

Live AMA with Hilary Gridley, Head of Core Product & AI of WHOOP
Join us live with Hilary Gridley, former Head of Product and AI at WHOOP, where she led the teams behind the core WHOOP experience and the company’s AI powered coaching platform. Hilary built her career at the intersection of behavior change, digital health, and product innovation, previously helping scale FDA cleared mental health products designed to treat anxiety and insomnia.
Her work has consistently sat at a powerful tension point: how do you design systems that help people perform at a high level without burning them out? At WHOOP, that meant turning data into insight, and insight into daily habits that actually stuck.
This is an open AMA. No heavy agenda. Just your questions.
You can ask her… anything, but definitely about:
- Building AI tools that feel human, not robotic
- Turning empathy into clear systems that drive accountability
- Designing manager habits that scale performance across teams
- Creating feedback loops that reinforce energy, resilience, and growth
- Leading product teams in high velocity environments
- What she learned the hard way building at the edge of AI and health
If you’re wrestling with how to balance care and candor, how to operationalize culture, or how to make performance sustainable instead of extractive, this one’s for you.
Bring the real questions you’re navigating right now.
Hosted by Martin Hauck from The People People Group