The Skip Podcast

<p>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continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways.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.</p><p></p><p><strong>Key topics:</strong></p><p>• 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</p><p>• The new founding math: fast, fun, and skill-additive, with a much lower downside than it used to be</p><p>• How to navigate the job search when you don’t live in San Francisco—and remote jobs are dwindling</p><p>• Why structured AI learning is the wrong move, and what to build instead, so your fluency is hard to fake</p><p>• How to signal hard boundaries to a new boss, and differentiate between real respect and performative virtue-signalling</p><p>• Why holding your professional identity loosely matters when the role of senior leader is getting reformatted in real time</p><p></p><p><strong>Referenced:</strong></p><p>• Airbnb: <a target="_blank" href="https://www.airbnb.com/">https://www.airbnb.com/</a></p><p>• Atlassian: <a target="_blank" href="https://www.atlassian.com">https://www.atlassian.com</a></p><p>• Claude Code: <a target="_blank" href="https://claude.com/product/claude-code">https://claude.com/product/claude-code</a></p><p>• Harvey: <a target="_blank" href="https://www.harvey.ai">https://www.harvey.ai</a></p><p>• Loom: <a target="_blank" href="https://www.loom.com">https://www.loom.com</a></p><p>• Modern Animal: <a target="_blank" href="https://themodernanimal.com">https://themodernanimal.com</a></p><p></p><p><strong>Brought to you by:</strong></p><p>• Guru—Trusted knowledge for every AI tool and team: <a target="_blank" href="https://www.getguru.com/?utm_source=the-skip&#38;utm_medium=podcast&#38;utm_campaign=skip-promo">https://www.getguru.com/?utm_source=the-skip&utm_medium=podcast&utm_campaign=skip-promo</a></p><p>• <a target="_blank" href="http://Customer.io">Customer.io</a>—The customer engagement platform for human messaging: <a target="_blank" href="http://customer.io/skip">http://customer.io/skip</a></p><p></p><p><strong>Where to find Nikhyl</strong></p><p>• <a target="_blank" href="https://x.com/nikhyl">Twitter/X</a></p><p>• <a target="_blank" href="https://www.linkedin.com/in/nikhyl/">LinkedIn</a></p><p></p><p><strong>Where to find Dana</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/danabressler/">LinkedIn</a></p><p></p><p><strong>Where to find Briana</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/briana-ings/">LinkedIn</a></p><p></p><p><strong>Where to find Pei-Chin</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/peichin/">LinkedIn</a></p><p></p><p><strong>Join The Skip</strong></p><p>• <a target="_blank" href="https://skip.coach/">Skip Coach</a></p><p>• <a target="_blank" href="https://skip.community/">Skip Community</a></p><p></p><p><strong>Find The Skip</strong></p><p>• <a target="_blank" href="https://www.skip.community/">Website</a></p><p>• <a target="_blank" href="https://theskip.substack.com/">Substack</a></p><p>• <a target="_blank" href="https://www.youtube.com/@theskippodcast">YouTube</a></p><p>• <a target="_blank" href="https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ">Spotify</a></p><p>• <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202">Apple Podcasts</a></p><p></p><p><strong>Timestamps:</strong></p><p>00:00 Introduction</p><p>04:08 Welcome, and why this is the second job-search postmortem</p><p>05:50 Meet Dana, Briana, and Pei-Chin</p><p>06:15 What the "smiling exhaustion" state is</p><p>09:58 Three career transitions, three different triggers</p><p>15:26 Has founding become a must-have on the modern career path?</p><p>17:09 Why "AI company" doesn't need to be a hard filter</p><p>21:43 The new founding math: Three-month traction windows and "everyone codes"</p><p>26:16 How AI agents flipped onboarding from headwind to tailwind</p><p>31:33 How to navigate the decline of remote-friendly roles</p><p>36:27 Setting hard family boundaries in the 996-company era</p><p>40:47 How proactive do senior leaders need to be to build their role pipeline?</p><p>43:10 Standing out to recruiters when your CV lacks traditional experience</p><p>47:43 Discovering Claude Code: "I felt like a sorcerer"</p><p>53:21 Why structured AI learning isn't necessary</p><p>57:21 When your resume doesn't fit the pattern, teach the interviewer</p><p>58:48 Closing wisdom: hold your identity loosely</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://theskip.substack.com?utm_medium=podcast&#38;utm_campaign=CTA_1">theskip.substack.com</a>

