The Truth About Hiring Your First Head of Product

Dennis Crowley: I've always thought that I was more of the product type of CEO. So I can fill in for the head of product for most things. And I did that for a long time at Foursquare before we eventually hired. People to run it. With the project that we're working on now, just because like the tools are so different, we hired a lead product person almost immediately just because I met this woman who was a.

very, very skilled, like really into the product and had worked in stuff in adjacent spaces and was very fluent in like, AI tools and technology. And it's like, not only do you know stuff that I don't, but you know how to work in a way that I don't know how to work.

Keith Cowing: This is Executives Unplugged. I'm Keith Cowing, your host and executive coach, and that was the voice of Dennis Crowley, founder of Foursquare and Hopscotch Labs. Today we're talking about the biggest mistakes that founders and CEOs make when hiring their first VP of product or CPO. Focused on companies in the series A to series C range.

So if you're a product leader or a founder. This is for you. In order to break this down, I went and talked to four of the best in the business, Chris Running Jodi Jefferson, Michael Cullen, all executive recruiters who work with CEOs every day to build out their executive teams. And Dennis Crowley to get that CEO perspective, When A CEO picks up the phone and says, I want to hire a head of product, what is the first question that executive recruiters ask them .

Chris Running: Whenever we're having a first time conversation, even if it's just kicking the tires on, like, do you need to go to search? Do you even need to hire this person? Identifying what are the business problems at hand or put otherwise, what is bubbling up in your business that is causing pain points that make you to believe that you even needed an executive.

And like starting with the what and the why is super helpful to then unlock the who so like my first question was what are the business problems you need this person to solve? And where do people that have solved these problems tend to live? often I think like if you miss that first step. Then what you end up doing is chasing names and chasing shiny objects, and that either leads the search going unfilled, or worst case scenario actually is getting someone in the door and they take the job, but then they actually don't have the skills to solve the problem that you needed them to solve in the beginning.

The first thing is why do you need this person? What's happening with, your business? And then a formulated hypothesis on who would be the right person to even solve that problem?

Jodi Jefferson: When I think about the CEOs that I've worked with. they're obviously hiring a person, but really what they're trying to do is get some sort of relief from like a constraint that they have or they want someone to unlock growth for the company. and the goal of the search process is to really remove surprises once someone is onboard.

And so the questions that I ask, um, are all obviously in service of that. with the CEOs I would say the number one question is why are we hiring for this role now? Like, what problem are we, are we solving? So really focusing on the, the why before what they will do or who to recruit.

That's like a real critical question to start with.

Keith Cowing: I love that framing from Jody. Remove surprises once someone is on board. It's a huge part of your job and it's a big part of the game to make sure that you can not only find the right person, but graft them onto the team once they join. Now, assuming you've clarified why you're hiring somebody and what you really need in the company, now, you start looking at resumes.

There's a trap that people frequently fall for. I'll let Michael describe it.

Michael Cullen: One mistake I've seen CEOs make is hire the person they think they should wanna hire versus hiring the person they need in the next 12 to 18 months. And so they get. Potentially too attracted to big names on resumes or big brands and don't really think about where they are today and what their business needs.

And so getting a little bit enamored with the person that has the background from the big, 5,000 person company without realizing that, maybe that's where they're going, but that's not really who they are today. And then that person gets in there and it's just a, it's a different.

Thing when you're running a product organization on that scale, it's much more about orchestration organization, or organizational architecture. Whereas in these startups it's, so close to sales, so commercial, so with the customer. And so it can look a lot different in terms of how they operate and what this cadences should look like.

Keith Cowing: Now in practice, when the rubber hits the road and you're comparing candidates and you're deep into a search, it's frequently not the candidate that glows on paper as the one you think you're going to be excited about. That ends up working out the best. If you're very careful about what you're looking for.

I'll let Chris give you a great example.

Chris Running: I recently ran a CPO search for a series C company there a SaaS company in the health tech space growing rapidly, and they. Had had some attrition on their team and also needed someone who could help think about how they scaled into the enterprise space from a product perspective and moved up, from SMBs to more enterprise.

So there was two business problems at hand and there was two candidates on paper, both of which had open-ended questions. So, on one hand, I'll give you two examples. One hand it looked like a killer on paper. And they were at one of the fastest growing companies SaaS companies to date. Had seen them through the perfect growth, had all the brands and logos on their resume that you would want to see.

However, they had recently stepped into more of like an IC zero to one new product initiative strategy type role. And so when we dug in there a little bit, we realized, yes, they have the brand. Yes, they've done the thing, they check all the boxes, but actually in this case, they needed a really, really strong people leader who could inspire, who could hire, who could mentor, and who could really be like a strong people leader that folks would look up to and that would inspire the team.

