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Hilary Gridley

Hilary Gridley

20.7K 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

Hilary's course is very well structured, contains lots of great tips and tricks to integrate AI in the workplace in a thoughtful way. The classes are hands-on, with lots of opportunities to practice building AI tools and to ask questions. The lifetime access to resources is also extremely valuable as we all continue in our AI learning journey.

Noella

May 2026
Manager, Operations - Content Enablement (Bilingual) · Acuity Insights
Hilary has a great combination of subject matter expertise and passion. The course is extremely hands-on (learn by doing), and I was impressed with the amount of effort she put into the live courses as well as supporting the participants with extra information and time on an as-needed basis.
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Nate

May 2026
Sr. Director, Product
Hilary's course was fantastic. The content was exactly as advertised, but what I really enjoyed was the interactive course structure that she custom built on her website to facilitate learning. The exercises were practical and rooted in enhancing our individual leadership strengths using AI.
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Khet

May 2026
head of product · MarkerHeads
Hilary and her team were exceptional teachers on all things AI. With the current evolving landscape, she did a wonderful job keeping us up to date on the latest and greatest in terms of approaches and tools. Double thumbs up for the very specific lens towards people managers in this course.
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Catrina

May 2026
Sales Manager · Lattice
If you're expecting a course about AI tools and tech stacks, this isn't it. From the first session, Hillary asks you to look at your own work before reaching for any tool. The framework is deceptively simple: clarity and ownership. Be clear on the why and the what before you delegate, and stay the author of whatever comes back. Hillary makes you learn this through real problems that push you past the first answer that feels good enough. That's where the course lives. Anyone who wants to work with AI seriously needs these foundations first. I left knowing how I want to work with AI.
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Nanda

May 2026
Chief Product Officer · Besso.com