Whatnot

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 Mercury—Radically different banking, now with Command — 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 • Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling • E-fish.com: https://www.e-fish.com — 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. To hear more, visit www.lennysnewsletter.com

Tom Verrilli

Chief Product Officer

Whatnot

Grant LaFontaine is the Founder & CEO @ Whatnot, the fastest-growing marketplace in the US, empowering people to make a living off their passion. To date, Grant has raised over $225M for Whatnot from the likes of CapitalG, a16z, YC, Scribble Ventures and Wonder Ventures to name a few. Prior to Whatnot, Grant was a PM @ Facebook working on the Oculus App Store and before that was the founder of Kit.com, ultimately acquired by Patreon. In Today's Episode with Grant LaFontaine You Will Learn: 1.) The Founding of Whatnot: How did Grant make his way into the world of tech and startups? What were some of his biggest lessons from Facebook? How did that impact how he has built Whatnot? 2.) Impossible To Hire Product Managers: Why does Grant believe it is impossible to hire product managers today? How does this impact the decision-making powers of engineers? How does Grant test for this product knowledge in all engineers he adds to the team? What are clear signals of 10x engineers in hiring processes? 3.) A/B Testing and Risk Mindset: Why does Grant not believe in the effectiveness of A/B testing? Why does it not work? Why does Grant believe one of the biggest reasons for startups failing is they do not take enough risk? How does Grant try to ensure that his team takes as much risk as possible with everything that they do? How does mindset to risk change with scale of company and with leadership? 4.) AMA: Why does Grant disagree with founders angel investing? What are the biggest challenges Whatnot has faced in scaling? CEO coach? Who? When? What is the biggest lesson? What is the single driving metric of Whatnot? How does Grant advise founders to determine their North Star metric? Item's Mentioned In Today's Episode with Grant LaFontaine Grant's Favourite Book: Foundation: 1/3 (Foundation Trilogy)

Grant LaFontaine

Founder and CEO

Whatnot