This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)
· Summarized
Key takeaways
- Effective product management should be viewed as a muscle that needs consistent practice to develop, rather than a fixed qualification or role that fits all situations.
- AI significantly enhances productivity and decision-making in product teams by providing rapid insights, automating routine analysis, and enabling senior ICs to work independently rather than relying heavily on junior PMs or data scientists.
- Focusing on core product management skills—system thinking, understanding customer needs, and technical fluency—is crucial as automation and AI take on routine building tasks.
- Leadership in product requires deep involvement at the micro level—understanding code, customer behavior, and ground truth—to make better strategic decisions.
- The future of product teams may shift toward smaller, more autonomous roles with senior ICs taking on broader ownership, supported by AI tools and a culture of deep engagement with the actual product.
Summary
The Critique of Traditional Product Management
Tom Verrilli articulates a provocative stance that regrets the existence of traditional product management roles. He discusses how, as companies scale, the proliferation of PMs often infantilizes engineers and designers by creating a filter and babysitter role rather than empowering them to make decisions. He emphasizes that product management should be a muscle developed through practice, not a qualification that automatically fits every situation. Over-reliance on PMs can stifle the decision-making muscles of engineers and designers, leading to inefficiencies and a disconnect from ground truth.
AI's Impact on Product Roles and Data Science
Tom explores how AI enhances the capacity of individual contributors (ICs) and redefines productivity across product teams. Tools like Hex Threads and AI-driven data insights empower PMs and engineers to analyze data, spot regressions, and understand system behavior more rapidly. This shift reduces dependence on data scientists for routine analysis, allowing their skills to be focused on foundational data infrastructure improvements. AI accelerates decision-making, making it easier for senior ICs to operate independently and focus on impactful work, thus redefining the structure of product teams.
Managing Product Teams and Culture at Whatnot
The discussion reveals how Whatnot structures its product organization with loosely aligned PMs reassigned to different problems rather than fixed teams. This flexible approach allows PMs to tackle high-impact problems based on macro planning every six months. Verrilli advocates for senior ICs to do most of the work themselves rather than a traditional hierarchy where PMs spend their time in meetings or coaching. He underscores the importance of deep technical understanding, micro-level involvement, and staying close to ground truth, exemplified by leaders like his founder, Grant LaFontaine.
Skill Development and Hiring for the Future of Product Management
Verrilli shares insights on what qualities are now most valued in PM candidates—primarily system thinking and the ability to quickly assess and validate ideas. He notes a decline in the emphasis on stakeholder management and politics, favoring candidates who exude macro and micro thinking in case studies and interviews. He suggests that aspiring PMs should focus on honing core management skills—understanding customer, tech, and business—and actively engage in hands-on work to stay sharp.
The Evolution of Product Teams and the Role of Leadership
The conversation touches on how the future of product teams may look more fluid, with fewer dedicated PMs, engineers, and designers working more broadly across problems. Verrilli envisions a world where senior ICs, tech leads, or specialized individuals take the reins on projects, empowered by AI and a culture of ownership. Leadership at scale demands deep involvement, micro-level understanding, and a willingness to work in the weeds, which Verrilli believes leads to better decision-making and product quality.
Lessons from Twitter and Leadership Insights**
Reflecting on his experience at Twitter, Verrilli highlights the importance of simplicity, decisive leadership, and grounding decisions in ground truth. He advocates for leaders to immerse themselves deeply in the micro details, understand the code and customer experience firsthand, and avoid unnecessary complexity and delays caused by organizational inertia. His approach emphasizes trust, verification, and focusing on high-impact priorities, especially in founder-led companies.
Failure and Learning in a Career**
Verrilli candidly admits that he experiences failure often, emphasizing that relying on averages can be problematic when it overlooks crucial individual use cases. He argues for nuanced understanding of metrics and urges product people to prioritize ground truth and direct knowledge over superficial data signals. His philosophy underscores the importance of learning from failures through deep, detailed investigation and staying connected to real-world impact.
Sponsors
- WorkOS · Make your app enterprise-ready, with SSO, SCIM, RBAC, and more.
- Mercury · Radically different banking, now with Command.
Show notes
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:
• 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
Follow this show on AudioBrevity and new episodes get summarized for you. Create a free account