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In this episode, three leaders who recently took on AI roles break down their job search: Anthony Maggio, who left Airtable after five and a half years to become CPO at Runway, Gadi Ben-Zvi, who leads AI platform and products at Eli Lilly, and Chandra Raghavan, a principal PM on Search AI at Google. This is the third conversation in our job-search series, where about every 100 days I check in with executives who just landed new roles to see what has changed. We get into why Anthony passed on the frontier labs for a 200-person company, why Gadi joined Eli Lilly, a company willing to spend years on its AI bets, and why Chandra says choosing between a startup and big tech is “a false dichotomy.”  – Key topics: • The interview questions that test AI judgment, starting with "Where did it fail?" • Why a side project of your own became the credential • How to avoid becoming "the person who tried ChatGPT in 2022" • Why a senior IC role on Google Search AI feels more like a startup than big tech • How to tell if a company has a real edge in AI • What hasn’t changed in senior PM interviews, and the new baseline • What to stop highlighting: managing through layers and cross-functional coordination • How candidates stand out now: auditing the product and prototyping fixes after a first conversation  – Timestamps: 00:00 Introduction 02:58 Meet the three leaders who just landed AI roles at Lilly, Runway, and Google 09:19 Anthony's search criteria: proximity to the frontier, talent density, and fit 14:30 How research breakthroughs become products at Runway 15:57 Why a 200-person company beat the big labs 19:32 What Eli Lilly built with 150 years of data, and why the bet will last 23:09 Optimizing for 2026 Chandra, not 2016 Chandra 26:05 Startup-style ownership at scale: Chandra's "false dichotomy" 29:08 What surprised them about interviews 33:44 How to speak credibly about agents when your job doesn't build them 39:44 What Eli Lilly wanted from a product leader with no pharma background 41:20 The questions interviewers are asking about AI 43:10 Why continuous experiments beat one big project 48:31 What past experience still counts, and what to stop highlighting 50:31 How candidates stand out now: auditing the product and prototyping fixes after a first conversation 52:58 Finding a company's real edge: proprietary data, domain expertise, feedback loops 56:23 How Google Search moves like a startup, and why you onboard yourself –  Brought to you by: • Chargebee—Billing and monetization infrastructure for the AI era • Stripe Treasury—Bring payments and finances together  – Referenced: • 10 Job Search Rules That Just Broke • Airtable • Airtable Omni and Field Agents • Anthropic • ChatGPT • Claude • Eli Lilly • Google • Google AI Mode • Google AI Overviews • Google Photos • Meta • OpenAI • Runway • Runway Solaris • Three Job Searches, Three AI Roles  – Where to find Nikhyl: • Twitter/X • LinkedIn –  Where to find Anthony: • Twitter/X • LinkedIn  – Where to find Gadi: • LinkedIn  – Where to find Chandra: • 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 [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

What do the hottest companies look for when they hire a CPO or head of product? I put the question to three people who sit in these searches every week: Lindsay Keith of Daversa, Andrew Abramson of Fusion Talent, and Caroline Horn of a16z. We had a similar conversation in January 2026, and the market has moved a lot since. A year ago, founders wanted a narrow profile: a former founder, hands-on, willing to work 9-9-6 hours. That profile hasn't gone away fully, but as companies mature past their first head of product, founders increasingly know what they want. The winning profile is the executive builder: someone senior enough to run the function and still close enough to the work to build. – Key topics: • Why founders want senior leaders who never stopped building • Why "go be an IC" stopped applying to executive searches about six months ago • Staying "close to the metal": how companies test whether an executive is really hands-on • Why working sessions with the team have replaced the take-home presentation • The attributes that matter more than the title • Why technical depth is now a must-have for product leaders • In-office expectations, and why 9-9-6 went quiet but didn't disappear • Comp as a pressure cooker • Why AI fluency will be table stakes by next summer, and what will differentiate candidates instead – Timestamps 00:00 Introduction 02:28 Meet our guests from Daversa, Fusion Talent, and a16z 04:58 How much has demand for product leaders grown this year? 06:14 The two types of companies hiring a CPO right now 09:34 Why founders under-hired and are now up-leveling the role 12:15 How companies assess whether an executive is really hands-on 14:25 Working sessions have shifted from presenting to building together 18:00 The profile of candidates closing searches in the last 90 days 20:50 Why later-stage companies want builders who can attract AI-pilled PMs 23:30 Should executives found a company to boost their careers? 