- 1 hour 2 minutesHow Meta Is Reinventing Product Management
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:
• Facebook
• Ferrari
• Gmail
• Google
• Meta
• Porsche
• TikTok
• Zoom
Where to find Nikhyl:
• LinkedIn
Where to find Jagjit:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com24 June 2026, 11:00 am - 1 hour 8 minutes5 Career Questions Your Old Playbook Can’t Answer
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:
• 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 [email protected]
Brought to you by:
• Glean—Work AI that works
• Guru—Trusted knowledge for every AI tool and team
Where to find Nikhyl:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
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.com10 June 2026, 2:00 pm - 59 minutes 21 seconds10 Job-Search Rules That Just Broke
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
• LinkedIn
Where to find Dana
• LinkedIn
Where to find Briana
• LinkedIn
Where to find Pei-Chin
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
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.com20 May 2026, 2:00 pm - 43 minutes 33 secondsThe product skill you must now master: Reinvention
If you're in a career transition right now and wondering whether you did something wrong, you didn't. Every question coming into Nikhyl.AI keeps circling the same idea: do I really have to reinvent? In today’s episode, Carly and I dive into four questions, from people in very different scenarios: A senior PM who feels her career’s gone backwards, an IC5 at a FAANG anchored by immigration constraints, a 50-year-old veteran a year into a job search, and a mid-career operator convinced he's hit a dead end. Each of them feels behind. None of them are. The whole industry is in a state of reinvention — if they'd reinvented five years ago, they'd be reinventing again today.
Key topics:
• Why the first stage of any transition is mourning, and why most people get stuck there
• The builder vs. manager divide: why "capital-P Product Managers" are thriving and "capital-M product Managers" are not
• Why proving to yourself and others that you’re a builder is the currency that keeps you alive in the next round of layoffs
• The uncanny valley of mid-to-late-career PMs and how you can climb out of it
• Why coaching, consulting, and advisory roles are shrinking careers in a world of rapidly-improving LLMs
• The “double-jump” job search strategy and why you should stop optimizing for the 10-year role
• How you can turn a non-PM background into a superpower with AI and product skills
Where to find Nikhyl
Where to find Carly
Join The Skip
Find The Skip
Timestamps:
00:00 Introduction
00:40 You're not behind, you're right on time
03:23 The senior PM who stepped backwards and lost her identity
04:36 Why "you're in mourning" is the first thing to say out loud
08:38 Builder vs. capital-M Manager: who the industry is actually hiring
12:28 The IC5 at a FAANG, the immigration clock, and infrastructure work
13:31 Why last year's "suck it up" advice stopped working
18:30 If you have builder instincts, you need to make sure people know about it
20:02 Navigating layoff season: Who should be worried and who should relax
23:02 The ageism reframe: Why a beginner's mentality beats pedigree
25:47 The 50-year-old veteran caught between coaching and "a real job"
27:29 Why coaching isn't a durable career in the LLM era
28:51 The "double jump" job-search strategy: get back in motion first
33:12 The mid-career operator who's convinced he's hit a dead end
35:30 Why being "non-technical" is no longer a blocker in 2026
36:09 How to reframe breadth of experience to form a power combination
39:03 "You didn't defer reinvention. You waited until now."
42:27 Embracing reinvention: First, mourn — then get back into motion
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com29 April 2026, 2:00 pm - 56 minutes 7 secondsWhat PM Hiring Managers Actually Screen For
Most interview advice tends to come from the candidate’s perspective - how to prep, share your experiences, and follow up. This conversation pulls back the curtain on the other side of the table. I spoke with hiring leaders from Netflix, Rippling, and EvenUp to learn how three great, yet operationally-different companies evaluate candidates. Surprisingly, all three leaders agreed on one core truth: most candidates are operating from a playbook that’s two years out of date. AI has upended the job-search landscape: old signals are table stakes, and the goal posts have changed.