And so when we chatted with this person, that wasn't their spike. Their spike was like, what do I build scrappy early days and actually do the building themselves rather than the building of the team? Build the product, not the team. And so for all of those reasons, they got to almost the final stages.

And then once they really spent meaningful time with this person, they realized like we would be hiring them for the wrong reasons. They would look good on paper, but they wouldn't actually, put a stop to some of the problems that had been bubbling up. On the flip side, they had someone that looked less attractive on paper.

Okay, so this was someone that was coming from the health tech space and their hypothesis was, enterprise SaaS is better. Like SA B2B SaaS is better than health tech, and the caliber there is different. And it was a talent pool that we had decided to spend not a ton of time in. And so there was these preconceived biases going into into the conversation.

But when I was on the phone with the candidate and I was asking specific questions around, where was the team at when you joined and what happened during your time there with the team product aside. That was one of my questions. And this person told me about how they had inherited a team where the NPS score of the team was like in the low thirties.

They came in and brought that percentage point up to the high seventies in like a six month span. Turned the morale around, turned the trajectory of the team around. And I really uncovered in a quick call that like their spike was the leadership. As soon as she talked to the CEO, it became very obvious this is our person, you know, she was highly sought after in the market.

They ended up closing her and it kind of goes back to put your logos and your brands and like your preconceived notions aside and focus on what is the business problem here that needs to be solved? for her it was like she was clearly that inspiring leader that they were looking for.

And so once we asked the right questions, she was the clear winner where she was the less obvious one on paper.

Keith Cowing: There's a big difference between building the product and building the team, and you need to be really clear about which one you're looking for or if it's both. There are different moments in different companies at different times, and your needs will determine who the right fit is. And so if we can't rely on the resume and the flashy names, the flashy logos, how do you find the right person?

Michael has an excellent technique that might change how you look for your next candidate.

Michael Cullen: One thing I like to do is look at the person before the person. So finding the person that was, you know, at a, maybe a rival startup or a similar business that's 18 months ahead of them and say, okay, where was their CPO before they were there? 'cause if you start to dial the clock back, we're, we're trying to find someone that's on an upward slant.

We're not trying to find the person that's, already at cruising altitude, that person's gonna be more expensive. They may have come up in a different kind of product environment that we're in right now. And so a lot of it is trying to find, you know, the executive before they're the executive. And then looking at other businesses, looking at other competitors, similar businesses in saying where was that person six months before they hired them?

And how do we go find someone that looks like that?

Keith Cowing: So we're looking for trajectory, not altitude, which is an important distinction to think about. And now as we progress through this search phase, the next thing is to assess the candidates that are in front of us. Jodi has a great breakdown for this to think about how to evaluate whether or not these people have what you're looking for.

Jodi Jefferson: Every search is so unique, even when the title is the same and you would think, okay, it's, you know, I have a bunch of series B product hires, VP product, same title. It's, it's always different, each one. And so I really try to evaluate what. Transferable product experience they have, but also their, their judgment and, and how I think they'll mesh well with the team, not just titles.

and so I think for series A through C specifically, that that stage I do think about a couple of things. I break this down in a few areas, so I wanna understand whether their, instincts as a product leader were shaped. How they were shaped inside the environments they're coming from, and were there comparable customers and workflows and constraints.

And the constraint thing is big in this stage. So the key question is like, has this person built. Products in similar product constraints, how relevant does that experience? So a few areas that, I'll break that down is the stage, the speed is a critical advantage at Series A through C.

It's what might make or break the company. And so, the questions and the things that I really focus on are like, have they made trade offs? Uh, how have they made trade offs to, you know, ship quickly and, you know, how comfortable are they operating? And ambiguity and how have they placed, um, bets under uncertainty or under time pressure.

So I think that's really, really critical. And then also, um, zero to one versus the scalers, you know? So are these greenfield builders great at pre-product market fit and rapid experimentation, or are these the people that are coming from maybe a little bit more mature organizations where.

They know how to place the bets and they know how to move fast, but they're also introducing structure in a really thoughtful way without slowing things down.

Keith Cowing: Now after you've found somebody with the right skills and the right judgment, we also have to assess culture fit. How do you assess culture fit? Michael does something, many recruiters don't, and he thinks it's non-negotiable.

Michael Cullen: I think one of the most important things you can do as an executive search professional is to walk the floor. Of the client and just go into the office, just get a feel for the place. Understand, do they eat lunch together? Do they eat lunch at their desk, are they smiling all the time and really laughing.

