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by Nikhyl Singhal
The Skip podcast helps tech professionals get ahead in their career. It's hosted by Nikhyl Singhal, a three-time founder, CPO, and product executive at Meta and Google. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. He now runs Skip Coach, a career service powered by the world's top CPO community, and has coached hundreds of product leaders through career decisions, management challenges, and transitions. Subscribe for career insights distilled from real coaching conversations. theskip.substack.com
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- 1 weeks ago1h 1m
Inside PM at Stripe: What Comes After "Become a Builder"?
Kevin Yien is the Head of Product for Merchant Experiences at Stripe. Before that he led Product at Mutiny and Square. In this episode, Kevin and I discuss how to keep AI from becoming theater, why a PM shipping to production can be a red flag, and why AI is pulling product management back to its fundamentals of strategy, opinion, and judgment. –Key topics:• Why "PM is dead" is the wrong frame, and every function is "shifting left"• The three PM archetypes, and how zero-to-one changed most"Killing your darlings" and keeping the blast radius small• From a personal knowledge corpus to a shared "team brain"• The "floors and ceilings" of a shared knowledge base• Why building 10 prototypes no one sees is just theater• Writing as "clarity at scale," and why LLMs still can't do it• Why vibe coding is a wasted learning opportunity unless you interrogate it• The "eight and 80 test" for joy, pace, and hard family seasons– Timestamps:00:00 Introduction03:40 What Kevin owns across Stripe's merchant experiences05:24 Stop asking which role dies, focus on the outcomes08:05 The three PM archetypes, and why zero-to-one changed most10:50 Kill your darlings: keeping the blast radius small14:30 The PM as the "arbiter of context"17:55 Floors and ceilings of a shared "team brain"20:43 "Does this obsolete me?" The PM layoff fear22:50 Are wikis and knowledge artifacts back?28:42 How Stripe incentivizes sharing: carrots over sticks31:35 The pet peeve: 10 prototypes, zero users35:20 Onboarding as a product: the first 100 days38:16 Writing as "clarity at scale," and why LLMs still can't do it45:35 The "piano scales" for a PM: forming an opinion48:37 Do engineering-background PMs still win?52:30 Are product, design, and engineering roles merging?55:30 Joy, pace, and the "eight and 80 test"–Brought to you by:• Asana—The operating system for human agent teams–Referenced:• Andrej Karpathy• Block• Claude Code• Contentful• Dovetail• GitHub• Kevin on Lenny's Podcast• Lindy effect• Lovable• Obsidian• Patrick Collison• Stripe• v0• Writer–Where to find Nikhyl:• Twitter/X• LinkedIn–Where to find Kevin:• Twitter/X• LinkedIn• Website–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. 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 nikhyl@skip.community This is a public episode. If you would like to discuss this with other s
- 2 weeks ago39 min
Builder-Executives Are Getting Paid Like Pro Athletes
Product pay is detaching from the old bands the way it did for AI researchers. In the past few weeks I've seen three offers go out to product executives at $10 million a year, and while almost nobody gets that number, it pulls the whole field up. The builder-executive who can build with modern tools and operate at scale now commands two to three times what the same profile did a year ago. In this episode, my co-host Carly Malatskey and I walk three real career decisions end to end: a leader worried the AI bubble will pop and playing it too safe, a consultant trying to become a product builder, and an elite executive trying to match joy, purpose, and income in one role. The throughline is the "Skip" question: not how to maximize today's job, but which next move opens the path to elite a few years out.–Key topics:• Why builder-executive pay detached from the bands• The three questions every career-maximizer should ask themselves• Thinking of constraints as a risk budget• Why staying current beats the biggest job at the best company• How to test whether a company is actually "current" from the outside• Why top-of-market pay comes with strings, and how to sequence what you optimize for• The mercenary vs. missionary approachTimestamps: Introduction The 100-day shift: builder execs and $10M offers Case 1, Angie: two safe offers and an AI-bubble fear Optimizing to be elite, or just to be prudent? Why a failed hot startup can leave you better off Thinking about what your next role sets up, not just the salary Case 2, Gary: Series A vs. Fortune 20 Working backward from the PE operating-partner dream The biggest job at the most current company, not the best How to tell if a company is actually "current" Case 3, Monica: elite, comfortable, and chasing joy One more operating role, then founding Choosing mercenary over missionary Would the right company help her find a co-founder The three questions that shape modern career advice–Brought to you by:Asana—The operating system for human agent teams–Referenced:• Anthropic• Meta• Microsoft• OpenAI• Stripe–Where to find Nikhyl:• Twitter/X• LinkedIn–Where to find Carly:• LinkedIn–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. 