Key topics:
• The new PM: Why companies are looking for candidates who “push the limits of what’s possible”
• The shift from behavioral to scenario-based questions
• Does pedigree still matter? Why trajectory is the new alternative signal for recruiters
• The three things that now separate a great take-home case study submission from a generic one
• Why case study presentations are still valuable - and help demonstrate core PM skills
• Whether website applications actually get looked at and why referrals are more binary than most people think
• How to signal drive and a frontier-pushing mindset when everyone claims to be a high performer
Where to find Nikhyl
• LinkedIn
Where to find McKenzie
• LinkedIn
Where to find Sam
• LinkedIn
Where to find Sarah
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
Timestamps
00:48 Introduction
04:12 Meet our guests from EvenUp, Rippling, and Netflix
09:06 How has the hiring process changed since COVID?
11:17 Is AI fluency explicitly tested in interviews?
12:42 Why quality and speed are favored over prioritization ability
16:16 Past experience vs. scenario questions—where the balance is shifting
19:52 Does pedigree still matter to hiring managers?
23:10 Why trajectory is an underrated signal to index on
26:43 Why the LinkedIn DM isn't dead
29:31 Does the take-home case study still hold value in the AI era?
33:21 Using case studies to screen for brevity, agency, and strategic thinking
39:09 Rippling's product discussion and panel case study process
43:52 Unpacking red flags in case study presentations
45:43 The collaboration test: curiosity vs. defensiveness under pressure
47:56 How to get noticed — are website applications even worth it?
50:56 Where EvenUp proactively sources candidates
53:00 Closing advice for mid-career PMs navigating today's job market
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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com15 April 2026, 2:00 pm - 1 hour 6 minutesHow to Navigate Org Drama
Work getting political isn't new, but surviving it without derailing your career has never been more challenging. As organizations flatten and restructures accelerate, the instincts that used to work — push back, demand clarity, make noise — often backfire. In this episode, we answer five questions from people caught in reorgs, managing-up dynamics, and situations where the "obvious" move turns out to be the wrong one.
Key topics
• What to do when leadership goes dark, and you can't tell if a reorg is coming
• The stay-vs-go framework: when brand matters, when comp overrides it, and why short tenures are more common than most people think
• The one question that puts your manager in an impossible position
• How to navigate an underperforming direct manager
• Why acting before a restructure is announced gives you a head start
• How to build the relationships you'll need on a rainy day before you actually need them
• What happens when VP sponsorship and calibration approval still aren't enough to get promoted
• How to start fresh on a new team when you're leaving a dysfunctional one behind
• The five-point playbook for navigating office politics without getting swept into them
References:
• Claude: https://www.claude.ai
• Floodgate: https://www.floodgate.com
• LinkedIn: https://www.linkedin.com
• Meta: https://www.meta.com
• OpenAI: https://www.openai.com
Brought to you by
• Framer—Build websites with enterprise needs at startup speeds: https://framer.link/dFacxBQ
• Customer.io—The customer engagement platform for human messaging: http://customer.io/skip
Where to find Nikhyl
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
Timestamps:
00:00 Introduction
03:18 Why organizational politics are so top of mind
04:59 “Everything’s changing, and no one’s telling me anything”
06:35 The two common reasons behind radio silence
12:41 Tough conversations shouldn’t be your first conversations
15:05 Why confrontation isn’t always the answer
17:35 Avoid putting your manager in a defensive position
22:12 Why role tenure is more malleable than you think
26:18 When a company reorg shifts you into a new role
29:55 How modern is your skillset?
33:57 How to identify whether burnout is worth it
40:03 Is the cost of your ambition future regret?
45:12 How to deal with an underperforming manager
55:23 Leaving a dysfunctional team for a new one
59:14 Drive impact first, talk long-term goals second
1:02:06 Why managers respond positively to specific goals
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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com1 April 2026, 12:00 pm - 57 minutes 45 secondsThe Post-IPO PM Playbook Is Being Rewritten
Most of the conversation about rebuilding product management comes from two ends of the spectrum: AI-first startups with 30 people and no real installed base, or big tech with thousands of PMs and decades of process. This episode is about the third category: companies that went public in the last few years, have real customers and revenue to protect, and are now trying to move like startups again. The CPOs of Hims & Hers, Rubrik, and Figma joined me to discuss what that actually looks like. Several of their findings directly contradict the advice you'd get from either end of the spectrum.
