The Skip Podcast

This is the next episode in a series on what product management becomes when the AI hype meets real constraints. I sat down with three CPOs living about a year ahead of the rest of us: Sharmeen Chapp, Midjourney's first-ever product hire; Jiaona Zhang (JZ), CPO at Laurel; and Henrik Berggren, who runs product and design at Mutiny. Their teams are tiny on purpose, yet these are companies with years of history, paying customers, and enterprise contracts—not the frictionless blank slates that "AI-native" suggests. We get into who should actually be building, how customer signal should move through a company, and how each of them installed an AI-first operating system without tipping into theater.
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Key topics:
• What never changes in PM
• Laurel's "captain" model: everyone is a builder
• Zoning the codebase like a garden so everyone can build safely
• Making the whole company understand the customer
• The AI Operations team: pairing hackers with leaders
• Treating the AI transformation as a product, with employees as the users
• Moving at "Cheetah speed": sprint when the tools jump, then rest
• Current PMs are managing a fleet, not an empire
• Why the strongest leaders are going hands-on now
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Timestamps:
(00:00) Introduction
(03:30) Meet the three CPOs: Midjourney, Laurel, Mutiny
(08:45) Laurel's "captain" model: everyone is a builder
(13:03) Zoning the codebase like a garden
(17:19) Governing change when anyone can ship to production
(18:23) Sharmeen at Midjourney: installing product judgment
(21:53) Henrik on finding the line by stepping over it
(24:57) A Slack channel that pings on every meaningful action
(26:59) Running AI in public so skeptics convert
(29:29) The AI Operations team: pairing hackers with leaders
(32:15) Incentives, public systems, and evergreen context
(36:46) Managing context overload with distributed PM
(39:45) A user interview to shareable clips in 45 minutes
(45:16) First-party vs. third-party: what to build, what to buy
(47:34) The token-maximization "blip" and raising the floor
(49:31) Managing a fleet, not an empire
(53:40) "Cheetah speed": sprint when the tools jump, then rest
(56:37) Why the strongest leaders are going hands-on now
(57:29) Does the pendulum swing back to old-school PM?
(59:48) What never changes: business, customer, orchestration
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Brought to you by:
• Firecrawl—Power AI agents with clean web data
• Use code THESKIP for 10K free credits
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Referenced:
• Anthropic
• Cursor
• Devin
• Dropbox
• Dust
• GitHub
• Google Drive
• Grain
• Granola
• Laurel
• Meta
• Midjourney
• Mutiny
• Notion
• Procter & Gamble
• Slack
• Stripe
• Twitch
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Where to find Nikhyl:
• Twitter/X
• LinkedIn
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Where to find Sharmeen:
• Twitter/X
• LinkedIn
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Where to find JZ:
• Twitter/X
• LinkedIn
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Where to find Henrik:
• Twitter/X
• LinkedIn
–
Join The Skip:
• Skip Coach
• Skip Community
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
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Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you're interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

