Hilary Gridley

Head of Core Product at Whoop

Head of core product at Whoop, previously senior director of product at Big Health and senior product marketing manager at Dropbox, known for helping product teams learn to take on hard problems, deal with setbacks, and thrive through uncertainty.

The Org Builder The Craftsperson

Dimension Profile

Strategic Vision 45%

Execution & Craft 55%

Data & Experimentation 30%

Growth & Distribution 25%

Team & Leadership 90%

User Empathy & Research 55%

Key Themes

learning to take a punch as a product leader managing fear and uncertainty in teams AI-era product leadership adaptation counter-programming negative narratives through action embracing hard product problems controlled voices in your head as a leader

Episode Summary

Hilary Gridley shares her philosophy of helping product teams learn to take a punch and thrive through uncertainty, particularly relevant as AI transforms the nature of product work. She explains why the voices in your head will eat you alive if you don't control them, how to counter-program negative narratives through action rather than litigation, and why more people should embrace hard problems that are likely to fail but are worth doing. The conversation is packed with practical leadership advice for managing fear, building resilience, and leading teams through existential uncertainty.

Leadership Principles

→ Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive
→ When someone is upset about how they're perceived, focus less on litigating another person's impression and more on what action to take to demonstrate who you really are
→ In the story of work, you are probably not the protagonist — people think the game is about influencing the CEO, but you're not special

Notable Quotes

"Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive."
— On the psychological challenge of product leadership

"I would really love it if more people were like, 'Screw it. I'm going to do something that's probably going to fail. It's important and it's worth doing and I'm going to do it well.'"
— On encouraging teams to take on hard problems despite fear of failure

"People think that the game is all about influencing the CEO, influencing the people around them. You come up thinking like you're the protagonist. But in the story of work, you are probably not the protagonist. You're not special."
— On the humility required for effective product leadership

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