25:00 The attributes that matter 27:10 Do AI companies need leaders with AI experience? 31:04 Building AI reps outside your day job 33:08 In-office expectations and whether 9-9-6 has cooled 35:15 Can executives with families keep up with the pace? 39:12 How to assess a company's culture before you join 44:25 How to evaluate a paper-rich offer at a high valuation 49:05 Competing with Meta, Google, and the labs on comp 51:58 Predictions for next summer: researchers, physical AI, and technical depth 56:18 Why AI fluency will stop differentiating candidates 57:24 Domain depth as the next differentiator – Referenced: • a16z • Abridge • Airbnb • Airtable • Anthropic • Atoms • Autodesk • Bending Spoons • ChatGPT • Claude • Cursor • Datadog • Daversa • Decagon • DoorDash • Figma • Fusion Talent • Google • Gusto • Harvey • Meta • Miro • Nash • OpenAI • Sharp Performance • Sierra • Square • Substack • Travis Kalanick • Uber • Vercel • xAI – Brought to you by: • Chargebee—Billing and monetization infrastructure for the AI era – Where to find Nikhyl • Twitter/X • LinkedIn – Where to find Lindsay • LinkedIn – Where to find Andrew • LinkedIn – Where to find Caroline • 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 [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, Tulsee Doshi, who leads product for Google's Gemini models, joins me for the fourth conversation in the "Inside PM" series. Tulsee has spent eleven years at Google, moving through Search and YouTube before taking on product for the Gemini family and Google's video, image, and audio models. We get into how her team avoids building a boring product, why their blend of platform work and lab work feels like a new kind of product management, and what she looks for in the PMs she thinks will thrive in that environment. – Key topics: • Why customer requests get weighed against research the customers can't see • Why stack-ranking every request would leave you with a boring product • The 20 prompts trick for turning a vague ask into a great eval • How to know a model is ready to ship without waiting a year • Reading a model's "vibes," and why Simon Tokumine's gut check carries real weight • Prototyping features that don't work yet on purpose • Why "technical" on her team means thorough, not a computer science degree • The Nano Banana moment that "fuels all of the other chaos" – Timestamps: 00:00 Introduction 03:28 Welcoming Tulsee Doshi to break down how Google builds Gemini 04:10 Eleven years at Google, from Search and YouTube to leading Gemini 06:20 Why the model team works like an engine maker for a garage of cars 08:40 Why stack-ranking every request would produce "a boring product" 11:25 "Nothing can replace a great eval": evals as the new PRD 14:36 The "20 prompts" trick for turning a vague ask into a great eval 18:44 How to know a model is ready to ship without waiting a year 22:40 "Vibes": why Simon Tokumine's gut check on a model carries real weight 27:20 Why speed beats trying to build the perfect product today 29:35 Prototyping features that "don't quite work yet," on purpose 31:05 The 60/20/20 rule for building against a model that keeps improving 33:58 The five traits she looks for in a research PM 40:35 Why "technical" on her team means thorough, not a CS degree 44:25 How AI tools are changing what Google's PMs do all day 48:30 Why Google's I/O still matters as a forcing function 52:50 The vibe inside Gemini right now: hype and chaos at once 55:20 What she'd change running product outside a model lab 57:15 The Nano Banana moment that "fuels all of the other chaos" – Brought to you by: • Chargebee—Billing and monetization infrastructure for the AI era – Referenced: • Antigravity • Gemini • Gemini Deep Research • Gemini Notebook • Gmail • Google • Google Cloud • Google's Associate Product Manager (APM) Program • Inside PM at Meta • Inside PM at Meta 2 • Inside PM at Stripe • Inside PM at Waymo • Nano Banana • Simon Tokumine – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Tulsee: • Twitter/X • 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 [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, Jagjit Chawla, the VP who runs Facebook's Feed and Reels, returns to see how his predictions from our June conversation have landed. Back in the spring, he described Meta as a company racing to turn PMs into builders. Since then, Meta has become a smaller, flatter company. We get into how that version of Meta, with fewer PMs and layers, pulled in record revenues with its smallest team in years. – Key topics: • A smaller, flatter Meta building more, not less • Why "the glory days of being a PM in big tech are still ahead of us" • Pointing AI agents at Meta's old codebase to scaffold a new app in weeks • The new IC9 and IC10 ladder • Why design