The Skip Podcast

• The 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 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

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• The PM career framework for AI

  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

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• Why your career playbook expired: The new rules for 2025 job transitions

  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

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• Graduating Into Uncertainty? How to Actually Land Your First Tech Job

  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

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• The Mentor's Superpower: Pattern Recognition That Unlocks Careers

  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

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