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 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
- Jun 24, 20261h 2m
How 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 itTimestamps:00:00 Introduction05:47 Why the biggest change is pace07:29 From detailed PRDs to a paragraph, a prototype, and an eval set09:32 Why the management "compression algorithm" is dead10:37 Visibility is high, but synthesis is scarce14:45 "Finding a scissor" when you don't have fancy tools16:10 A morning brief that flags the decisions only you can make22:37 When the agent quietly drops your source links25:53 The one job AI can't take: influencing other humans30:18 Getting an analyst's answer in five minutes, not 24 hours33:33 Three ways AI changed the products, not just the process37:25 Why letting AI write code made site incidents spike40:39 The no-meeting week and the birth of "AI captains"44:55 The world's largest Jenga game: why institutional knowledge wins48:41 Why economics and physics PhDs are "out-PMing" engineers52:14 Ideas and agency before tools56:19 "AI lowers the floor and raises the ceiling"58:40 Closing advice: once you taste it, you can't go backBrought to you by:• Glean—Work AI that works• Framer—Design and build your website effortlessly with Framer AgentsReferenced:• Claude Code• Credit Karma• Facebook• Ferrari• Gmail• Google• Google Chat• Google Drive• Indian Premier League (IPL)• Instagram• Meta• Porsche• Prince of Persia• TikTok• Workplace from Meta• ZoomWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Jagjit:• LinkedInJoin 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
- Jun 10, 20261h 8m
5 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 levelReferenced:• Anthropic• ChatGPT• Claude• Copilot• Facebook• Google• MetaDon'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 nikhyl@skip.communityBrought to you by:• Glean—Work AI that works• Guru—Trusted knowledge for every AI tool and teamWhere to find Nikhyl:• Twitter/X• LinkedInWhere to find Carly:• LinkedInJoin The Skip:• Skip Coach• Skip CommunityFind The Skip:• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps:00:00 Introduction03:32 Finding the question behind the question06:00 The director with three short stints weighing their next option07:17 Breaking out of the "layoff merry-go-round"14:37 Why founding should only stay on the table if you're truly obsessed17:18 The manager whose top performer turned adversarial18:41 How the sponsor-to-manager collision actually happens24:48 "Every superpower comes with a shadow"25:30 Why some management relationships reach a graduation35:02 The exec fielding multiple offers and the question underneath41:27 How to know you've earned the right to seek balance46:50 Remove "great manager" from your job search checklist51:17 The pretzel framework: find the culture where you bend least57:20 The new manager whose first direct report is more experienced than them58:25 Why being "safe" matters more than matching your report's credentials1:02:40 "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 <a href="
- May 20, 202659 min
10 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 timeReferenced:• 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.comBrought 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/skipWhere to find Nikhyl• Twitter/X• LinkedInWhere to find Dana• LinkedInWhere to find Briana• LinkedInWhere to find Pei-Chin• LinkedInJoin The Skip• Skip Coach• Skip CommunityFind The Skip• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps:00:00 Introduction04:08 Welcome, and why this is the second job-search postmortem05:50 Meet Dana, Briana, and Pei-Chin06:15 What the "smiling exhaustion" state is09:58 Three career transitions, three different triggers15:26 Has founding become a must-have on the modern career path?17:09 Why "AI company" doesn't need to be a hard filter21:43 The new founding math: Three-month traction windows and "everyone codes"26:16 How AI agents flipped onboarding from headwind to tailwind31:33 How to navigate the decline of remote-friendly roles36:27 Setting hard family boundaries in the 996-company era40:47 How proactive do senior leaders need to be to build their role pipeline?43:10 Standing out to recruiters when your CV lacks traditional experience47:43 Discovering Claude Code: "I felt like a sorcerer"53:21 Why structured AI learnin