Is it more of a kind of computer driven you know, slack driven culture? Like where, what does this company feel like, and then how do you kind of transpose this person in there? Because I think if you're operating in this like zoom, from behind a screen and not really understanding the true kind of human elements of the company, that's where you can really get things wrong from a executive search for perspective.

'cause you see the great profile, they've got the great experience, but you can get a situation where it's oil and water if the sort of vibes are off.

Keith Cowing: Picture's worth a thousand words, like a walkthrough is worth a million words. It's just, there's so many little observations you can be making just in terms of how other people are interacting, how the business culture comes to life in the office.

Michael Cullen: And it's not to say that one is better than the other. It's not to say that the more introverted, slack driven culture isn't. Is worse than the more rowdy, smiley kind of sales driven culture. They're just different and they both can be successful. But certain people are gonna do better in, in one versus the other.

And so if you don't have that feel and you don't think about who is this person? What is this candidate? Like, how do they communicate? What types of environments have they done well in then you're missing a huge part of the equation.

Keith Cowing: And before the next part, I wanna flag this one particular quote from Michael because he has a question where a lot of people reflexively give the same answer and he hears it frequently, and it's probably common and he thinks it's a complete red flag. So pay attention to this one.

Michael Cullen: A question that I, I often ask, and this is this way, the future candidates is like asking people about management, uh, and asking people about how they manage and, and seeing if they. To quickly go to, like, I'm not a micromanager, I don't get into the details. I like to give people a lot of slack.

I like to give people a lot of room for whatever reason. That seems to be like the du jour answer and I generally find that that's a terrible answer to that question. I think great management is in the details is as close to the cutting room floor as they need to be, especially in sort of the current environment where so much of this sort of senior to IC work is getting collapsed with AI tools and, and just trimmer, organizational structures. And so I actually look for folks that wanna be more in the details that aren't embarrassed to say that they really care about sort of these small things and making sure that they go right because I just, I think it's sort of like the way you do any, you know, the way you do a anything is the way you do everything.

And so if you're not in those details and you're not paying attention. You know, I think that's gonna bubble up to much bigger problems within an org.

Keith Cowing: That's why the head of product job is so hard and so important. You have to do the strategy and the details at the same time. It's not either or. Build the product, build the team and everything in between. Now, let's address the elephant in the room, which is ai. How do you look for people that understand ai, know how to use AI and know how to apply it in an organizational context?

I thought Jodi had a very balanced and nice answer to think about.

Jodi Jefferson: The best product leaders today aren't just adding AI features or tools. They're really. Believing that AI fundamentally changes how work is getting done and, and they recognize that this is a huge organizational unlock.

So they might not have already like deployed it in production and have products in the market that they can report back on the ROI. If they do great, but if not, it's just that understanding. How work gets done and how teams can be more efficient and, and have actually implemented that. , Speed and leverage is an advantage. So with ai you have a huge unlock for this. Right. You know, so I, I'm trying to, you know, connect their experience with what. Uh, to meet the company where they are again, like some people are way ahead of the game.

Some people are, some companies are not. So I, I just, I try to value the leaders and get the stories of, uh, how they're connecting AI directly to business performance. How they're connecting it directly to product and customer experience to unit economics. Have they, have, they deployed it into production and.

What are the measurable outcomes that they've seen? Again, some people have that, some people don't. This is changing rapidly. Uh, and then just if they're coming out of environments that are AI native, which is a term that we hear a lot, is it just, is AI central to the products value, the value proposition?

Like that's for me, you know, at, its at its core what I'm trying to uncover. And then just, yeah, how they've, how they've evolved workflows using ai.

Keith Cowing: There's this underlying tone about how AI is not just changing our products, but our organizations and how we work and everything about how we approach business. Dennis Crowley had a really interesting and honest perspective on what it means to behave differently as a product team, and as somebody who's been a product leader and a product driven CEO, his whole career, he still hired somebody to do this role earlier than ever before because he thought it was so important to have somebody that's AI native.

Dennis Crowley: I've always thought that I was more of the product type of c of CEO. So I can be like, all right, I can fill in for the head of product for most things. And I did that for a long time at Foursquare before we eventually hired. People to run it. With the project that we're working on now, just because like the tools are so different, uh, we hired a lead product person almost immediately just because I met this woman who was a.