Key topics
• Why going public doesn't mean replacing your PM team with "business people"
• Why AI makes PM workload explode, not shrink
• What happens when engineering is no longer the bottleneck
• The skill Figma values most at scale (and why speed is the wrong thing to optimize for)
• Whether the IPO date is a real line in the sand—and why Yuhki and Anneka land in different places
• Why AI adoption at post-IPO companies requires the CPO to go first
• How Anneka wrote her team's Claude Code onboarding guide, opened the GitHub repos, and built a triage agent between meetings
• Why Dheerja joined Hims & Hers as the "AI Queen"
• Dheerja’s three-part AI framework she’s executing on
• Why Yuhki hired AI veterans first—then immediately hired people with no AI background at all
• The case against take-homes (and Anneka's idea for what should replace them)
• What a blank canvas reveals about a PM candidate that no case study or behavioral question can
• Why every PM is about to become a manager of agents
• How to talk to your team when the stock is down and you haven't announced anything new
• Why Figma deprecated annual planning—and what Yuhki thinks will become core PM work within a year
Where to find Nikhyl
• LinkedIn
Where to find Anneka
• LinkedIn
Where to find Dheerja
• LinkedIn
Where to find Yuhki
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:00) Anneka on leading from the top: visibly & vulnerably
(00:45) Intro: three CPOs, one inflection point
(05:53) How PM accountability shifts from startup to post-IPO
(07:24) The GM model: when PMs own P&L, not just product metrics
(10:54) Hiring systems thinkers over feature builders
(15:08) Where AI is actually moving the needle in enterprise B2B
(20:37) The three components of AI transformation
(24:13) How going public changes perception management at Figma
(27:00) Navigating stock drops and keeping teams focused
(30:30) Creating space for AI learning when the team is already maxed
(35:12) 3 steps to seeding AI teams
(40:03) How everyone is becoming a manager of agents
(44:34) Yuhki on resourcefulness and the blank canvas take-home
(47:40) Dheerja: go an hour deep on one real decision in the interview
(50:56) Why live pair Claude Code sessions is the future of PM interviews
(53:13) Predictions for 2026 and beyond
(55:34) Why it’s the best time in history to be a PM
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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com18 March 2026, 12:30 pm - 1 hour 1 minuteThree Job Searches, Three AI Roles: What Actually Worked
Most job search advice comes from people still in the thick of it—anxious, second-guessing, pattern-matching off too little data. This episode is different. We sat down with three product leaders who recently landed roles at Netflix, OpenAI, and Abridge, and did a full postmortem. What they shared upends a lot of conventional wisdom: the spray-and-pray pipeline doesn't work, your AI credentials matter less than you think, and the relationships that land jobs are often years in the making.
Key topics
• Why you need curiosity, not experience
• The "AI hungry" mindset: searching for environments that match your learning goals, not just your resume
• Why the best job search intelligence comes from people who just landed, not people still looking
• Why prototypes are now table stakes in take-homes
• How Janie built a shortlist of 5–10 companies in a week of 50–60 conversations
• Why Ben's Netflix role traces back to a cold application seven years ago
• What OpenAI's interview process actually looks like—and why it's less about the past than you expect
• Why most AI-native jobs aren't posted, and how to land them
• How to use investor attention as a proxy for company quality
• Why Ben's early interview mistake (not enough AI mindset) became the fuel for his take-home
Brought to you by
• Framer—Build websites with enterprise needs at startup speeds: https://framer.link/dFacxBQ
• Dust—The operating system for AI agents: https://dust.tt/skip
Where to find Nikhyl
• LinkedIn
Where to find Ben
• LinkedIn
Where to find Janie
• LinkedIn
Where to find Julia
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:00) How to prove your AI credentials
(04:42) Introducing the three product leaders
(06:00) Ben Dreier: from DoorDash to Netflix, the "AI hungry" move
(08:18) Julia Roberts: nine years at Pinterest, six months off, then OpenAI
(12:46) Janie Lee: going all-in on AI native at Abridge
(15:26) How to build a shortlist: 50–60 conversations in a week
(18:10) Ben's process: VC signals and insider conversations over job boards
(21:45) Cold outreach that actually works
(23:51) Ben: how curiosity, not networking, built his network
(25:14) Julia's different path: cold applies, inbound, and exec recruiters
(27:06) What exec recruiters are actually useful for
(30:30) Ben's Netflix backstory — tracing back to a cold apply seven years ago
(34:06) Staying connected with recruiters, coworkers, and people who said no
(41:10) What the OpenAI interview process actually looks like
(44:55) Authentic storytelling
(46:40) The Netflix take-home: how mid-process feedback became a turning point
(51:40) Janie: how to ace take-homes by using AI
(57:52) Julia’s final takeaway: know what you want before you search
(59:03) Ben’s final takeaway: follow the fun and genuine curiosity
(59:56) Janie’s final takeaway: high agency, high effort, put yourself in their shoes
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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com4 March 2026, 11:03 am - 52 minutes 26 secondsThe Promotion Mistakes That Derail PM Careers
It's promo season, and I've gotten roughly 1000 questions through nikhyl.ai—the pattern is unmistakable: people aren't just asking how to get promoted, they're asking whether the system is broken and whether they should quit over it. In this episode, we dissect five real questions from PMs who've been passed over. What becomes clear is the mistakes aren't in execution—they're in how people think about promotions in the first place. The tough reality is promotions are harder to get in this market. The question isn't whether you'll get promoted. It's how you respond when you don't.