- Apr 29, 202643 min
The 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 skillsWhere to find NikhylTwitter/XLinkedInWhere to find CarlyLinkedInJoin The SkipSkip CoachSkip CommunityFind The SkipWebsiteSubstackYouTubeSpotifyApple PodcastsTimestamps:00:00 Introduction00:40 You're not behind, you're right on time03:23 The senior PM who stepped backwards and lost her identity04:36 Why "you're in mourning" is the first thing to say out loud08:38 Builder vs. capital-M Manager: who the industry is actually hiring12:28 The IC5 at a FAANG, the immigration clock, and infrastructure work13:31 Why last year's "suck it up" advice stopped working18:30 If you have builder instincts, you need to make sure people know about it20:02 Navigating layoff season: Who should be worried and who should relax23:02 The ageism reframe: Why a beginner's mentality beats pedigree25:47 The 50-year-old veteran caught between coaching and "a real job"27:29 Why coaching isn't a durable career in the LLM era28:51 The "double jump" job-search strategy: get back in motion first33:12 The mid-career operator who's convinced he's hit a dead end35:30 Why being "non-technical" is no longer a blocker in 202636:09 How to reframe breadth of experience to form a power combination39:03 "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.com
- Apr 15, 202656 min
What 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 performerWhere to find Nikhyl• Twitter/X• LinkedInWhere to find McKenzie• LinkedInWhere to find Sam• LinkedInWhere to find Sarah• LinkedInJoin The Skip• Skip Coach• Skip CommunityFind The Skip• Website• Substack• YouTube• Spotify• Apple PodcastsTimestamps00:48 Introduction 04:12 Meet our guests from EvenUp, Rippling, and Netflix09:06 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 ability16:16 Past experience vs. scenario questions—where the balance is shifting19:52 Does pedigree still matter to hiring managers?23:10 Why trajectory is an underrated signal to index on26:43 Why the LinkedIn DM isn't dead29:31 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 thinking39:09 Rippling's product discussion and panel case study process43:52 Unpacking red flags in case study presentations45:43 The collaboration test: curiosity vs. defensiveness under pressure47:56 How to get noticed — are website applications even worth it?50:56 Where EvenUp proactively sources candidates53:00 Closing advice for mid-career PMs navigating today's job marketDon'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 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
- Apr 1, 20261h 6m
How 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 themReferences:• Claude: https://www.claude.ai• Floodgate: https://www.floodgate.com• LinkedIn: https://www.linkedin.com• Meta: https://www.meta.com• OpenAI: https://www.openai.comBrought 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/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 Introduction03:18 Why organizational politics are so top of mind04:59 “Everything’s changing, and no one’s telling me anything”06:35 The two common reasons behind radio silence12:41 Tough conversations shouldn’t be your first conversations15:05 Why confrontation isn’t always the answer17:35 Avoid putting your manager in a defensive position22:12 Why role tenure is more malleable than you think26:18 When a company reorg shifts you into a new role29:55 How modern is your skillset?33:57 How to identify whether burnout is worth it40:03 Is the cost of your ambition future regret?45:12 How to deal with an underperforming manager55:23 Leaving a dysfunctional team for a new one59:14 Drive impact first, talk long-term goals second1:02:06 Why managers respond positively to specific goalsDon'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 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
About The Skip Podcast
The Skip podcast helps tech professionals get ahead in their career. It's hosted by Nikhyl Singhal, a three-time founder, CPO, and product executive at Meta and Google. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. He now runs Skip Coach, a career service powered by the world's top CPO community, and has coached hundreds of product leaders through career decisions, management challenges, and transitions. Subscribe for career insights distilled from real coaching conversations. theskip.substack.com
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