🧠 _

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 [email protected].

—

Lenny may be an investor in the companies discussed.

Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech.

In our in-depth conversation, we discuss:

1. Inside today’s “tale of two cities” talent market

2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires

3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit

4. The worst question to ask when sourcing great talent

5. The rise of the forward deployed engineer—and how to become one

6. The biggest mistake founders make when hiring their first recruiter

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Where to find Adam Ward

• X: https://x.com/wardadamp

• LinkedIn: https://www.linkedin.com/in/adampward

—

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

(03:01) The state of the hiring market

(06:41) What roles are trending up and what roles are trending down

(11:25) The three-step hiring framework that changes everything

(21:58) Getting the right people to actually respond

(25:42) Keeping talent a top priority

(29:16) Inside Cursor’s recruiting operation

(32:19) How to relentlessly pursue top talent

(35:42) “Caring is free”

(38:33) The conversation most companies underestimate

(39:19) Rethinking the atomic unit of a search

(40:12) Other recruiting tactics

(45:04) What the on-site is really for

(49:35) The importance of work trials

(53:10) The offer stage

(57:53) Negotiations and comp

(01:01:50) The details that actually close the deal

(01:07:23) What it’s like working with an exec team who values recruiting

(01:09:42) Talent density

(01:11:18) The first recruiting hire most founders get wrong

(01:15:00) Building incredible teams

(01:18:12) The time between offer and acceptance

(01:19:48) What’s next for the recruiting function

(01:21:00) Lightning round

—

Referenced:

• Cursor: https://cursor.com

• Trilogy: https://trilogy.com

• Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724

• Inside Cursor: https://colossus.com/article/inside-cursor

• SpaceX: https://www.spacex.com

• Joe Gebbia’s website: https://joegebbia.com

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

• Granola: https://www.granola.ai

• Wispr Flow: https://wisprflow.ai

• 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch

• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working

• The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham

—

Recommended books:

• Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

Sonali Varde, Senior Software Engineering Manager at LinkedIn, joins host Kanchan Shringi to discuss how AI is changing the role of the engineering manager. They explore how AI is showing up in day-to-day management work, including operational reviews, planning, communication, workflow automation, and preparation for leadership discussions.

The conversation looks at how engineering teams are adopting AI tools and agents, what kinds of skills and practices are becoming more important, and how managers can think about context, review, testing, and operational rigor as AI-assisted development becomes more common. They also discuss how AI affects coaching, performance conversations, hiring, onboarding, team composition, and collaboration with peers and leadership. The episode considers both the opportunities and limits of AI for engineering management, with attention to human judgment, curiosity, ownership, and the continuing importance of technical and organizational understanding.

Richard Rumelt is a legend in the world of strategy. He’s the author of Good Strategy/Bad Strategy and The Crux: How Leaders Become Strategists, both of which are often recommended by guests on this podcast. From his early days teaching in Iran at a Harvard-sponsored business school to teaching at Harvard Business School itself to over four decades teaching at UCLA’s Anderson School of Management, Richard’s impact resonates globally. His strategic insights are sought after by major corporations including Microsoft, Shell, Apple, AT&T, Intel, and Commonwealth Bank and by governmental organizations such as the U.S. Army Special Operations Command. In this episode, we discuss:

• The essential components of a good strategy

• The importance of coherence in strategy

• Common pitfalls that create a bad strategy

• How “power” plays into strategy, and common sources of power

• The value of knowing history when developing effective strategies

• Why a strategy should simply be called an “action agenda”

• The need for one decider in an organization

—

Brought to you by:

• CommandBar—AI-powered user assistance for modern products and impatient users

• Miro—A collaborative visual platform where your best work comes to life

• Vanta—Automate compliance. Simplify security.

—

Find the full transcript at: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

—

Where to find Richard Rumelt:

• Email: [email protected]

• LinkedIn: https://www.linkedin.com/in/richard-rumelt-18520828/

• Website: https://thecruxbook.com/

—

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) Richard’s background

(04:29) What is a strategy?

