The Skip Podcast

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
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Where to find Kevin:
• Twitter/X
• LinkedIn
• Website
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Join The Skip:
• Skip Coach
• Skip Community
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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

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
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Referenced:
• Anthropic
• Meta
• Microsoft
• OpenAI
• Stripe
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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

In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding her own company. While the search itself continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways. All three reported feeling something I’ve started calling smiling exhaustion: working hard, going long, and surprised by how good it feels. If you're a senior leader, sitting in a stable role debating a move, weighing how you can ride the AI shift, or quietly wondering if founding finally belongs on your career path, this conversation is for you.

Key topics:
• How AI agents have flipped the first year at a new role from headwind to tailwind, and are even bringing joy to the first year of a new role
• The new founding math: fast, fun, and skill-additive, with a much lower downside than it used to be
• How to navigate the job search when you don’t live in San Francisco—and remote jobs are dwindling
• Why structured AI learning is the wrong move, and what to build instead, so your fluency is hard to fake
• How to signal hard boundaries to a new boss, and differentiate between real respect and performative virtue-signalling
• Why holding your professional identity loosely matters when the role of senior leader is getting reformatted in real time

Referenced:
• Airbnb: https://www.airbnb.com/
• Atlassian: https://www.atlassian.com
• Claude Code: https://claude.com/product/claude-code
• Harvey: https://www.harvey.ai
• Loom: https://www.loom.com
• Modern Animal: https://themodernanimal.com

Brought to you by:
• Guru—Trusted knowledge for every AI tool and team: https://www.getguru.com/?utm_source=the-skip&utm_medium=podcast&utm_campaign=skip-promo
• Customer.io—The customer engagement platform for human messaging: http://customer.io/skip

Where to find Nikhyl
• Twitter/X
• LinkedIn

Where to find Dana
• LinkedIn

Where to find Briana
• LinkedIn

Where to find Pei-Chin
• LinkedIn

Join The Skip
• Skip Coach
• Skip Community

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

Timestamps:
00:00 Introduction
04:08 Welcome, and why this is the second job-search postmortem
05:50 Meet Dana, Briana, and Pei-Chin
06:15 What the "smiling exhaustion" state is
09:58 Three career transitions, three different triggers
15:26 Has founding become a must-have on the modern career path?
17:09 Why "AI company" doesn't need to be a hard filter
21:43 The new founding math: Three-month traction windows and "everyone codes"
26:16 How AI agents flipped onboarding from headwind to tailwind
31:33 How to navigate the decline of remote-friendly roles
36:27 Setting hard family boundaries in the 996-company era
40:47 How proactive do senior leaders need to be to build their role pipeline?
43:10 Standing out to recruiters when your CV lacks traditional experience
47:43 Discovering Claude Code: "I felt like a sorcerer"
53:21 Why structured AI learning isn't necessary
57:21 When your resume doesn't fit the pattern, teach the interviewer
58:48 Closing wisdom: hold your identity loosely


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