Hilary Gridley

Hilary Gridley

20.2K 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

Shadi

Live cohort
The biggest shift for me was moving from “How can AI help me do more?” to “What work should I actually be doing, what should my team be getting better at, and where can AI fundamentally change how the work gets done?” I also appreciated that the course doesn’t treat automation as the end goal. There’s a real focus on judgment, coaching, developing your team, and being deliberate about where humans stay in the loop. I’ve already taken several of the concepts and turned them into real workflows and skills for my team. More importantly, it has changed how I look at the work itself. Highly recommend it for leaders who are already using AI and want to move beyond prompting into actually redesigning how they and their teams operate.

Monica

Live cohort
Manager, Learning + Leadership · lululemon

Self-Paced: How to Become a Supermanager with AI

Hilary's interactive course provided an incredible experience to make agent-building more accessible. Her course is rooted in strong leadership and the ability to communicate standards and expectations - building strong agents is a leadership practice. I am leaving the course with new tools and practices.

Laura

Live cohort
Found this class very helpful, with real life practical examples that can be applied every day.

Will

Live cohort
Associate Partner · RAMSA

Build your Household OS

I recommend this course very highly. Hilary and Audrey are expert teachers, and the lessons apply far beyond the subject matter of the workshop itself.

Sara

Live cohort
Writer/ Facilitator/ Strategist/ Coach · Solo consultant

Build your Household OS

Well planned out. Excellent website with supporting materials, good to navigate. It was my first introduction to Claude Code and I felt like it demystified processes using a very real world scenario. It was validating to start emptying my head of all the tasks I'm managing and helpful to listen to others talk about how they use ai. A million times more useful than watching a random webinar. I went from never using Claude Code to having it add to cart items for my weekly shop.