and data science aren't shrinking • Why Jagjit reversed his opinion on PMs shipping production code • Explaining AI evals using bath towels • The interview question that screens for "AI PM" judgment • Why he isn't worried about the industry's next hiring swing – Timestamps: 00:00 Introduction 02:02 A return visit to see how Meta's AI predictions landed 03:28 Facebook's super-app problem 07:58 Pointing AI agents at Meta's old codebase to scaffold a new app in weeks 11:15 Where Bolt, Lovable, and Replit still can't compete 13:59 Why the new apps aren't cannibalizing Facebook 18:01 Why PMs get the first mile and designers get the last 23:07 Why Jagjit reversed his opinion on PMs shipping production code 24:37 How homegrown AI habits became company-wide baseline tools 29:06 Why "the glory days of being a PM in big tech are still ahead of us" 31:38 "Facebook is like the world's largest Jenga tower" 37:52 The test for converting a manager back into an IC 39:48 The new IC9 and IC10 ladder 42:35 Explaining AI evals using bath towels 46:26 How to coach someone into becoming an "AI PM" 49:37 Should you do a tour of duty at big tech? 53:44 Why Jagjit isn't worried about the industry's next hiring swing – Brought to you by: • Jira—Do the right work with Jira – Referenced: • Bolt • Facebook • Facebook Creator Studio • Forum, a Facebook app • Google • How Meta Is Reinventing Product Management • Instagram • Instagram Edits • Lovable • Messenger • Meta • Meta's Rotational Programs • Replit • Seller, a Facebook app • Threads • TikTok • WhatsApp • YouTube – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Jagjit: • 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 [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, Saswat Panigrahi, Waymo's CPO, joins me for the third conversation in the "Inside PM" series. Saswat joined Waymo in 2016, back when it was still Google's self-driving car project and the entire product team was fewer than five people, and has spent all ten years since on the same product. In this episode, we discuss how his product org had to invent its own way of measuring good when there was no dashboard to check, why he hires and promotes for competence, courage, and compassion, and what it takes to be an executive builder at Waymo. – Key topics: • Cutting severe injuries "sixteen-fold" • Why measuring good driving became its own product, staffed by dedicated eval PMs • Why specifying what good looks like is AI's hardest problem • Injecting rain and fog into simulated scenes instead of waiting a decade for the real thing • The living room pitch to Waymo's first driverless riders • Avoiding "Brownian motion": channeling vision into tracks a team can actually execute • Spotting curiosity and grit in candidates in the age of AI • Training to the point of failure – Timestamps: 00:00 Introduction 03:25 Joining Google's self-driving car project before it was Waymo 07:15 Why "feeling the pain" of failures builds real product leadership 08:56 Motivating a team a decade away from a real product 14:38 Was there ever a moment you thought this wouldn't work 16:15 Why measuring "good" driving became its own product, staffed by dedicated eval PMs 18:55 The living room pitch to Waymo's first driverless riders 21:11 Confronting the 40,000 deaths US roads accept every year 23:46 Cutting severe injuries "sixteen-fold" 27:59 Training to the point of failure 33:27 Spotting curiosity and grit in candidates in the age of AI 37:14 Integrity, and sleeping at night over what you approved 41:02 A tree of metrics, not a union list of 37 dashboards 47:14 Competence, courage, and compassion: what builds followership 53:53 What AI has democratized for product discovery and research 57:41 Why specifying "what good looks like" is AI's hardest problem – Brought to you by: • Firecrawl—the web data API for AI agents. Use code THESKIP for 10K free credits • Jira—Do the right work with Jira – Referenced: • AMD • Edwin Markham's poem on preparedness • Google X • Inside PM at Meta • Inside PM at Stripe • MMLU • NASA • Piccadilly Circus • Transformers • Waymo – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Saswat: • Twitter/X • 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 [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