<p>If you're in a career transition right now and wondering whether you did something wrong, you didn't. Every question coming into <a target="_blank" href="http://Nikhyl.AI">Nikhyl.AI</a> 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.</p><p>Key topics:</p><p>• Why the first stage of any transition is mourning, and why most people get stuck there</p><p>• The builder vs. manager divide: why "capital-P Product Managers" are thriving and "capital-M product Managers" are not</p><p>• Why proving to yourself and others that you’re a builder is the currency that keeps you alive in the next round of layoffs</p><p>• The uncanny valley of mid-to-late-career PMs and how you can climb out of it</p><p>• Why coaching, consulting, and advisory roles are shrinking careers in a world of rapidly-improving LLMs</p><p>• The “double-jump” job search strategy and why you should stop optimizing for the 10-year role</p><p>• How you can turn a non-PM background into a superpower with AI and product skills</p><p></p><p><strong>Where to find Nikhyl</strong></p><p><a target="_blank" href="https://x.com/nikhyl">Twitter/X</a></p><p><a target="_blank" href="https://www.linkedin.com/in/nikhyl/">LinkedIn</a></p><p></p><p><strong>Where to find Carly</strong></p><p><a target="_blank" href="https://www.linkedin.com/in/carlymalatskey/">LinkedIn</a></p><p></p><p><strong>Join The Skip</strong></p><p><a target="_blank" href="https://skip.coach/">Skip Coach</a></p><p><a target="_blank" href="https://skip.community/">Skip Community</a></p><p></p><p><strong>Find The Skip</strong></p><p><a target="_blank" href="https://www.skip.community/">Website</a></p><p><a target="_blank" href="https://theskip.substack.com/">Substack</a></p><p><a target="_blank" href="https://www.youtube.com/@theskippodcast">YouTube</a></p><p><a target="_blank" href="https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ">Spotify</a></p><p><a target="_blank" href="https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202">Apple Podcasts</a></p><p></p><p><strong>Timestamps:</strong></p><p>00:00 Introduction</p><p>00:40 You're not behind, you're right on time</p><p>03:23 The senior PM who stepped backwards and lost her identity</p><p>04:36 Why "you're in mourning" is the first thing to say out loud</p><p>08:38 Builder vs. capital-M Manager: who the industry is actually hiring</p><p>12:28 The IC5 at a FAANG, the immigration clock, and infrastructure work</p><p>13:31 Why last year's "suck it up" advice stopped working</p><p>18:30 If you have builder instincts, you need to make sure people know about it</p><p>20:02 Navigating layoff season: Who should be worried and who should relax</p><p>23:02 The ageism reframe: Why a beginner's mentality beats pedigree</p><p>25:47 The 50-year-old veteran caught between coaching and "a real job"</p><p>27:29 Why coaching isn't a durable career in the LLM era</p><p>28:51 The "double jump" job-search strategy: get back in motion first</p><p>33:12 The mid-career operator who's convinced he's hit a dead end</p><p>35:30 Why being "non-technical" is no longer a blocker in 2026</p><p>36:09 How to reframe breadth of experience to form a power combination</p><p>39:03 "You didn't defer reinvention. You waited until now."</p><p>42:27 Embracing reinvention: First, mourn — then get back into motion</p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://theskip.substack.com?utm_medium=podcast&#38;utm_campaign=CTA_1">theskip.substack.com</a>

