OpinionDiscussion

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | GrowthAugust 2, 20261h 24m

Tom Verrilli, Chief Product Officer at Whatnot, argues that product management as a specialist function should be minimized, with PMs deployed only where truly needed. He advocates for empowering engineers and designers to make product decisions themselves, keeping senior PMs hands-on with IC work rather than managing layers of people, and leveraging AI to enable individual contributors to move faster with better context.

Summary

Tom Verrilli discusses Whatnot's unconventional approach to product management, built on the premise that "we regret that product management exists." This doesn't mean PMs are unnecessary, but rather that the proliferation of PMs in tech companies has infantilized engineers and designers by removing opportunities for them to develop decision-making muscles. Historically, product management emerged as a specialist role to manage scale when founders could no longer directly oversee all product decisions. However, Verrilli argues this has been taken too far—organizations now follow hiring ratios (one PM per six engineers) without questioning necessity.

At Whatnot, the team operates with just 22 PMs despite significant GMV, with assignments determined by actual needs rather than team structures. Rather than mapping PMs to engineering teams, they map PMs to problems and critical projects during biannual planning cycles. This allows flexibility—some engineering teams go without dedicated PMs for entire cycles while focusing on execution work that doesn't require PM guidance.

Verrilli emphasizes that PM is a trade, not a qualification—a skill developed through reps and practice. When PMs abstract engineers and designers from doing PM work, those teams lose the opportunity to develop these critical skills. The only argument for specialist product management is when you truly need dedicated focus on customer understanding, business context, and technical feasibility translation.

When hiring, Verrilli looks for systems thinking and macro-to-micro reasoning, but explicitly avoids candidates whose specialty is political alignment and stakeholder management rather than customer/technical insight. He received 31,832 applications over two years and hired one PM, indicating extremely high selectivity. Candidates trending down are those who discuss driving alignment and managing stakeholders; candidates trending up demonstrate both big-picture thinking and impatience to validate ideas quickly, with specific examples of building novel solutions rather than incrementally improving existing products.

A major shift Verrilli champions is moving senior PMs back to individual contributor work rather than management tracks. Historically, successful PMs got promoted into director roles managing other PMs, extracting top talent from actual product work. At Whatnot, VPs and directors still spend 90%+ of their time doing IC work. This enables faster decision-making—senior PMs with deep experience can make intuitive calls more quickly than coordinating across multiple junior PMs. It also creates natural cross-functional alignment; when the same person owns both discovery and ads, they naturally optimize for overall GMV rather than internal team politics.

Verrilli also discusses the importance of top-down leadership when leaders have genuine ground truth. He works with founders Grant and Logan at Whatnot who regularly clear their calendars to deep-dive into specific problems with teams, examining data and code directly rather than reviewing through layers. This sets cultural expectations that everyone seeks truth rather than playing politics. He distinguishes this from micromanagement—which fails when leaders lack ground truth—versus informed leadership that operates from the same data as teams.

On AI's impact, Verrilli argues the shift toward empowering individual contributors predates AI but AI accelerates it dramatically. Tools like Hex threads enable PMs to pull nuanced data cohorts and understand individual user behaviors without waiting for data scientists. Claude enables PMs to understand codebases, estimate LOE, and spot system interactions quickly. This means well-honed senior judgment combined with AI tooling creates enormous leverage for individual contributors.

Verrilli introduces the "play the accordion" mental model—constantly zooming in and out on problems. You stretch out (think deeply about implications), then compress (ship and iterate), learning from results to inform the next expansion cycle. This prevents both the trap of iterating locally without understanding broader impacts and the opposite trap of writing long strategic roadmaps that prevent rapid learning.

The discussion covers marketplace dynamics and why live commerce won't be displaced by agentic commerce. While agents handle high-intent purchases efficiently, most retail shopping is low-intent browsing. Live commerce recreates the social experience and human curation of physical retail at internet scale and convenience. Whatnot achieves this with different economics than entertainment platforms—a stream with 50 people is economically viable for sellers (comparable to a small retail store's foot traffic) whereas entertainment platforms require thousands for CPM economics.

Verrilli reflects on his Twitter experience (2015-16) during a chaotic period with nine heads of product in two years. Key lessons: Twitter had such strong product-market fit that organizational dysfunction couldn't kill it; and most organizational complexity isn't actually complexity, it's weak leadership avoiding hard decisions (like raising the character limit took 2+ years post-Verrilli despite universal agreement it was necessary).

