The Skip Podcast

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
• Twitter/X
• LinkedIn

Where to find Ben
• LinkedIn

Where to find Janie
• LinkedIn

Where to find Julia
• LinkedIn

Join The Skip
• Skip Coach
• Skip Community

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

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.com

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:
• Twitter/X
• LinkedIn

Where to find Carly:
• LinkedIn
• She Leads Podcast
• Twitter/X

Join The Skip:
• Skip Coach
• Skip Community

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

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.com

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:
• Twitter/X
• LinkedIn

Where to find Carly:
• LinkedIn
• She Leads Podcast
• Twitter/X

Join The Skip:
• Skip Coach
• Skip Community

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

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:
Twitter/X
LinkedIn
Where to find Carly:
LinkedIn
She Leads Podcast
Twitter/X
Join The Skip:
Skip Coach
Skip Community
Find The Skip:
Website
Substack
YouTube
Spotify
Apple Podcasts
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.com

The old PM career playbook doesn’t work in the AI era. In this episode of The Skip, we lay out a new career framework for product managers, and it’s a lot more “choose your door” than “climb the ladder.” If you’re wondering whether to stay in big tech, jump to an AI startup, double down as a builder, or rethink your whole path, this one’s for you. We talk about why your hard-won product intuition is quietly becoming obsolete, why some ex-VPs are happily taking senior IC roles, and how to prepare for what’s coming next.
Key topics
• Why your product intuition is outdated — and how to “go back to school” without quitting your job
• Why company quality now matters more than your title, comp band, or level
• What elite AI companies are actually looking for in PMs
• The builder vs factory mindset: are you obsessed with the product, or with the machine that ships it?
• How to choose between Big Tech, hot AI startups, healthy growth companies, or founding
• A three-part reality check on constraints: compensation, location, and pace
• The truth about 9–9–6 and AI startups: when extreme pace is worth it, and when it’s just branding
• Why “coasting” in big tech is mostly a myth
• Remote vs hub tradeoffs: what you gain and lose by moving to SF or NYC
• Why this is Part 1 — and what we’ll go deeper on next in the PM Career Framework for AI series
Where to find Nikhyl:
• Twitter/X
• LinkedIn
Where to find Carly:
• LinkedIn
• She Leads Podcast
• Twitter/X
Join The Skip:
• Skip Coach
• Skip Community
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
Timestamps
(00:53) Why the PM career framework needs to be rewritten for AI
(03:35) Why ex-VPs are happily taking senior IC roles
(06:07) Why your current product intuition is becoming obsolete
(11:46) Why AI-first companies only want hands-on PMs
(14:40) How to choose between Big Tech, AI startups, growth companies, or founding
(18:06) How to actually upgrade your product intuition on the job
(25:13) What’s really happening with PM compensation in 2025
(33:46) Why true AI startups are rarely remote-first
(42:42) What 9–9–6 culture at AI companies actually looks like
(50:52) The myth of work–life balance in growth environments
(55:40) The builder vs factory mindset
(60:29) Are you obsessed with the product or the factory that ships it?
(67:11) The key takeaway for PMs making career moves in 2025
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.com