(06:23) The essential components of a good strategy (the “kernel”)

(15:04) An example of good strategy

(16:55) Bad strategy

(25:17) The importance of focus and power

(28:19) Identifying and utilizing power

(34:38) Types of power

(41:13) Implementing power

(48:15) The importance of historical knowledge

(55:23) How to write an action agenda

(01:02:47) The crux

(01:10:40) Challenges to executing a strategy

(01:15:44) The need for a decider

(01:20:39) Strategy for startups

(01:26:04) Richard’s “value denials” exercise

(01:31:01) Closing thoughts

(01:33:57) Lightning round

—

Referenced:

• China’s Xi says ‘reunification’ with Taiwan is inevitable: https://www.cnbc.com/2023/12/31/chinas-xi-says-reunification-with-taiwan-is-inevitable.html

• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240

• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

• Fundamental Issues in Strategy: A Research Agenda: https://www.amazon.com/Fundamental-Issues-Strategy-Research-Agenda/dp/0875843433/

• Strategy, Structure, and Economic Performance: https://www.amazon.com/Strategy-Structure-Economic-Performance-Richard/dp/0875841090

• There’s more than the CIA and FBI: The 17 agencies that make up the U.S. intelligence community: https://www.latimes.com/nation/la-na-17-intelligence-agencies-20170112-story.html

• Programme for International Student Assessment: https://www.oecd.org/pisa/

• Gerstner: Changing Culture at IBM—Lou Gerstner Discusses Changing the Culture at IBM: https://hbswk.hbs.edu/archive/gerstner-changing-culture-at-ibm-lou-gerstner-discusses-changing-the-culture-at-ibm

• Marvin Lieberman on LinkedIn: https://www.linkedin.com/in/marvin-lieberman-2a6b72/

• S&P 500: https://www.spglobal.com/spdji/en/indices/equity/sp-500/#overview

• Battle of Tora Bora: https://en.wikipedia.org/wiki/Battle_of_Tora_Bora

• Milton Friedman: https://en.wikipedia.org/wiki/Milton_Friedman

• The Louvre: https://www.louvre.fr/en

• How does SpaceX build its Falcon 9 reusable rocket?: https://www.sciencefocus.com/space/how-does-spacex-build-its-falcon-9-reusable-rocket

• Charles Darwin: History’s most famous biologist: https://www.nhm.ac.uk/discover/charles-darwin-most-famous-biologist.html

• Donald Rumsfeld: https://www.defense.gov/About/Biographies/Biography/Article/602800/

• Bush: The Decider-in-Chief: https://www.cbsnews.com/news/bush-the-decider-in-chief/

• Woodrow Wilson: https://www.whitehouse.gov/about-the-white-house/presidents/woodrow-wilson/

• How the Sinking of Lusitania Changed World War I: https://www.history.com/news/how-the-sinking-of-lusitania-changed-wwi

• Nokia: https://www.nokia.com/

• The Rise and Fall of Nokia: https://www.hbs.edu/faculty/Pages/item.aspx?num=46041

• Salesforce: https://www.salesforce.com/

• These New Windows Let the Summer Breeze In, But Block the Street Noise: https://www.smithsonianmag.com/smart-news/these-new-windows-let-the-summer-breeze-in-but-block-the-street-noise-7906121/

• Stop it! (Bob Newhart): https://www.youtube.com/watch?v=jvujypVVBAY

• The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1982176865

• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821

• Titan: The Life of John D. Rockefeller, Sr.: https://www.amazon.com/Titan-Life-John-Rockefeller-Sr/dp/1400077303/

• Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone

• Smart telescopes: https://milehighastro.com/collections/smart-telescopes

• Cassandra Clare: https://cassandraclare.com/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

Richard Rumelt is a legendary strategy pioneer and author of The Crux and Good Strategy Bad Strategy. In this episode, Rumelt dismantles traditional "strategic planning," arguing it is often merely a financial budget masquerading as actual business strategy. 