This is the next episode in a series on what product management becomes when the AI hype meets real constraints. I sat down with three CPOs living about a year ahead of the rest of us: Sharmeen Chapp, Midjourney's first-ever product hire; Jiaona Zhang (JZ), CPO at Laurel; and Henrik Berggren, who runs product and design at Mutiny. Their teams are tiny on purpose, yet these are companies with years of history, paying customers, and enterprise contracts—not the frictionless blank slates that "AI-native" suggests. We get into who should actually be building, how customer signal should move through a company, and how each of them installed an AI-first operating system without tipping into theater. – Key topics: • What never changes in PM • Laurel's "captain" model: everyone is a builder • Zoning the codebase like a garden so everyone can build safely • Making the whole company understand the customer • The AI Operations team: pairing hackers with leaders • Treating the AI transformation as a product, with employees as the users • Moving at "Cheetah speed": sprint when the tools jump, then rest • Current PMs are managing a fleet, not an empire • Why the strongest leaders are going hands-on now – Timestamps: (00:00) Introduction (03:30) Meet the three CPOs: Midjourney, Laurel, Mutiny (08:45) Laurel's "captain" model: everyone is a builder (13:03) Zoning the codebase like a garden (17:19) Governing change when anyone can ship to production (18:23) Sharmeen at Midjourney: installing product judgment (21:53) Henrik on finding the line by stepping over it (24:57) A Slack channel that pings on every meaningful action (26:59) Running AI in public so skeptics convert (29:29) The AI Operations team: pairing hackers with leaders (32:15) Incentives, public systems, and evergreen context (36:46) Managing context overload with distributed PM (39:45) A user interview to shareable clips in 45 minutes (45:16) First-party vs. third-party: what to build, what to buy (47:34) The token-maximization "blip" and raising the floor (49:31) Managing a fleet, not an empire (53:40) "Cheetah speed": sprint when the tools jump, then rest (56:37) Why the strongest leaders are going hands-on now (57:29) Does the pendulum swing back to old-school PM? (59:48) What never changes: business, customer, orchestration – Brought to you by: • Firecrawl—Power AI agents with clean web data • Use code THESKIP for 10K free credits – Referenced: • Anthropic • Cursor • Devin • Dropbox • Dust • GitHub • Google Drive • Grain • Granola • Laurel • Meta • Midjourney • Mutiny • Notion • Procter & Gamble • Slack • Stripe • Twitch – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Sharmeen: • Twitter/X • LinkedIn – Where to find JZ: • Twitter/X • LinkedIn – Where to find Henrik: • Twitter/X • 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 [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

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 Introduction 03:40 What Kevin owns across Stripe's merchant experiences 05:24 Stop asking which role dies, focus on the outcomes 08:05 The three PM archetypes, and why zero-to-one changed most 10:50 Kill your darlings: keeping the blast radius small 14:30 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 fear 22:50 Are wikis and knowledge artifacts back? 28:42 How Stripe incentivizes sharing: carrots over sticks 31:35 The pet peeve: 10 prototypes, zero users 35:20 Onboarding as a product: the first 100 days 38:16 Writing as "clarity at scale," and why LLMs still can't do it 45:35 The "piano scales" for a PM: forming an opinion 48:37 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 [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

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 approach Timestamps: (00:00) Introduction (00:39) The 100-day shift: builder execs and $10M offers (04:04) Case 1, Angie: two safe offers and an AI-bubble fear(05:04) Optimizing to be elite, or just to be prudent? (06:58) Why a failed hot startup can leave you better off (10:58) Thinking about what your next role sets up, not just the salary (15:40) Case 2, Gary: Series A vs. Fortune 20 (16:36) Working backward from the PE operating-partner dream (18:58) The biggest job at the most current company, not the best (22:40) How to tell if a company is actually "current" (25:26) Case 3, Monica: elite, comfortable, and chasing joy (26:57) One more operating role, then founding (29:33) Choosing mercenary over missionary (35:26) Would the right company help her find a co-founder (37:18) 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 [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

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 it Timestamps: 00:00 Introduction 05:47 Why the biggest change is pace 07:29 From detailed PRDs to a paragraph, a prototype, and an eval set 09:32 Why the management "compression algorithm" is dead 10:37 Visibility is high, but synthesis is scarce 14:45 "Finding a scissor" when you don't have fancy tools 16:10 A morning brief that flags the decisions only you can make 22:37 When the agent quietly drops your source links 25:53 The one job AI can't take: influencing other humans 30:18 Getting an analyst's answer in five minutes, not 24 hours 33:33 Three ways AI changed the products, not just the process 37:25 Why letting AI write code made site incidents spike 40:39 The no-meeting week and the birth of "AI captains" 44:55 The world's largest Jenga game: why institutional knowledge wins 48:41 Why economics and physics PhDs are "out-PMing" engineers 52:14 Ideas and agency before tools 56:19 "AI lowers the floor and raises the ceiling" 58:40 