The Truth About Hiring Your First Head of Product

Three top executive recruiters and Foursquare founder Dennis Crowley reveal why the candidate with the perfect resume is usually the wrong hire — and how to find the right one.

Most CEO-CPO relationships fail within the first 18 months and a lot of that pain starts with how the hire was made in the first place.

In this episode, I sat down with three of the best executive recruiters in the business — Chris Running, Jodi Jefferson, and Michael Cullen — plus Dennis Crowley, founder of Foursquare and Hopscotch Labs, to unpack the biggest mistakes founders and CEOs make when hiring their first VP of Product or CPO at Series A through Series C companies.

We cover: why many searches derail, the logo trap that seduces hiring managers into picking the wrong candidate, why you should look for trajectory over altitude, the management answer that's a complete red flag, how AI fluency is reshaping what "great" looks like in a product leader, and what it actually takes to close top talent in a market that's shifting fast.

Whether you're a founder about to make this hire or a product leader evaluating your next opportunity, this episode gives you the playbook from both sides of the table.

Chapters

01:13 Start With Why

03:10 Avoid Logo Trap

04:28 Real Search Example

07:50 Trajectory Not Altitude

08:48 Assess Judgment & Speed

10:52 Culture Fit Walkthrough

12:28 Management In Details

13:59 AI Native Leaders

17:15 Hiring With Conviction

19:23 Candidate Due Diligence

20:48 Align Expectations

23:19 Close The Candidate

25:13 The Market Shift

26:14 Five Takeaways

Find the guests on LinkedIn:

Jodi Jefferson: https://www.linkedin.com/in/jodijefferson/

Michael Cullen: https://www.linkedin.com/in/cullenmm/

Chris Running: https://www.linkedin.com/in/chris-running-a94a8025/

Dennis Crowley: https://www.linkedin.com/in/dpstyles/