Hilary Gridley

Hilary Gridley

20.4K Subscribers

Product Leader (Whoop, Dropbox, Big Health)

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Hilary Gridley will turn you into an AI-native leader

Most conversations about AI at work are about productivity. I'm interested in something harder: using AI to raise the quality bar, not just the output volume.

I teach managers how to scale the parts of their job that matter most: coaching their team, holding a standard, and turning their judgment into leverage. In my course, you'll build custom tools that systematically expand your team's capabilities.

Everything I teach comes out of 15+ years of building consumer products and managing the teams behind them, most recently as Head of Core Product & AI at WHOOP, where I led the team responsible for the core member experience and AI coaching platform. Before that, I led Product & Design at Big Health, where I built FDA-cleared digital therapeutics. Earlier stops: Dropbox, Nike, DoSomething.org.

Managers enrolled from
Google
Microsoft
J.P. Morgan
NBCUniversal
Visa Inc.

Alumni reviews

This course has been even more transforming to my work and my use of AI than I would have thought - and I had very high expectations to begin with. Highly recommended!

Johannes

May 2026
Americas Health Lead · IFRC
Hilary is a rockstar in the product building world. I've been following her since her Lenny debut and read her Substack religiously This class did not disappoint. Not only does she bring in the human element of productivity, leadership, and management, but she helps you apply theoretically and tangibly in AI contexts. This was the on ramp I needed to get started using AI in my daily work. I walked away with a clear place to start, skills I now use, and workflows that are helping me keep up and hold my team accountable. This is worth the time and investment.

Kristin

May 2026
VP Product · Learning Commons/Chan Zuckerberg Initiative
Learnt so many practical applications of AI, way beyond just being a manager. I keep coming back to the resources and recordings as there is more to take away from the course even now that is over. Highly recommend!
Reviewer profile image

Edyta

May 2026
Associate Director Technical Product Manager · AbbVie
AI Tool translation was helpful in navigating the various AI interfaces

Lesley

May 2026
Technical Product Owner · LCa
Such clear thinking and actionable guidance on how to build with AI.

Joe

May 2026
National Sr. Director, Social Media · American Heart Association