The Truth About Hiring Your First Head of Product

**Dennis Crowley** (0:00)
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 the tools are so different, we hired a lead product person almost immediately, just because I met this woman who was very, very skilled, really into the product, and had worked in stuff in adjacent spaces, and was very fluent in 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** (0:38)
This is Executives Unplugged. I'm Keith Cowling, 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. Focus 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 belt out their executive teams, and Dennis Crowley to get that CEO perspective. Let's jump in. 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 to clarify? I think this one's really important because as a coach, I find a lot of founders and CEOs skip this important step, and it's one of the most critical things to determine whether or not the hire works.

**Chris Running** (1:36)
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? Is 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 to 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** (2:30)
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. They're in the goal of the search process is to really remove surprises once someone is on board. And so the questions that I ask 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 solving? So really focusing on the why before what they will do or who to recruit. That's like a real critical question to start with.

**Keith Cowing** (3:10)
I love that framing from Jodi, 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** (3:34)
One mistake I've seen CEOs make is hire the person they think they should want to hire versus hiring the person they need in the next 12 to 18 months. 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. 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. Then that person gets in there and 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 cadence should look like.