LearningProductCareersSkillsEducation Whoop’s head of product asks why learning a job has to take two years, and her drills are the closest thing to an answer

Hannah Lindqvist

10 min read5 hours ago

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In June 2025, Lenny’s Podcast published its episode with Hilary Gridley, head of core product at Whoop, previously at Big Health, where she built clinically validated digital therapeutics, and before that at Dropbox. Most of the conversation was about management, and I will leave that part alone. The section I keep returning to is about learning, and it turns on two tools she built and one question she asked. The first tool is a custom GPT she prompted to “Create LSAT style questions to test logical reasoning, but put them in the scenarios of things that a PM would encounter.” The second is a t-shirt-sizing GPT that lets a product manager practice engineering estimates many times in an afternoon, where the real job offers that practice about twice a week.…