Key topics
• Why promotions are harder now—and why that's not dysfunction
• The five-point framework for what to do when you don't get promoted
• The self-fulfilling prophecy that derails your career
• The one question that changes everything when you're passed over
• Why treating promotion as a game to win backfires
• The Peter Principle: why companies make you prove it before they promote you
• When "my career has flatlined" actually means you've hit the expected difficulty curve
• Why the skills that got you here won't get you there
• Why leadership might not be your destination—and that's okay
• The feedback gap: why your manager says you're great but leadership won't promote you
• Why leaving gas in the tank puts your career at risk
• Why you work for the company, not your manager
• What to do when your skip starts building a case against you
Brought to you by:
• Framer—Build websites with enterprise needs at startup speeds: https://framer.link/dFacxBQ
• Dust—The operating system for AI agents: https://dust.tt/skip
Where to find Nikhyl:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:00) Why you're not being promoted
(03:42) Why promo season brings more angst than any other time of year
(04:57) Question 1: L5 at Google denied promotion twice—is this organizational dysfunction?
(06:22) Why assuming your company is broken becomes a self-fulfilling prophecy
(09:50) What to do when there's literally no next-level job in your location
(11:45) Question 2: Six years at my company, seven rounds of interviews—still passed over for Executive Director
(14:06) The Peter Principle: why companies make you demonstrate next-level skills first
(17:18) Why promotion as a game to win is dangerous thinking
(21:12) When you've hit the ceiling—and that might be okay
(24:41) What to avoid when being passed over
(26:48) Question 3: I'm on track for promotion but political meetings drain my energy
(27:57) When the next level isn't for you—finding companies where leadership looks different
(32:11) Question 4: Three years since my last promotion to PPM—has my career flatlined?
(32:58) Why the IC-to-leader skill gap takes years to close
(35:50) The soft skills problem: leadership presence can't be taught in a class
(36:56) Question 5: My skip is suddenly giving me feedback my manager never mentioned
(38:42) Why you should never leave gas in the tank
(43:30) You work for the company, not your manager—why that matters
(45:25) The five biggest mistakes to avoid when you don't get promoted
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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com18 February 2026, 12:00 pm - 1 hour 25 minutesThe PM Career Framework for AI (Part 3): AI Labs to Founding
The "join a hot company" narrative gets even more complicated once you enter the AI-native part of the market. In Part 3 of our PM Career Framework for AI series, we close out with the doors everyone's obsessing over: AI labs, hot AI startups, ex-growth companies, and founding.
We unpack what these companies actually look for (spoiler: it's not "AI experience"), why hands-on builders win over managers, how location and pace become make-or-break constraints, and how to think about risk and chaos when the upside is real.
If you're trying to figure out whether you should stay put in 2026, or make the leap into the AI frontier, this episode breaks down the tradeoffs.