Closing advice: once you taste it, you can't go back Brought to you by: • Glean—Work AI that works • Framer—Design and build your website effortlessly with Framer Agents Referenced: • 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 • Zoom Where to find Nikhyl: • Twitter/X • LinkedIn Where to find Jagjit: • 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 [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 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 level Referenced: • Anthropic • ChatGPT • Claude • Copilot • Facebook • Google • Meta 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] Brought to you by: • Glean—Work AI that works • Guru—Trusted knowledge for every AI tool and team 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 Timestamps: 00:00 Introduction 03:32 Finding the question behind the question 06:00 The director with three short stints weighing their next option 07:17 Breaking out of the "layoff merry-go-round" 14:37 Why founding should only stay on the table if you're truly obsessed 17:18 The manager whose top performer turned adversarial 18:41 How the sponsor-to-manager collision actually happens 24:48 "Every superpower comes with a shadow" 25:30 Why some management relationships reach a graduation 35:02 The exec fielding multiple offers and the question underneath 41:27 How to know you've earned the right to seek balance 46:50 Remove "great manager" from your job search checklist 51:17 The pretzel framework: find the culture where you bend least 57:20 The new manager whose first direct report is more experienced than them 58:25 Why being "safe" matters more than matching your report's credentials 1:02:40 "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 theskip.substack.com

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 time Referenced: • 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.com Brought 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/skip Where to find Nikhyl • Twitter/X • LinkedIn Where to find Dana • LinkedIn Where to find Briana • LinkedIn Where to find Pei-Chin • LinkedIn Join The Skip • Skip Coach • Skip Community Find The Skip • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps: 00:00 Introduction 04:08 Welcome, and why this is the second job-search postmortem 05:50 Meet Dana, Briana, and Pei-Chin 06:15 What the "smiling exhaustion" state is 09:58 Three career transitions, three different triggers 15:26 Has founding become a must-have on the modern career path? 17:09 Why "AI company" doesn't need to be a hard filter 21:43 The new founding math: Three-month traction windows and "everyone codes" 26:16 How AI agents flipped onboarding from headwind to tailwind 31:33 How to navigate the decline of remote-friendly roles 36:27 Setting hard family boundaries in the 996-company era 40:47 How proactive do senior leaders need to be to build their role pipeline? 43:10 Standing out to recruiters when your CV lacks traditional experience 47:43 Discovering Claude Code: "I felt like a sorcerer" 53:21 Why structured AI learning isn't necessary 57:21 When your resume doesn't fit the pattern, teach the interviewer 58:48 Closing wisdom: hold your identity loosely 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

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 skills 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 Timestamps: 00:00 Introduction 00:40 You're not behind, you're right on time 03:23 The senior PM who stepped backwards and lost her identity 04:36 Why "you're in mourning" is the first thing to say out loud 08:38 Builder vs. capital-M Manager: who the industry is actually hiring 12:28 The IC5 at a FAANG, the immigration clock, and infrastructure work 13:31 Why last year's "suck it up" advice stopped working 18:30 If you have builder instincts, you need to make sure people know about it 20:02 Navigating layoff season: Who should be worried and who should relax 23:02 The ageism reframe: Why a beginner's mentality beats pedigree 25:47 The 50-year-old veteran caught between coaching and "a real job" 27:29 Why coaching isn't a durable career in the LLM era 28:51 The "double jump" job-search strategy: get back in motion first 33:12 The mid-career operator who's convinced he's hit a dead end 35:30 Why being "non-technical" is no longer a blocker in 2026 36:09 How to reframe breadth of experience to form a power combination 39:03 "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