Kevin Yien is the Head of Product for Merchant Experiences at Stripe. Before that he led Product at Mutiny and Square. In this episode, Kevin and I discuss how to keep AI from becoming theater, why a PM shipping to production can be a red flag, and why AI is pulling product management back to its fundamentals of strategy, opinion, and judgment.
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Key topics:
• Why "PM is dead" is the wrong frame, and every function is "shifting left"
• The three PM archetypes, and how zero-to-one changed most
"Killing your darlings" and keeping the blast radius small
• From a personal knowledge corpus to a shared "team brain"
• The "floors and ceilings" of a shared knowledge base
• Why building 10 prototypes no one sees is just theater
• Writing as "clarity at scale," and why LLMs still can't do it
• Why vibe coding is a wasted learning opportunity unless you interrogate it
• The "eight and 80 test" for joy, pace, and hard family seasons
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Timestamps:
00:00 Introduction
03:40 What Kevin owns across Stripe's merchant experiences
05:24 Stop asking which role dies, focus on the outcomes
08:05 The three PM archetypes, and why zero-to-one changed most
10:50 Kill your darlings: keeping the blast radius small
14:30 The PM as the "arbiter of context"
17:55 Floors and ceilings of a shared "team brain"
20:43 "Does this obsolete me?" The PM layoff fear
22:50 Are wikis and knowledge artifacts back?
28:42 How Stripe incentivizes sharing: carrots over sticks
31:35 The pet peeve: 10 prototypes, zero users
35:20 Onboarding as a product: the first 100 days
38:16 Writing as "clarity at scale," and why LLMs still can't do it
45:35 The "piano scales" for a PM: forming an opinion
48:37 Do engineering-background PMs still win?
52:30 Are product, design, and engineering roles merging?
55:30 Joy, pace, and the "eight and 80 test"
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Brought to you by:
• Asana—The operating system for human agent teams
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Referenced:
• Andrej Karpathy
• Block
• Claude Code
• Contentful
• Dovetail
• GitHub
• Kevin on Lenny's Podcast
• Lindy effect
• Lovable
• Obsidian
• Patrick Collison
• Stripe
• v0
• Writer
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Where to find Nikhyl:
• Twitter/X
• LinkedIn
–
Where to find Kevin:
• Twitter/X
• LinkedIn
• Website
–
Join The Skip:
• Skip Coach
• Skip Community
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you're interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

Product pay is detaching from the old bands the way it did for AI researchers. In the past few weeks I've seen three offers go out to product executives at $10 million a year, and while almost nobody gets that number, it pulls the whole field up. The builder-executive who can build with modern tools and operate at scale now commands two to three times what the same profile did a year ago. In this episode, my co-host Carly Malatskey and I walk three real career decisions end to end: a leader worried the AI bubble will pop and playing it too safe, a consultant trying to become a product builder, and an elite executive trying to match joy, purpose, and income in one role. The throughline is the "Skip" question: not how to maximize today's job, but which next move opens the path to elite a few years out.
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Key topics:
• Why builder-executive pay detached from the bands
• The three questions every career-maximizer should ask themselves
• Thinking of constraints as a risk budget
• Why staying current beats the biggest job at the best company
• How to test whether a company is actually "current" from the outside
• Why top-of-market pay comes with strings, and how to sequence what you optimize for
• The mercenary vs. missionary approach

Timestamps:
(00:00) Introduction
(00:39) The 100-day shift: builder execs and $10M offers
(04:04) Case 1, Angie: two safe offers and an AI-bubble fear(05:04) Optimizing to be elite, or just to be prudent?
(06:58) Why a failed hot startup can leave you better off
(10:58) Thinking about what your next role sets up, not just the salary
(15:40) Case 2, Gary: Series A vs. Fortune 20
(16:36) Working backward from the PE operating-partner dream
(18:58) The biggest job at the most current company, not the best
(22:40) How to tell if a company is actually "current"
(25:26) Case 3, Monica: elite, comfortable, and chasing joy
(26:57) One more operating role, then founding
(29:33) Choosing mercenary over missionary
(35:26) Would the right company help her find a co-founder
(37:18) The three questions that shape modern career advice
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Brought to you by:
Asana—The operating system for human agent teams
–
Referenced:
• Anthropic
• Meta
• Microsoft
• OpenAI
• Stripe
–
Where to find Nikhyl:
• Twitter/X
• LinkedIn
–
Where to find Carly:
• LinkedIn
–
Join The Skip:
• Skip Coach
• Skip Community
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

