Hilary Gridley
Head of core product at Whoop (at time of recording). Previously senior director of product at Big Health (digital therapeutics — clinically validated mobile apps for insomnia, depression, anxiety; built a depression therapeutic before a competing product was acquired) and senior product marketing manager at Dropbox. English major.
Author of “How to Become a Super Manager with AI,” the sixth most-read post in Lenny’s Newsletter. Teaches a Maven course on the same topic. Newsletter: hils.substack.com. Cross-over guest between Lenny’s Podcast and How I AI with Claire Vo.
Known for: the “take a punch” framework (counter-program the narrative rather than litigating impressions); transparency as teaching how leaders think, not just what they decided; habit formation for AI adoption (consistency, friction reduction, reward loop design); “magic questions” technique (statement + “do you agree?”); the behavioural activation principle (act first, feel better second, drawn from CBT); and the not-the-protagonist insight about reporting to a CEO.