Just like very, very skilled, like really into the product and had worked in stuff in adjacent spaces and was very fluent in like, AI tools and technology. And it's like, you just know not only do you know stuff that I don't, but you know how to work in a way that I don't know how to work. You know, given that, like, I think there's. A whole crop of of, younger folks that are just, AI tools first, where I feel like I have to work to kind of make the AI tools native to my workflow. It's like just, organic for some of these folks. Um, so that was, that's different.

And it's been wonderful because I feel like from the beginning I kind of have like a, a counterpart to, to bounce ideas off of.

Keith Cowing: Okay, so we've made a lot of progress. We identified what we need. We brought in the right candidates, we assessed them, we interviewed them. Now you get make a final call and you have to have conviction. And so what does it mean to have conviction and how do you get there as a CEO

Chris Running: I'll give you an example that came up recently. I was working with the CEO and they wanted to hire someone. It's the top job. For a really scaled company. Product and engineering combined is probably a 200 person organization.

And the person that was like the killer, the person who had, the. Outperformed every other candidate was more of an underdog. Like they were, they had less experience and they had a VP title. And so the hiring the hiring manager kept alluding to like, oh, but not the top job. Not the top job.

And so I had to say, Hey, you're meeting this person. And you know, and they actually met up at a conference recently. You're meeting them face to face. And this is probably your last conversation. If you don't have conviction, your board's not gonna have conviction. And if you don't have conviction at this point, it's gonna be really hard to close them because they also are gonna be like, they have a lot of, they have a great thing going too.

And so if you don't have conviction, even before we get to the close, it's not gonna work. So I said, spend your time. Ask them. ' in this instance, , there had been technical founders. Who had left and this person had stepped into the number one job but just didn't have the C title.

And I knew that. But it's kind of one of those questions that doesn't always make its way into the assessment process. Like the interview questions, it's kind of a weird thing. So I, coached the hiring manager. I said, Hey, I want you to ask them, Hey, when the co-founder left the, you know, the CTO co-founder who was previously overseeing product and engineering when they left.

When was that? How did your remit change? How did your scope change? What were the things that felt really different for you? And it was so funny, he showed up to the meeting. It was like the same day that he had met with that candidate, and he was like, you were both right. It was me and one of the investors on the call.

Keith Cowing: He was like, you were both right. Definitely in the top job. Reports into the board has like absolute responsibility of like the C title. In fact, I'm actually nervous now. I'm like, can we close them? What's gonna happen when we give 'em the offer? They're sure gonna get countered with the C title. Okay. Now let's flip the tables for a second. What advice does Chris have for candidates assessing the CEO and the opportunity?

Chris Running: And then on the candidate side, I think sometimes if you have open-ended questions on like the product itself and the caliber of the product or the caliber of the team, that can also be like a really. Tricky thing to ask a CEO or a hiring manager about without offending them. Basically like, what's the caliber of your team?

Is your product really what you say it is? And like, how do I pressure test this in a way where I feel confident and I don't come in and realize it's something I didn't sign up for? And so in the case of this one, what I told the candidate was, I said like. There's a few things you can do on your own.

Of course you can go on LinkedIn and you can look at the people who are there and who were there and get a sense of quality and tenure. But I actually don't think that matters. Um, I actually don't even think it matters who's on the team today. What matters is do you have full ownership and autonomy to build the team that you have the conviction that you need to build in order to build the product That is gonna be a winning product.

And so what I encourage the candidates. I actually wouldn't spend your time on who's on the team and should I meet them. I would spend your time on what responsibility and autonomy will I have in shaping the direction of the team, the location of the team, the strategy of the team, strategic hires, the budget for that team.

And if you have like full autonomy and trust from the leader, then like the rest doesn't really matter. And so that was the conversation that they had as well.

Keith Cowing: I work with a lot of CEOs and CPOs and VPs of product, and that relationship fails at least half of the time, and a lot of that is avoidable. Now let's listen to Jody, 'cause she calls out one of the main failure modes that you get into when this situation doesn't work. And as a head of product or as a CEO, you wanna avoid it at all cost.

Jodi Jefferson: In many cases, sometimes when there's like a, a hiring, you know, failure, it's, it doesn't come from that person not being qualified. It's just like misaligned expectations. companies and candidates not asking the right questions upfront. And so the role of the search process is to surface those realities and allow everyone enough time.

You know, I think companies are usually spending at least a minimum of 10 hours, if not more, with a candidate at the executive level before a hiring decision is made. And there's also, um, there's, you know, board meetings, there's working sessions, there's multiple touch points , with the CEO. The CEO may have had board pressure to make this higher, you know, but at this point, they really should have the clarity in terms of why they're making this hire.

