The Skip Podcast

Nikhyl Singhal
  • 5.0 (71)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. And he coaches more than 100 executives, managers, and rising stars in navigating important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life. Subscribe to this podcast to hear from him and other executives as they teach unique career lessons. theskip.substack.com

  1. 12/11/2025

    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 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 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

    1h 8m

  2. 11/11/2025

    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 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 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

    1h 12m

  3. 09/04/2025

    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 companies What'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 stability Your 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 win Timestamps: (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 months 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 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 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

    1h 3m
  4. Graduating Into Uncertainty? How to Actually Land Your First Tech Job

    07/09/2025

    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/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 – 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 nikhyl@skip.community – 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

    1h 7m
  5. The Mentor's Superpower: Pattern Recognition That Unlocks Careers

    05/19/2025

    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 topics 6 common patterns holding leaders back How mentors can spot them, and what advice to give Breaking through organizational barriers Why smart people still get stuck Navigating change vs. waiting it out Thriving in early-stage chaos Why strong reviews don’t always lead to promotion Taking leadership roles before you feel ready Finding—and becoming—a great mentor How to ask better questions and get better advice – Where to find Carly: LinkedIn She Leads Podcast Twitter/X – Where to find Nikhyl: Twitter/X LinkedIn – 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. 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 – 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

    1h 20m
  6. Super Shadows | When Strengths Limit Growth

    03/26/2025

    Super Shadows | When Strengths Limit Growth

    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 topics The 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 nikhyl@skip.community – 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

    1h 5m
  7. Should you Stay or Go? A 5-factor framework for career-defining decisions

    02/27/2025

    Should you Stay or Go? A 5-factor framework for career-defining decisions

    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 nikhyl@skip.community – 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

    50 min
  8. The Insider's Guide to Tech Compensation, Negotiation, and Career Growth

    01/30/2025

    The Insider's Guide to Tech Compensation, Negotiation, and Career Growth

    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 dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking to understand tech compensation better, this episode offers practical insights for making informed career decisions. – Key topics: Why chasing comp early hurts career growthComparing job offersBreaking down key components of total compEnsuring you can exercise your sharesWhen and how to discuss salary expectationsMuch more– Referenced: Tech compensation: Beyond the offer letter– Where to find Carly: LinkedInShe Leads PodcastTwitter/X– Where to find Nikhyl: Twitter/XLinkedIn– Find The Skip: WebsiteSubstackYouTubeSpotifyApple PodcastsTikTok– 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 nikhyl@skip.community – Timestamps (00:00) Tactic for negotiating comp (01:54) Unpacking the mailbag format (03:09) Three job offers: which one should I take? (06:02) Understanding bonus structures (09:32) Why equity still matters today (17:38) Breaking the equity exit trap (25:29) Equity versus your market rate (30:37) Don't chase comp early on (34:12) Aligning the role to your superpower (37:47) Negotiating comp: Start with what matters most (47:30) When to discuss salary (51:49) Problems with averaged comp 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

    56 min
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5
out of 5
71 Ratings

About

The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. And he coaches more than 100 executives, managers, and rising stars in navigating important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life. Subscribe to this podcast to hear from him and other executives as they teach unique career lessons. theskip.substack.com

Information

  • Creator
    Nikhyl Singhal
  • Years Active
    2023 - 2025
  • Episodes
    42
  • Rating
    Clean
  • Copyright
    © Nikhyl Singhal
  • Show Website
    The Skip Podcast

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