On working with founder-led companies, Verrilli emphasizes the CPO role isn't about winning debates—it's about seeking truth alongside the founder. This requires understanding the founder's decision-making style, context they have that you might not, and picking battles wisely. When founders have made up their minds, the CPO's job is to understand why and help execute, not compete for vision.

About this episode

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 role3. What Tom looks for when hiring PMs4. The shift toward senior ICs doing the work5. How AI has transformed data science at Whatnot6. Tom’s “play the accordion” mental model7. Why “hire great people and get out of their way” fails8. His biggest lessons from his time at Twitter—Brought to you by:<a href="https://workos.com/lenny" target="_blank">WorkOS</a>—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more<a href="https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign" target="_blank">Mercury</a>—Radically different banking, now with Command—Episode transcript: <a href="https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management" target="_blank">https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management</a>—Archive of all Lenny's Podcast transcripts: <a href="https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0" target="_blank">https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0</a>—Where to find Tom Verrilli:• X: <a href="https://x.com/tdrobbo" target="_blank">https://x.com/tdrobbo</a>• LinkedIn: <a href="https://www.linkedin.com/in/tom-robertson-042" target="_blank">https://www.linkedin.com/in/tom-robertson-042</a>—Where to find Lenny:• Newsletter: <a href="https://www.lennysnewsletter.com" target="_blank">https://www.lennysnewsletter.com</a>• X: <a href="https://twitter.com/lennysan" target="_blank">https://twitter.com/lennysan</a>• LinkedIn: <a href="https://www.linkedin.com/in/lennyrachitsky/" target="_blank">https://www.linkedin.com/in/lennyrachitsky/</a>—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: <a href="https://www.whatnot.com" target="_blank">https://www.whatnot.com</a>• Building, and Whatnot: <a href="https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc" target="_blank">https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc</a>• Twitch: <a href="https://www.twitch.tv" target="_blank">https://www.twitch.tv</a>• Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): <a href="https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future" target="_blank">https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future</a>• Peter Bailis on LinkedIn: <a href="https://www.linkedin.com/in/pbailis" target="_blank">https://www.linkedin.com/in/pbailis</a>• Mike Krieger on LinkedIn: <a href="https://www.linkedin.com/in/mikekrieger" target="_blank">https://www.linkedin.com/in/mikekrieger</a>• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): <a href="https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next" target="_blank">https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next</a>• Ben Kus on LinkedIn: <a href="https://www.linkedin.com/in/benkus" target="_blank">https://www.linkedin.com/in/benkus</a>• Henry Shi on LinkedIn: <a href="https://www.linkedin.com/in/henrythe9th" target="_blank">https://www.linkedin.com/in/henrythe9th</a>• Hex Threads: <a href="https://hex.tech/product/threads" target="_blank">https://hex.tech/product/threads</a>• Product management theater | Marty Cagan (Silicon Valley Product Group): <a href="https://www.lennysnewsletter.com/p/product-management-theater-marty" target="_blank">https://www.lennysnewsletter.com/p/product-management-theater-marty</a>• Grant LaFontaine on LinkedIn: <a href="https://www.linkedin.com/in/grantlafontaine" target="_blank">https://www.linkedin.com/in/grantlafontaine</a>• Logan Head on LinkedIn: <a href="https://www.linkedin.com/in/logan-head" target="_blank">https://www.linkedin.com/in/logan-head</a>• Emmett Shear on LinkedIn: <a href="https://www.linkedin.com/in/emmettshear" target="_blank">https://www.linkedin.com/in/emmettshear</a>• Kara Swisher on X: <a href="https://x.com/karaswisher" target="_blank">https://x.com/karaswisher</a>• Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: <a href="https://www.youtube.com/watch?v=DcWqzZ3I2cY" target="_blank">https://www.youtube.com/watch?v=DcWqzZ3I2cY</a>• Star City on AppleTV+: <a href="https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1" target="_blank">https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1</a>• For All Mankind on AppleTV+: <a href="https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7" target="_blank">https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7</a>• Service NSW Mobile App: <a href="https://www.service.nsw.gov.au/services/service-nsw-mobile-app" target="_blank">https://www.service.nsw.gov.au/services/service-nsw-mobile-app</a>• Rudyard Kipling: <a href="https://en.wikipedia.org/wiki/Rudyard_Kipling" target="_blank">https://en.wikipedia.org/wiki/Rudyard_Kipling</a>• <a href="http://E-fish.com" target="_blank">E-fish.com</a>: <a href="https://www.e-fish.com" target="_blank">https://www.e-fish.com</a>—Recommended books:• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: <a href="https://www.amazon.com/dp/0062273205" target="_blank">https://www.amazon.com/dp/0062273205</a>• The Purpose Driven Church: Every Church Is Big in God’s Eyes: <a href="https://www.amazon.com/dp/0310201063" target="_blank">https://www.amazon.com/dp/0310201063</a>• Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: <a href="https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439" target="_blank">https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439</a>—Production and marketing by <a href="https://penname.co/" target="_blank">https://penname.co/</a>. For inquiries about sponsoring the podcast, email <a href="mailto:[email protected]" target="_blank">[email protected]</a>.—Lenny may be an investor in the companies discussed. To hear more, visit <a href="https://www.lennysnewsletter.com?utm_medium=podcast&utm_campaign=show-notes-no-free-preview-language">www.lennysnewsletter.com</a>