Meta is one of the biggest dinosaurs in the park, yet in a matter of months it rebuilt PM top to bottom, and almost none of it was bought. My guest is Jagjit Chawla, a VP of Product at Meta who’s running a growing share of the Facebook app: Feed, Reels, and more recently Search. I worked alongside Jagjit for nearly ten years across Google, Credit Karma, and Meta, and almost nothing is as I remember it. These systems were built by the teams themselves, sometimes in a single evening, on tools you already have. Jagjit walks me through how a product org of a few thousand people learned to move like a startup again.
Key topics:
• Inside Meta’s “no-meeting week” that set the org loose on the tools
• The one job AI can't take: influencing other humans
• Why the PMs winning on Jagjit’s team aren't engineers
• What to do when you’re the bottleneck
• How to become an "AI captain"
• Triaging tens of thousands of bug reports with agents that validate and pre-write the fix
• Why letting AI write code made site incidents spike, and how Meta clamped down
• Building a morning brief that flags the decisions only you can make
• Why the management "compression algorithm" is dead and what replaced it
Timestamps:
00:00 Introduction
05:47 Why the biggest change is pace
07:29 From detailed PRDs to a paragraph, a prototype, and an eval set
09:32 Why the management "compression algorithm" is dead
10:37 Visibility is high, but synthesis is scarce
14:45 "Finding a scissor" when you don't have fancy tools
16:10 A morning brief that flags the decisions only you can make
22:37 When the agent quietly drops your source links
25:53 The one job AI can't take: influencing other humans
30:18 Getting an analyst's answer in five minutes, not 24 hours
33:33 Three ways AI changed the products, not just the process
37:25 Why letting AI write code made site incidents spike
40:39 The no-meeting week and the birth of "AI captains"
44:55 The world's largest Jenga game: why institutional knowledge wins
48:41 Why economics and physics PhDs are "out-PMing" engineers
52:14 Ideas and agency before tools
56:19 "AI lowers the floor and raises the ceiling"
58:40 Closing advice: once you taste it, you can't go back

Brought to you by:
• Glean—Work AI that works
• Framer—Design and build your website effortlessly with Framer Agents

Referenced:
• Claude Code
• Credit Karma
• Facebook
• Ferrari
• Gmail
• Google
• Google Chat
• Google Drive
• Indian Premier League (IPL)
• Instagram
• Meta
• Porsche
• Prince of Persia
• TikTok
• Workplace from Meta
• Zoom

Where to find Nikhyl:
• Twitter/X
• LinkedIn

Where to find Jagjit:
• LinkedIn

Join The Skip:
• Skip Coach
• Skip Community

Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

In today's episode, we work through five questions from leaders in the Skip community who are doing well by any measure: a director whose career keeps ending in short stints despite strong performance, a manager whose top performer turned adversarial, an exec fielding multiple outsized offers, a PM who does her best work with a great manager, and a first-time manager whose first report is more experienced than they are. In each case, the old playbook can't answer the real question.

Key topics:
• The "layoff merry-go-round": why short stints compound and what it actually takes to break the cycle
• Why the decision to found should only stay on the table if you're obsessed with a specific problem — not just bullish on AI
• How a sponsor-to-manager dynamic turns adversarial
• "Every superpower comes with a shadow", and what that means for the manager who created the monster
• Why some management relationships reach a graduation, and how to recognize when you're there
• The mercenary vs. missionary question: and why the person asking usually already knows their answer
• Why senior product leaders should remove "great manager" from their job search criteria entirely
• The pretzel framework: how to identify the culture where you have to “bend yourself” the least
• Why being "safe" as a manager matters more than matching your direct report's experience level

Referenced:
• Anthropic
• ChatGPT
• Claude
• Copilot
• Facebook
• Google
• Meta

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community

Brought to you by:
• Glean—Work AI that works
• Guru—Trusted knowledge for every AI tool and team

Where to find Nikhyl:
• Twitter/X
• LinkedIn

Where to find Carly:
• LinkedIn

Join The Skip:
• Skip Coach
• Skip Community

Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts

Timestamps:
00:00 Introduction
03:32 Finding the question behind the question
06:00 The director with three short stints weighing their next option
07:17 Breaking out of the "layoff merry-go-round"
14:37 Why founding should only stay on the table if you're truly obsessed
17:18 The manager whose top performer turned adversarial
18:41 How the sponsor-to-manager collision actually happens
24:48 "Every superpower comes with a shadow"
25:30 Why some management relationships reach a graduation
35:02 The exec fielding multiple offers and the question underneath
41:27 How to know you've earned the right to seek balance
46:50 Remove "great manager" from your job search checklist
51:17 The pretzel framework: find the culture where you bend least
57:20 The new manager whose first direct report is more experienced than them
58:25 Why being "safe" matters more than matching your report's credentials
1:02:40 "I don't need a bigger version of myself"


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com