And are we targeting the right level of talent? You know, sometimes that's, the leveling is always really interesting with these searches.

you know, I think the hardest part sometimes for me and my job is not finding the right talent. It's just like calibrating level. And so I think CEOs at this stage. I think what they wanna, what they're, what they're kind of, I guess what their fear might be is like, can this person operate at startup speed?

Would they want someone with vision, but are they actually too strategic and not operational enough? Will they slow us down? So like, these are some of the, the sort of fears that might be surfacing that I encourage them to really discuss and obviously throughout the process surface.

And then for the candidates, I think. They might be thinking does the CEO really want a, product partner and a, and a, product visionary? Or do they just want someone to execute? Like, will I truly own product decisions? And so I think these are just sort of like some of the elephants in the room that should be addressed during the process, like decision ownership.

Leadership expectations, success definitions, like 12 month review. Let's envision what this looks like. What I always say, like, if this candidate knocks it out of the park in 12 months, what will they have accomplished? And if a CEO can't answer that upfront, we shouldn't be making the hire yet because we might make the wrong hire.

How will we know if they're successful? So defining outcomes is really important upfront.

Keith Cowing: Don't forget, you need to be crystal clear about what knocking it out of the park looks like in 12 months. Now let's transition to selling. How do you actually close the best candidate and get them on board?

Michael Cullen: I think for the most part you should be able to get the compensation things lined up if you're the right person in the right place. I think what they're really worried about is like making the wrong decision and. Committing their life and their career into this new thing.

That's, I think, a lot more challenging than the financial piece of it. I think a lot of really successful execs, have have done well in their career, have, plenty of opportunities. So it's really more about investing their time and their sort of career chips on this thing. I think the best way to do that is to, one, really get to know the candidate and what they, what makes them tick.

Understanding them as deeply as you possibly can. Understanding how they, what does their spouse think about this? Are their kids gonna have to change? Schools are they gonna be able to make it home for dinner? All those little things are really critical when you think about moving someone from one job to another.

And then also. Can you get validation that is not just you, the recruiter or the CEO in this role? So can you bring in an investor who's obviously a little bit biased, but maybe just brings a third party point of view? Can you bring in a touchpoint of someone they know that knows the CEO so that they can feel comfortable in that back channel?

But I think it's all about getting the candidate really comfortable with making this big jump and it's again, less, obviously the compensation is critical and you can't ignore that. But most of the time when these things go south, it is because something broke in the trust building exercise.

Not because they were off by,, X dollars.

We're not recruiting a, a new BFF for the CEO. Uh, so it's not about are you guys gonna be best friends when you guys hang out?

And, uh, you have all the same interests and you watch the same TV shows, but if you can get them into that sort of human to human realm and sort of break, break out of this negotiation I think that's really powerful in getting candidates across the finish line.

Keith Cowing: Now Chris closes us out on something all CEOs need to hear about what's happening in the market right now.

Chris Running: Especially on closing, by the way, and I think that we're in this, we're in this moment of time where the market is transitioning from an employer's market where, call it the last two years, there wasn't as many opportunities at the C level. There wasn't as much money flowing. To an employee's market where the best candidates are spoiled for choice again, and I think that founders and CEOs need to be like ready to compete for the best.

And so I see this awkward thing happening where they're, they've, you know, the hiring managers have kind of been spoiled over the last two years. Now. Candidates are spoiled for choice. And so there's this interesting shift that we have to make from, hey, like you really do have to have conviction in why your job and your company is the best and it's prepared to win, and like you're gonna miss all the swings you don't take.

So like, let's get ready to really compete for this top talent. And I don't think that hiring managers have had to compete at the level that we were back in, I don't know, five, 10 years ago.

Keith Cowing: What an amazing episode full with great information from our guests. Let me leave you with my five key takeaways. Number one, start with why. Be super clear about what knocking it outta the park in 12 months looks like. Number two, avoid the logo trap. People might have the flashy logos and the perfect resume.

It does not mean that they have what it takes to lead at a series A, to series C startup. Number three, evaluate exactly what you need for the next 12 to 18 months and be crystal clear about that. Number four, check for the human stuff, the culture fit. Walk the floor, see if they're going to gel with the team.

And number five, close with conviction. You have to have conviction because if you don't, they will feel it. Go compete like you mean it. And a huge thanks to Chris Running , Jodi Jefferson, Michael Cullen, and Dennis Crowley for being wildly generous with their time and their insights,

if you're a head of product or a CEO o, you can find me at KC Do Coach, and you can find our wonderful recruiters at the links in the show notes. This has been another episode of Executives Unplugged. I'm Keith Cowing. Until next time, enjoy the ride. Okay.