Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history). *In our in-depth conversation, we discuss:* 1. Why Whatnot’s product team was founded on the premise “we regret that product management exists” 2. How AI is reshaping the PM role 3. What Tom looks for when hiring PMs 4. The shift toward senior ICs doing the work 5. How AI has transformed data science at Whatnot 6. Tom’s “play the accordion” mental model 7. Why “hire great people and get out of their way” fails 8. His biggest lessons from his time at Twitter *Brought to you by:* WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/ *Episode transcript:* https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Tom Verrilli:* • X: https://x.com/tdrobbo • LinkedIn: https://www.linkedin.com/in/tom-robertson-042 *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction (02:40) “We regret that product management exists”: what it means and why (08:30) When specialization makes sense, and when it doesn’t (15:20) How Whatnot structures its PM org (17:28) What 31,832 PM applications revealed about the function (19:40) How to develop systems thinking (22:10) The shift to senior ICs doing IC work (32:26) Advice for PMs struggling in today’s market (35:22) How AI has transformed work at Whatnot (41:14) The data scientist problem (42:48) Which roles are trending up and down (44:48) What the product team of the future looks like (46:29) Why core PM skills are the most durable in an AI world (49:23) How to get the most out of the people you hire (53:32) Navigating the CPO-founder relationship (57:34) Advice for aspiring CPO’s (59:16) How to know when to stand firm and when to step back (01:01:38) Play the accordion: balancing strategic vision with fast iteration (01:06:35) Agentic commerce vs. live commerce (01:09:46) Lessons from Twitter (01:13:07) Failure corner (01:15:45) Lightning round and final thoughts *Referenced:* • Whatnot: https://www.whatnot.com • Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc • Twitch: https://www.twitch.tv • Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future • Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus • Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th • Hex Threads: https://hex.tech/product/threads • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine • Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head • Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear • Kara Swisher on X: https://x.com/karaswisher • Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY • Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1 • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app *Recommended books:* • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205 • The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063 • Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439 _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.