Three 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-homeBrought 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/skipWhere to find Nikhyl• Twitter/X• LinkedInWhere to find Ben• LinkedInWhere to find Janie• LinkedInWhere to find Julia• LinkedInJoin The Skip• Skip Coach• Skip CommunityFind The Skip• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps(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 shoesDon'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 youBrought 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/skipWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Carly:• LinkedIn• She Leads Podcast• Twitter/XJoin The Skip:• Skip Coach• Skip CommunityFind The Skip:• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps(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 promotedDon'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 effectWhere 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-partWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Carly:• LinkedIn• She Leads Podcast• Twitter/XJoin The Skip:• Skip Coach• Skip CommunityFind The Skip:• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps(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 spotWhat’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/XLinkedInWhere to find Carly:LinkedInShe Leads PodcastTwitter/XJoin The Skip:Skip CoachSkip CommunityFind The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTimestamps(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 3Don'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 seriesWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Carly:• LinkedIn• She Leads Podcast• Twitter/XJoin The Skip:• Skip Coach• Skip CommunityFind The Skip:• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps(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 2025Don'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

Career ladders aren't just changing—they're being demolished and rebuilt in real-time. In this emergency "weather report," Carly and I decode four career dilemmas that have completely flipped in the last six months. We explain why directors are taking IC roles (and thriving), why your Big Tech salary might be a golden trap, when to finally leave that stalled growth company, and why founding is suddenly on everyone's radar. If you're making any career move in 2025, your old playbook will hurt more than help.The New Career Math:• Why senior IC roles now trump management positions—and when stepping down is stepping up• The Big Tech paradox: 3x market comp but career stagnation (what's your breaking point?)• Ex-growth company reality: Why staying another month makes things worse• The founding surge: Why 8x more product leaders are starting companiesWhat's Actually Happening:• How AI and flat orgs killed the traditional ladder (and what replaced it)• What elite companies want now: hands-on builders, not ivory tower managers• The talent gravity effect: Why your coworkers matter more than your title• The "elite middle" strategy: Which companies offer both growth and stabilityYour Action Plan:• How to evaluate if you're becoming obsolete (and what to do about it)• The unnatural acts worth taking (hint: it involves a pay cut)• Six-month forecast: Where the opportunities will be and who will winTimestamps:(03:45) The rise of Super ICs(07:59) Why IC roles are considered premium(18:56) “I work at Google: should I stay, or should I go?”(27:05) How Nikhyl gives career advice to tech leaders(31:12) What are startups hiring for?(37:10) Why are more people leaving ex-growth companies?(42:21) Advice for choosing the right company to join(46:24) You need to work with great talent(48:21) How to navigate the wealth of career options(52:37) The career trap you need to avoid(56:29) Should you found a company?(59:09) Nikhyl’s forecast for the next six monthsWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Carly:• LinkedIn• She Leads Podcast• Twitter/XJoin The Skip:• Skip Coach• Skip CommunityFind The Skip:• Website• Substack• YouTube• Spotify• Apple PodcastsDon'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

In this episode, I’m joined by my co-host Carly Malatskey to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone who is — this episode is for you.–Key topics• Why your first job should feel like a sprint, not a stroll• How to tell if your job is setting you up — or holding you back• The truth about internships (they matter more than your degree)• How to stand out when applying — and why “spray and pray” fails• Why it’s okay (even smart) to view your first job as a stepping stone• Red flags and green flags once you’re hired• How to network in a way that doesn’t feel transactional• The mindset shift that separates top performers early in career• Why working in-person still gives you an edge• How to take real risks when you have the least to lose–Where to find Nikhyl:Twitter/XLinkedIn–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Join The Skip:Skip CoachSkip Community–Find The Skip:WebsiteSubstackYouTubeSpotifyApple Podcasts–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]–Timestamps(00:00) Why most grads feel lost — and what to do about it(01:44) How to navigate the 2025 job market(03:29) Why hustle still wins (yes, even now)(08:24) What