EPISODE · Apr 7, 2026 · 27 MIN
The Truth About Hiring Your First Head of Product
from Executives Unplugged · host Keith Cowing
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.Chapters01:13 Start With Why03:10 Avoid Logo Trap04:28 Real Search Example07:50 Trajectory Not Altitude08:48 Assess Judgment & Speed10:52 Culture Fit Walkthrough12:28 Management In Details13:59 AI Native Leaders17:15 Hiring With Conviction19:23 Candidate Due Diligence20:48 Align Expectations23:19 Close The Candidate25:13 The Market Shift26:14 Five TakeawaysFind 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/
What this episode covers
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.Chapters01:13 Start With Why03:10 Avoid Logo Trap04:28 Real Search Example07:50 Trajectory Not Altitude08:48 Assess Judgment & Speed10:52 Culture Fit Walkthrough12:28 Management In Details13:59 AI Native Leaders17:15 Hiring With Conviction19:23 Candidate Due Diligence20:48 Align Expectations23:19 Close The Candidate25:13 The Market Shift26:14 Five TakeawaysFind 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/
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The Truth About Hiring Your First Head of Product
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