Key topics
• What AI labs are really hiring for (and why "productized research" is the core skill)
• Why AI labs want radically hands-on PMs, not managers
• Why Big Tech experience can become "inside-the-building skills" that don't translate
• Which companies expect 9-9-6 culture, and the self-selection problem it creates
• Why some struggling-company VP roles are still worth taking
• When equity becomes a psychological trap (and when to cut losses)
• Why remote leadership roles are rapidly disappearing
• The founder litmus test: why it's an emotional decision, not a spreadsheet decision
• The upside of founding even when it fails: the career story compounding effect
Where to find other the parts of this series:
• Part 1: https://theskip.substack.com/p/the-pm-career-framework-for-ai-how
• Part 2: https://theskip.substack.com/p/the-pm-career-framework-for-ai-part
Where to find Nikhyl:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:58) The “doors” framework: building a personal stack rank for AI
(04:57) The “productized research” skill: turning magic into product
(08:29) Why AI labs want hands-on builders, not managers
(15:00) Does AI domain expertise matter?
(19:14) Location constraints: The SF requirement for PM roles
(21:39) The Atlassian → OpenAI decision: Upending everything for the skip job
(30:16) Inside the high pace at AI Labs
(32:00) Hot AI Startups: the IC role that’s a step forward
(39:12) The 9-9-6 Reality: who's actually doing it
(41:59) The power years problem: Gender, biology, and self-selection
(46:13) The brand value of hot AI startups
(48:32) When equity becomes a psychological trap (and when to cut losses)
(54:12) Why some struggling-company VP roles are still worth taking
(58:53) Why remote leadership roles are declining
(63:10) The ex-growth equity risk: Why your compensation might never materialize
(65:24) Choosing between YC offer vs AI lab internship vs college
(73:41) The founder litmus test: why it's an emotional decision, not a spreadsheet decision
(80:24) When to join vs found
(82:31) Constraints + doors = your personalized career advice
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com8 January 2026, 12:00 pm - 1 hour 8 minutesThe PM Career Framework for AI (Part 2): The Large Tech Playbook
The “join a hot company” career narrative is getting a lot of PMs into trouble. In Part 2 of our PM Career Framework for AI series, we get practical: how to pick the door that fits you — and spot when a prestigious logo is quietly costing you career momentum. We break down nearly 600 listener questions, then map the first set of doors, from Big Tech and public enterprise to the “quality middle” of elite private companies and recent IPOs.
Key topics
• The “doors” framework: building a personal stack rank
• Golden handcuffs: when staying in Big Tech is rational
• Why L7+ doesn’t translate to startups or AI labs
• The “step down” that’s actually a level up
• How to know if you’re a fit for AI-native companies
• Debunking the myth of “coasting” in Big Tech
• Why APM programs can be the fastest way to learn the craft
• The stay/leave test: can you produce a career story?
• Who is suited to public enterprise tech
• The “quality middle” sweet spot
What’s next (Part 3):
Next episode, we assess the doors everyone’s obsessing over: AI labs (OpenAI / Anthropic), hot AI startups, ex-growth mid-stage companies, and founding. We will also cover why the rules change dramatically once you move into the AI-native part of the market.
Where to find Nikhyl:
Where to find Carly:
Join The Skip:
Find The Skip:
Timestamps
(00:46) The “doors” framework: building a personal stack rank
(11:50) Golden handcuffs: when staying in Big Tech is rational
(17:12) Why promotion often doesn’t translate to your next job
(19:29) The “step down” that’s actually a level up: from learning to teaching
(22:55) How to upgrade your product intuition without quitting your job
(26:23) The Big Tech fit test: why some builders struggle (and some thrive)
(31:03) Early-career exception: why APM programs can accelerate you
(34:26) Career stories: opinion → ship → impact → learning (and how to collect them)
(39:17) Public enterprise tech: when stability + liquidity is the smart move
(42:30) The hard question: are you unlucky, or are you the problem?
(48:44) If your company is behind on AI: be the change agent or move on?
(53:49) The “quality middle” sweet spot: elite teams, near-liquidity, durable brands
(57:55) Domain expertise vs “chasing AI”: where you’ll have the most impact
(62:17) Builder vs fixer: choosing the work you’re actually signing up for
(65:03) Key takeaways + what’s coming in Part 3
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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 [email protected]
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com11 December 2025, 12:00 pm - More Episodes? Get the App