He emphasizes that true strategy is problem-solving rooted in rigorous diagnosis. Discover how to identify the crux while breaking through unconscious constraints to achieve coherent, highly impactful, and addressable strategic organizational action. 

If your leadership is discussing which AI tool to buy, they are having the wrong discussion.Barbara Lampl has built and fixed data and AI strategies for over 20 years. Behavioral mathematician, known on LinkedIn as AI Babsi. Her diagnosis of failed AI adoption is blunt: organizations refuse to redesign their processes, and the knowledge that actually runs the business was never written down.What you'll hear:- Why every process needs touching before an LLM goes near it- How to capture tribal knowledge before your experts retire, and why exit interviews never work- RAG as an umbrella term: when vectors are enough, when you need a graph, and the six-month trade-off between them- The token math of file formats: PowerPoint costs a factor of 9 to 13, markdown wins- Her take on the Claude Fable 5 re-rollout and why Europe has no Anthropic of its own- The first step for a leadership team stuck in tool discussions: C-level trainingLinks:Barbara on LinkedIn: https://www.linkedin.com/in/barbaralampl/The Data AI Institute: https://www.data-ai-institute.comMore episodes & all platforms: https://stellarwork.start.pageNewsletter: https://substack.com/@stellarworkHost: Ben, founder of Stellar Work

The New New Thing by Michael Lewis is the story of entrepreneur and computer scientist Jim Clark, the heady days of the 1990s .com bubble, and the companies he started. Namely, Silicon Graphics, Netscape, and Healtheon. Written in 1999, it captures a particular era in Silicon Valley, including the unbridled enthusiasm of venture capitalists and startup-stock compensated software engineers thinking they can change the world at every turn. In this episode we’ll discuss the book, the time, the place, and the man, Jim Clark.

Follow us on X, Facebook, and YouTube.

Edited by Giacomo Guatteri

Find out more at https://businessbooksandco.com

Read transcript

This episode covers the unique way Larry Ellison thinks.

I spent over 40 hours reading (and rereading) this book on Ellison written by Matthew Symonds. ⁠

I then spent several days editing down 40 pages of notes into a one-hour nonstop stream of Larry Ellison's ideas.

Episode sponsors:

⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠ gives you everything you need to control spend, watch your costs, and optimize your financial operations —all on a single platform. Make history's greatest entrepreneurs proud ⁠⁠⁠by going to Ramp and learning how they can help your business control your costs and save time and money.⁠⁠⁠ ⁠⁠⁠⁠https://ramp.com⁠⁠⁠⁠

Automate compliance, security, and trust with Vanta.⁠ ⁠⁠⁠⁠Vanta helps you win trust, close deals, and stay secure—faster and with less effort⁠⁠⁠⁠⁠. ⁠⁠⁠Find out how increased security leads to more customers by going to Vanta⁠⁠⁠. Tell them David from Founders sent you and you'll get $1000 off. ⁠⁠⁠https://www.vanta.com/founders⁠⁠ ⁠⁠⁠

⁠Collateral⁠⁠ transforms your complex ideas into compelling narratives⁠. Collateral crafts institutional grade marketing collateral for private equity, private credit, real estate, venture capital, family offices, hedge funds, oil & gas companies, and all kinds of corporations. Storytelling is one of the highest forms of leverage and you should invest heavily in it. You can do that by going to ⁠⁠https://collateral.com

Kelly Johnson’s “14 Points” read like a SpaceX operations manual — 60 years before SpaceX was founded. Kelly Johnson created Skunk Works, which he defined as: “A concentration of a few good people solving problems far in advance—and at a fraction of the cost—of other groups by applying the simplest, most straightforward methods possible to develop and produce new projects. All it is really is the application of common sense to some pretty tough problems.”

Kelly Johnson was a great engineer and system builder with genius for organizational design. His autobiography which he wrote when he was 75 years old is full of hard-earned wisdom from his 44 year career.

This episode is what I learned from reading Kelly: More Than My Share of it All by Kelly Johnson.

Made possible by:

What I learned from reading Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel and Blake Masters (for the 3rd or 4th time)

Made possible by: