motion. We do a lot of work with Cognition, and if we see someone was a TA at Stanford or MIT, that's a huge green flag.

Keith Cowing
Great pro tip: when you're hiring, look for people who've not only done it, but have taught it.

Michael Cullen
Back to your question of whether the resume matters, that's one thing that really stands out.

Keith Cowing
Teaching is the ultimate form of learning. It requires you to simplify something so you can articulate it to somebody else, which is a superpower.

Michael Cullen
And it means the computer science professors thought they were one of their top students, someone who could teach it.

Keith Cowing
And they probably loved it. Let's talk about adaptability: learning curve and slope rather than experience. People are being asked to do jobs, let's say product and customer success combined, that haven't really been done before. And by the time you hire an exec, in six months the whole company is going to change, the whole world is going to change. You're hiring for what the future might look like. How do you hire for adaptability and learning curve, versus "I worked at this company, I did the thing before, so I'm proven"?

Michael Cullen
A lot of it is: what problems have they solved in the past, and are they similar? There have always been ambiguous problems to solve in business. This idea that we're in a completely new era is a bit overblown. There have been new problems requiring new ways of thinking for a long time. So one thing I like to see is: have they entered a blank-slate, tabula rasa situation and really put pen to paper on an idea, on a structure, and created something where there wasn't something before? If they can do that in some other domain that maybe is now solved, they're ready for the next challenge in this new domain. And you want to see markers of fast success: people continuously taking on bigger and bigger challenges, and moving once there's another big challenge to take on. If someone's been in a manager band for six years straight, there's a signal there that they're not going after that next big challenge. Nothing against them as a person, but it's probably not the slope we need to take on a really ambiguous, sticky problem.

Keith Cowing
What about big company versus growth stage? Hyperscalers versus a Series C company that's scaling. In the past there have been issues with people from big companies coming over, but it feels like there's more back and forth these days with top AI minds. How well does big company experience translate?

Michael Cullen
On an IC level, it's probably pretty transferable. On a management level, it's pretty hard. I've not seen a ton of success with people coming from 10,000-person organizations into startups. It's a different ballgame. Where we can pull from bigger companies is what I call scaled tech: the 10-to-15-year-old companies like Stripe, Databricks, Datadog. In the old-school way they'd have IPO'd; maybe they're Series E. Still founder-run, still have slope to them, but they represent scale. Those are companies we're often pulling from. It's harder to pull from Meta, Google, Apple.

Keith Cowing
Meaning it doesn't translate.

Michael Cullen
It's a different ballgame, a different skill set, a different comp structure, a different pace. For certain roles it can work. For AI researcher roles or software engineers or more junior roles, there's room to translate. But for someone who has to lead a product organization, taking the person who runs the Google Docs edit history window and having them run an entire product org for a startup is very hard to make mesh.

Keith Cowing
One of the things that makes people really successful is conviction and confidence, because you have to make decisions quickly. You also have to have the humility to know you don't have the answers, that you need a lot of input. How do you test for each of those?

Michael Cullen
We have a core value at Bleecker Street called "make a call." Just make a decision. It's not always going to be right, you're not always going to have perfect information, but it's better to make a decision, see what happens, learn from the reaction, and make another decision. You can't be too hard on yourself if the call you made is incorrect. It's: you've made that call, where do you go on the next one, and how do you keep learning and growing? So the key when you're interviewing executives and asking about decisions they made is: do they have the humility to zoom out and say, yeah, it wasn't the best decision, or this was the information we had at the time and we made that decision. That's really all you can do, because no one makes a hundred percent perfect calls. I'd rather work with someone who can make a hundred calls and be fine if ninety are right than someone who makes twenty and nineteen are right. Especially in this day and age, if you're sitting there deliberating, waiting for enough information to come, you're going to be left behind by people who are moving faster and making more reversible decisions than you are.

Keith Cowing
Put us in that room. You're an expert interviewer. Do you look at the resume, pick something out and say, tell me about this decision? Or do you say, tell me about a critical decision you've made? How do you tee up that conversation?

Michael Cullen
I'm fascinated by people who were at a company pre-2022, pre-ChatGPT, and are still there now. I'll often say, walk me through the journey, before and after. I'm listening for narratives and picking apart narratives. My interview style is less question, answer, question, answer. It's more: put them on a narrative they know well, then start asking questions, picking apart the narrative, digging deeper, asking why and how. And through the way they react: how quick on their toes are they, how legitimate is that answer, are they seemingly telling the truth, does it hold water given their whole story? That's what I'm listening for, more than "tell me about a time you made a decision."

Keith Cowing
You find all these things, you've got the perfect candidate. Of course this person is going to have five offers, because it's a hot market for the top people. If you're working with a CEO to close a top executive, how do you get them to win versus the four or five others also hunting them with great companies and great offers?

Michael Cullen
There are two things I really lean on in closing. One is speed. Closing a candidate should feel like sweeping someone off their feet. It should be a romantic action, where every next step is a bigger and more important meeting. Now they're meeting the CEO, now they're meeting the lead investor, now they're getting the offer, now the offer's getting better. It's all momentum. The second people feel the momentum pulling out of the room, it's very hard to get that mojo back. It just goes cold. The flip side, and this is more psychological, is that human beings fundamentally want to belong. Going back to your Comic Con example, people who go to Comic Con have their people. They're wearing the same costumes, they know the same lingo, they feel like they belong. So you want to make that finalist feel like they belong, that this is a company of like-minded people where they'll fit in, even on a middle-school-insecurity level. If you can make someone feel on a tribal level that they're one of us, that's going to psychologically help them make that really hard decision about where to go.

Keith Cowing
I love that. Comic Con is not where I belong. But my son, who's fifteen, went to Fanatics Fest, which is the same thing for sports super fans, and that's where he belonged. It was really fun to see. You've got to find your place. There's a vibe of what I care about, what I'm excited about, how I behave, how I dress, the whole thing. I want to be somewhere I can do my best work and don't have to play a role. How do you get both sides to see when it is a fit?

Michael Cullen
Spending time in person with clients is one of the most important things we do at Bleecker Street as a recruiting firm. Walking the halls, seeing what they do. Are they an in-person, late-night culture? Is the office client-facing and prim and proper? Is it messy, with people playing Super Smash Bros in the conference room? All these little things you see when you physically go somewhere create a whole narrative, a patchwork quilt of what that company is like. You can't get that from a website, you can't get it from a culture doc, and you can't get it from behind a Zoom screen. So as much as we possibly can, we go in. We were at an office the other day and the Wi-Fi password was a clever little pun related to the company. Okay, that tells me they're detail-oriented and thoughtful, every little thing matters. The conference room is neat and ready for, in this case, healthcare executives to come in. That's a different culture than one where people wear sweatpants, and there's nothing better or worse about either, they're just different. And you don't get that from Zoom. You have to go meet these people and do the human element of it all.

Keith Cowing
Speaking of in person: the execs you're recruiting today, how many days a week are they in person? How many are completely virtual?

Michael Cullen
New York and San Francisco are pretty much identical to how they were before the pandemic. There's a little more naming of a remote or flexible day, whereas in the 2000s you'd have just been fine leaving for a wedding on a Friday or taking a day here or there. So it's five days, ish. I think the 996 thing is starting to die, which is good to see. Naming 996 is basically telling people who have kids or partners that they're not welcome. I always laugh at the sales teams who make people come in on Saturdays. Who are they calling on that day?

Keith Cowing
Kind of dumb, right? There are sprints in this game, that's real. But hold your energy back for the real sprints, and don't burn out for no reason when you don't need to.

Michael Cullen
Right. If everything is an emergency, nothing is an emergency. Energy management is huge, and it feels like people are swinging back to that. The performative in the office, not doing anything, super-late-hours stuff is starting to die off, which is good to see.

Keith Cowing
You could build your recruiting firm anywhere. Why build it in New York?

Michael Cullen
It's this intersection of the smartest, most talented, ambitious people from all walks of industry. We have the best, if not the second best, of everything in the world. Maybe we don't have better Japanese food than Japan, but we certainly have the second-best Japanese food in the world, and you see that in every industry, and some industries where we just dominate. I always compare living in New York to working out in a gym where there are Olympic athletes around you. It drives me to work out a lot harder, to be at the top of my game, to push myself, to become a better executive and person. I love the energy and the competitive nature. It's collegial, but that competitive nature flows through the subways here.

Keith Cowing
What a better note to end it on. Thank you for joining me here in New York.

Michael Cullen
Of course. Thank you.