Key Insights

Verrilli argues that tech companies have over-hired PMs following mechanical ratio-based models (one PM per six engineers), infantilizing engineers and designers by removing their opportunity to develop decision-making skills through practice.
He claims that the proliferation of PMs is not inherently necessary and that organizations should deploy PMs only where specific problems require dedicated focus, rather than mapping them one-to-one to engineering teams.
Verrilli contends that product management is a trade (skill developed through reps) rather than a qualification, meaning engineers and designers can develop PM capabilities if given the opportunity and responsibility.
He asserts that candidates who specialize in political alignment and stakeholder management are undesirable; strong PM candidates should demonstrate customer insight, technical understanding, and bias toward rapid validation over consensus-building.
Verrilli argues that promoting successful PMs into management roles extracts top talent from hands-on product work, and instead senior PMs should remain in IC roles spending 90%+ of time on direct product decisions.
He claims senior PMs with deep experience can make decisions more quickly and often more correctly than coordinating across multiple junior PMs, because they understand how different systems interact and naturally optimize for overall business outcomes.
Verrilli argues that top-down leadership works well when leaders maintain genuine ground truth by regularly deep-diving into data and code alongside teams, distinguishing this from ineffective micromanagement based on incomplete information.
He contends that AI enables the shift toward IC-focused senior PMs by dramatically reducing the cost of understanding codebases, pulling nuanced data analysis, and estimating technical complexity without requiring engineers' time.
Verrilli claims that metrics revealing averages often hide important minority use cases and can lead to deprecating features that are 100% of value for specific customer segments, with cascading negative effects on those businesses.
He argues that live commerce serves a fundamentally different customer need than agentic commerce—capturing low-intent, browsing-oriented shopping that still dominates physical retail despite decades of e-commerce growth.
Verrilli claims that organizational complexity at struggling companies often stems from weak leadership avoiding hard decisions rather than actual technical complexity, using Twitter's character limit delay as an example.
He asserts that working effectively with product-minded founders requires the CPO to seek truth collaboratively rather than compete for vision, understanding the founder's context and picking battles strategically rather than fighting for every decision.

Topics

Product management organizational structureReducing PM headcount and specializationEmpowering engineers and designers in product decisionsIndividual contributor work for senior PMsHiring criteria for product managersAI's impact on product teams and decision-makingData-driven decision making and avoiding averagesTop-down versus bottom-up leadershipLive commerce and marketplace economicsWorking with founder-led companiesSystems thinking and the accordion mental modelThe difference between micromanagement and informed leadership

Transcript

As tech companies scaled, somewhere along the line, this HR ratio of a pod popped into being. Every time you hire six engineers, you add a designer, you add a PM. 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. Something you wrote online that surprised a lot of people, a whatnot product team, was built on the somewhat simple premise. We regret that product management exists. Not a thing you probably hear from a lot of people, a whatnot product team was built on the somewhat simple premise. We regret that product management exists. Not a…

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This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Summary

About this episode

Key Insights

Topics

Transcript

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