to really look for in your first job(15:03) Why seeking feedback is a career unlock(17:30) Choose your boss — not the logo(20:02) Why taking risks early pays off later(28:35) How to tell a compelling career story(32:15) Job hunting that actually works(37:38) Making the leap from college to career(42:18) Why you should work while studying(46:13) How to maintain a network(55:10) Green flags and red flags once you’re hired(58:55) Your first job is a launchpad — not a life sentence(63:12) Final advice we wish we heard at 21 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’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others miss, and how you can use that insight to unlock your next move. Whether you're leading a team, switching paths, or just feeling off, this episode is packed with tactical advice for unlocking your career.–Key topics6 common patterns holding leaders backHow mentors can spot them, and what advice to giveBreaking through organizational barriersWhy smart people still get stuckNavigating change vs. waiting it outThriving in early-stage chaosWhy strong reviews don’t always lead to promotionTaking leadership roles before you feel readyFinding—and becoming—a great mentorHow to ask better questions and get better advice–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple Podcasts–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]–Timestamps(00:00) How to spot patterns(01:08) How to find and then become a mentor(10:57) Scaling mentorship(15:09) How to heat seek around patterns(21:47) Question 1: How can I break through organizational barriers?(22:29) Pattern 1: Are you actually stuck?(30:05) Question 2: How can busy leaders stay technically up to date?(30:28) Pattern 2: If you know what you should do, why aren’t you doing it?(42:48) Question 3: How to navigate change?(40:56) Pattern 3: Do you need to work on this problem, or just wait it out?(52:23) Question 4: How normal is chaos in early stage companies?(52:54) Pattern 4: Broken might be normal, and you were hired to solve problems(61:07) Question 5: My performance reviews are excellent, but why am I not being promoted?(61:41) Pattern 5: Are you growing faster than the company?(67:35) Question 6: Should I take a leadership role that I don’t feel ready for?(68:29) Pattern 6: Are you too humble or negative?(73:23) Key takeaways and summary(77:57) How to get in touch with Nikhyl 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’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to shifting expectations. Using a structured approach, we break down when to make a change, how to advocate for yourself, and how to evolve without losing what makes you successful. Whether you’re navigating subtle shifts or considering a big move, this episode helps you own your superpower—and the shadow that comes with it.–Key topicsThe unseen influence of Super ShadowsWhy past success won’t fuel future growthBreaking free from career stagnationThe power of self-advocacyHow top leaders seek feedbackIdentifying what actually needs to changeMuch more–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple Podcasts–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]–Timestamps(00:00) How your superpower can stall career growth(01:11) Show format(02:45) Listener question: Navigating a quiet career crisis(06:40) How to break free from feeling stuck at work(11:35) The case for self-advocacy in your career(16:36) Why past success won’t fuel future growth(19:48) Super Shadows: What they are and why they matter(30:46) When it’s time to confront your shadow(37:53) The risks of ignoring your shadow(40:56) How great leaders seek feedback(47:07) Pinpointing what actually needs to change(55:57) A strategy for sustainable career growth(57:04) Why change has to happen on the job(58:19) A real-world example from Nikhyl’s offsite(61:28) Key takeaways and final thoughts 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’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisions based on compensation, skills, lifestyle, long-term success, and work environment. Whether you’re considering a career move now or just want a structured way to assess future opportunities, this episode offers a practical guide to making confident job decisions.–Key topics:The Stay vs. Go framework for career decisionsHow to assess if your job is career additiveBalancing comp, skills, and lifestyle in job choicesThe probability of success matters in career movesHow long you should stay before making a switchAnd much more–Where to find Carly:LinkedInShe Leads PodcastTwitter/X–Where to find Nikhyl:Twitter/XLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple Podcasts–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]–Timestamps(00:00) The 5-factor framework(01:20) Mailbag question: “Should I stay or go?”(03:38) Is your job career additive?(09:52) Why tenure matters less for some people(15:51) Framework overview(17:21) How to think about compensation(21:28) Fishing for outlier comp offers(23:54) Don’t just optimize for comp(25:46) What skills are you picking up(30:09) How esoteric are your skills(32:37) Weighing up lifestyle(36:56) What’s the probability you will succeed?(42:03) Think about the environment you thrive in(44:54) Final 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