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 performer Where to find Nikhyl • Twitter/X • LinkedIn Where to find McKenzie • LinkedIn Where to find Sam • LinkedIn Where to find Sarah • LinkedIn Join The Skip • Skip Coach • Skip Community Find The Skip • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps 00:48 Introduction 04:12 Meet our guests from EvenUp, Rippling, and Netflix 09:06 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 ability 16:16 Past experience vs. scenario questions—where the balance is shifting 19:52 Does pedigree still matter to hiring managers? 23:10 Why trajectory is an underrated signal to index on 26:43 Why the LinkedIn DM isn't dead 29:31 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 thinking 39:09 Rippling's product discussion and panel case study process 43:52 Unpacking red flags in case study presentations 45:43 The collaboration test: curiosity vs. defensiveness under pressure 47:56 How to get noticed — are website applications even worth it? 50:56 Where EvenUp proactively sources candidates 53:00 Closing advice for mid-career PMs navigating today's job market 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

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 them References: • Claude: https://www.claude.ai • Floodgate: https://www.floodgate.com • LinkedIn: https://www.linkedin.com • Meta: https://www.meta.com • OpenAI: https://www.openai.com Brought 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/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 Introduction 03:18 Why organizational politics are so top of mind 04:59 “Everything’s changing, and no one’s telling me anything” 06:35 The two common reasons behind radio silence 12:41 Tough conversations shouldn’t be your first conversations 15:05 Why confrontation isn’t always the answer 17:35 Avoid putting your manager in a defensive position 22:12 Why role tenure is more malleable than you think 26:18 When a company reorg shifts you into a new role 29:55 How modern is your skillset? 33:57 How to identify whether burnout is worth it 40:03 Is the cost of your ambition future regret? 45:12 How to deal with an underperforming manager 55:23 Leaving a dysfunctional team for a new one 59:14 Drive impact first, talk long-term goals second 1:02:06 Why managers respond positively to specific goals 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

Most of the conversation about rebuilding product management comes from two ends of the spectrum: AI-first startups with 30 people and no real installed base, or big tech with thousands of PMs and decades of process. This episode is about the third category: companies that went public in the last few years, have real customers and revenue to protect, and are now trying to move like startups again. The CPOs of Hims & Hers, Rubrik, and Figma joined me to discuss what that actually looks like. Several of their findings directly contradict the advice you'd get from either end of the spectrum. Key topics • Why going public doesn't mean replacing your PM team with "business people" • Why AI makes PM workload explode, not shrink • What happens when engineering is no longer the bottleneck • The skill Figma values most at scale (and why speed is the wrong thing to optimize for) • Whether the IPO date is a real line in the sand—and why Yuhki and Anneka land in different places • Why AI adoption at post-IPO companies requires the CPO to go first • How Anneka wrote her team's Claude Code onboarding guide, opened the GitHub repos, and built a triage agent between meetings • Why Dheerja joined Hims & Hers as the "AI Queen" • Dheerja’s three-part AI framework she’s executing on • Why Yuhki hired AI veterans first—then immediately hired people with no AI background at all • The case against take-homes (and Anneka's idea for what should replace them) • What a blank canvas reveals about a PM candidate that no case study or behavioral question can • Why every PM is about to become a manager of agents • How to talk to your team when the stock is down and you haven't announced anything new • Why Figma deprecated annual planning—and what Yuhki thinks will become core PM work within a year Where to find Nikhyl • Twitter/X • LinkedIn Where to find Anneka • LinkedIn Where to find Dheerja • LinkedIn Where to find Yuhki • LinkedIn Join The Skip • Skip Coach • Skip Community Find The Skip • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps (00:00) Anneka on leading from the top: visibly & vulnerably (00:45) Intro: three CPOs, one inflection point (05:53) How PM accountability shifts from startup to post-IPO (07:24) The GM model: when PMs own P&L, not just product metrics (10:54) Hiring systems thinkers over feature builders (15:08) Where AI is actually moving the needle in enterprise B2B (20:37) The three components of AI transformation (24:13) How going public changes perception management at Figma (27:00) Navigating stock drops and keeping teams focused (30:30) Creating space for AI learning when the team is already maxed (35:12) 3 steps to seeding AI teams (40:03) How everyone is becoming a manager of agents (44:34) Yuhki on resourcefulness and the blank canvas take-home (47:40) Dheerja: go an hour deep on one real decision in the interview (50:56) Why live pair Claude Code sessions is the future of PM interviews (53:13) Predictions for 2026 and beyond (55:34) Why it’s the best time in history to be a PM 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