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This CPO regrets that product management exists | Tom Verrilli (CPO of 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: 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.

Tom VerrilliguestLenny Rachitskyhost
Aug 2, 20261h 24mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Rethinking product management: fewer PMs, more IC work, AI leverage

  1. Whatnot uses “we regret product management exists” as a forcing function to only hire PMs when there’s a clear, specific need rather than defaulting to PM-per-team ratios.
  2. Over-specializing PM work can “infantilize” engineers and designers by removing decision-making reps, while the best orgs keep product judgment close to builders and customers.
  3. Whatnot runs a lean PM org (~20+) and assigns PMs to high-priority problems every planning cycle, not permanently to engineering teams, to maximize leverage and learning.
  4. Hiring signals are shifting away from “alignment/stakeholder politics” toward systems thinking, fast validation instincts, and concrete evidence of building/iterating real products.
  5. AI is increasing IC leverage (especially in data work and codebase understanding), pushing orgs toward senior ICs doing hands-on work and changing which roles and skills compound over time.

IDEAS WORTH REMEMBERING

5 ideas

Don’t staff PMs by ratio; staff PMs by necessity.

Verrilli argues the default “pod ratio” (e.g., 6 engineers = 1 PM) creates PM bloat and reduces builder ownership; instead, add PMs only where the work truly needs a specialist to drive decisions and clarity.

Over-abstracting PM work weakens engineering/design judgment.

PMs can become “babysitters” if they absorb all customer context and decision-making; keeping engineers/designers closer to those reps builds stronger product instincts and faster local decision-making.

Map PMs to problems, not to teams, to follow the highest-leverage work.

At Whatnot, PMs are reassigned regularly based on six-month priorities and DRIs, which prevents role stagnation and ensures PM time is spent on the company’s most important outcomes.

The hiring bar is shifting from politics to craft.

Whatnot screens against candidates who lead with “alignment” and stakeholder narratives, favoring those who can show macro+micro thinking, rapid validation plans, and specific examples of decisive building in ambiguous environments.

Systems thinking is a learnable muscle—practice outcome-contingent planning.

A simple training loop is asking “What do we do if it’s green? What do we do if it’s red?” plus mentally simulating scale and second-order effects before writing docs or code, then moving anyway (“know then go”).

WORDS WORTH SAVING

5 quotes

Hiring so many PMs infantilizes the engineers and the designers who are perfectly capable of making good decisions, but just never had to because there was always a PM to babysit them.

Tom Verrilli

We articulate it that way to force ourselves to remember that you don't hire a PM just for the sake of hiring one. You hire one where there's really specific need.

Tom Verrilli

There's definitely a group of PMs whose specialty wasn't technical, it was politics.

Tom Verrilli

We took all of our A players and then promoted them out of doing things. Why wouldn't you want Messi playing for your team rather than trying to have the academy coming along all the time?

Tom Verrilli

Sometimes things aren't actually that complicated. It's just weak leadership.

Tom Verrilli

“We regret product management exists” philosophyPM specialization vs. builder decision-making repsWhatnot PM org design (buyer/seller/trust & risk)Assigning PMs to problems vs. teamsHiring: product theater vs. real craftSystems thinking and risk pre-mortems (“know then go”)Senior IC resurgence; fewer layers and faster decisionsAI leverage: data, codebase comprehension, regression detectionData scientist role shift and data quality foundationsFuture product team shape and cross-functional “free space”Founder–CPO dynamics and top-down decision-making“Play the accordion” (zoom out/zoom in execution loop)

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