As a company scales, there's a temptation to hire for big-name credentials. Instead, Hims' CEO prioritizes candidates who have demonstrated grit and resilience through chaotic, high-pressure situations, valuing these "builders" over polished, non-startup "strategists."

To be truly successful, a product leader cannot just focus on features and users. They must operate as the head of their product's business, with a deep understanding of P&Ls, revenue drivers, and capital allocation. Without this business acumen, they risk fundamentally undercutting their product's potential impact and success.

Prioritize candidates who have navigated difficult situations. They learn more from tough times than from being at a constantly successful company where mistakes might be masked by overall growth. Adversity builds crucial problem-solving skills and resilience that are invaluable to a growing organization.

When evaluating senior candidates, don't view a failed entrepreneurial venture as a negative. It often indicates valuable traits like risk-tolerance, scrappiness, and resilience. These leaders have learned hard lessons on someone else's dime, making them potentially more effective in a new organization.

Organizations often appoint leaders from operations, law, or marketing to run product. These leaders lack fundamental product management experience, leading to weak strategy. Unlike in sales, where failure is quickly visible in revenue metrics, the damage from poor product leadership only surfaces years later, allowing ineffective leaders to remain in place.

Actively recruiting entrepreneurs whose own ventures recently failed brings in smart, driven individuals with high ownership and a hunger to prove themselves. This is invaluable in the early, capital-constrained days when you need a team with a founder's DNA.

Great product managers are defined by inherent qualities that are difficult to teach. Focus hiring on proactivity (a bias for action), curiosity (a desire to learn and challenge assumptions), and resilience (the ability to bounce back from failure). These traits, more than domain knowledge, separate good PMs from great ones.

Beyond IQ and EQ, interview for 'Resilience Quotient' (RQ)—the ability to persevere through setbacks. A key tactic is to ask candidates about their proudest achievement, then follow up with, 'What would you do differently?' to see how they navigated strife and learned from it.

To successfully bring modern tech to an industry stuck in the past, a product leader needs more than just technical skill. They require deep empathy to understand the user's current challenges and the tenacity to keep iterating until the new solution feels like a natural and empowering evolution for them.