<p>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.</p><p>Key topics:</p><p>• The new PM: Why companies are looking for candidates who “push the limits of what’s possible”</p><p>• The shift from behavioral to scenario-based questions</p><p>• Does pedigree still matter? Why trajectory is the new alternative signal for recruiters</p><p>• The three things that now separate a great take-home case study submission from a generic one</p><p>• Why case study presentations are still valuable - and help demonstrate core PM skills</p><p>• Whether website applications actually get looked at and why referrals are more binary than most people think</p><p>• How to signal drive and a frontier-pushing mindset when everyone claims to be a high performer</p><p><strong>Where to find Nikhyl</strong></p><p>• <a target="_blank" href="https://x.com/nikhyl">Twitter/X</a></p><p>• <a target="_blank" href="https://www.linkedin.com/in/nikhyl/">LinkedIn</a></p><p><strong>Where to find McKenzie</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/mckenzielock/">LinkedIn</a></p><p><strong>Where to find Sam</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/samstone/">LinkedIn</a></p><p><strong>Where to find Sarah</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/sarahkoo/">LinkedIn</a></p><p><strong>Join The Skip</strong></p><p>• <a target="_blank" href="https://skip.coach/">Skip Coach</a></p><p>• <a target="_blank" href="https://skip.community/">Skip Community</a></p><p><strong>Find The Skip</strong></p><p>• <a target="_blank" href="https://www.skip.community/">Website</a></p><p>• <a target="_blank" href="https://theskip.substack.com/">Substack</a></p><p>• <a target="_blank" href="https://www.youtube.com/@theskippodcast">YouTube</a></p><p>• <a target="_blank" href="https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ">Spotify</a></p><p>• <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202">Apple Podcasts</a></p><p><strong>Timestamps</strong></p><p>00:48 Introduction </p><p>04:12 Meet our guests from EvenUp, Rippling, and Netflix</p><p>09:06 How has the hiring process changed since COVID?</p><p>11:17 Is AI fluency explicitly tested in interviews?</p><p>12:42 Why quality and speed are favored over prioritization ability</p><p>16:16 Past experience vs. scenario questions—where the balance is shifting</p><p>19:52 Does pedigree still matter to hiring managers?</p><p>23:10 Why trajectory is an underrated signal to index on</p><p>26:43 Why the LinkedIn DM isn't dead</p><p>29:31 Does the take-home case study still hold value in the AI era?</p><p>33:21 Using case studies to screen for brevity, agency, and strategic thinking</p><p>39:09 Rippling's product discussion and panel case study process</p><p>43:52 Unpacking red flags in case study presentations</p><p>45:43 The collaboration test: curiosity vs. defensiveness under pressure</p><p>47:56 How to get noticed — are website applications even worth it?</p><p>50:56 Where EvenUp proactively sources candidates</p><p>53:00 Closing advice for mid-career PMs navigating today's job market</p><p>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 <a target="_blank" href="http://skip.coach">skip.coach</a>. 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 <a target="_blank" href="mailto:[email protected]">[email protected]</a></p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://theskip.substack.com?utm_medium=podcast&#38;utm_campaign=CTA_1">theskip.substack.com</a>

<p>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.</p><p><strong>Key topics</strong></p><p>• What to do when leadership goes dark, and you can't tell if a reorg is coming</p><p>• The stay-vs-go framework: when brand matters, when comp overrides it, and why short tenures are more common than most people think</p><p>• The one question that puts your manager in an impossible position</p><p>• How to navigate an underperforming direct manager</p><p>• Why acting before a restructure is announced gives you a head start</p><p>• How to build the relationships you'll need on a rainy day before you actually need them</p><p>• What happens when VP sponsorship and calibration approval still aren't enough to get promoted</p><p>• How to start fresh on a new team when you're leaving a dysfunctional one behind</p><p>• The five-point playbook for navigating office politics without getting swept into them</p><p></p><p><strong>References:</strong></p><p>• Claude: <a target="_blank" href="https://www.claude.ai">https://www.claude.ai</a></p><p>• Floodgate: <a target="_blank" href="https://www.floodgate.com">https://www.floodgate.com</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com">https://www.linkedin.com</a></p><p>• Meta: <a target="_blank" href="https://www.meta.com">https://www.meta.com</a></p><p>• OpenAI: <a target="_blank" href="https://www.openai.com">https://www.openai.com</a></p><p></p><p><strong>Brought to you by</strong></p><p>• Framer—Build websites with enterprise needs at startup speeds: <a target="_blank" href="https://framer.link/dFacxBQ">https://framer.link/dFacxBQ</a></p><p>• <a target="_blank" href="http://Customer.io">Customer.io</a>—The customer engagement platform for human messaging: <a target="_blank" href="http://customer.io/skip">http://customer.io/skip</a></p><p></p><p><strong>Where to find Nikhyl</strong></p><p>• <a target="_blank" href="https://x.com/nikhyl">Twitter/X</a></p><p>• <a target="_blank" href="https://www.linkedin.com/in/nikhyl/">LinkedIn</a></p><p><strong>Where to find Carly:</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/carlymalatskey">LinkedIn</a></p><p>• <a target="_blank" href="https://www.sheleadspod.com/">She Leads Podcast</a></p><p>• <a target="_blank" href="https://x.com/carlymalatskey">Twitter/X</a></p><p></p><p><strong>Join The Skip</strong></p><p>• <a target="_blank" href="https://skip.coach/">Skip Coach</a></p><p>• <a target="_blank" href="https://skip.community/">Skip Community</a></p><p></p><p><strong>Find The Skip</strong></p><p>• <a target="_blank" href="https://www.skip.community/">Website</a></p><p>• <a target="_blank" href="https://theskip.substack.com/">Substack</a></p><p>• <a target="_blank" href="https://www.youtube.com/@theskippodcast">YouTube</a></p><p>• <a target="_blank" href="https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ">Spotify</a></p><p>• <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202">Apple Podcasts</a></p><p></p><p><strong>Timestamps:</strong></p><p>00:00 Introduction</p><p>03:18 Why organizational politics are so top of mind</p><p>04:59 “Everything’s changing, and no one’s telling me anything”</p><p>06:35 The two common reasons behind radio silence</p><p>12:41 Tough conversations shouldn’t be your first conversations</p><p>15:05 Why confrontation isn’t always the answer</p><p>17:35 Avoid putting your manager in a defensive position</p><p>22:12 Why role tenure is more malleable than you think</p><p>26:18 When a company reorg shifts you into a new role</p><p>29:55 How modern is your skillset?</p><p>33:57 How to identify whether burnout is worth it</p><p>40:03 Is the cost of your ambition future regret?</p><p>45:12 How to deal with an underperforming manager</p><p>55:23 Leaving a dysfunctional team for a new one</p><p>59:14 Drive impact first, talk long-term goals second</p><p>1:02:06 Why managers respond positively to specific goals</p><p>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 <a target="_blank" href="http://skip.coach">skip.coach</a>. 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 <a target="_blank" href="mailto:[email protected]">[email protected]</a></p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://theskip.substack.com?utm_medium=podcast&#38;utm_campaign=CTA_1">theskip.substack.com</a>

<p>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.</p><p>Key topics</p><p>• Why going public doesn't mean replacing your PM team with "business people"</p><p>• Why AI makes PM workload explode, not shrink</p><p>• What happens when engineering is no longer the bottleneck</p><p>• The skill Figma values most at scale (and why speed is the wrong thing to optimize for)</p><p>• Whether the IPO date is a real line in the sand—and why Yuhki and Anneka land in different places</p><p>• Why AI adoption at post-IPO companies requires the CPO to go first</p><p>• How Anneka wrote her team's Claude Code onboarding guide, opened the GitHub repos, and built a triage agent between meetings</p><p>• Why Dheerja joined Hims & Hers as the "AI Queen"</p><p>• Dheerja’s three-part AI framework she’s executing on</p><p>• Why Yuhki hired AI veterans first—then immediately hired people with no AI background at all</p><p>• The case against take-homes (and Anneka's idea for what should replace them)</p><p>• What a blank canvas reveals about a PM candidate that no case study or behavioral question can</p><p>• Why every PM is about to become a manager of agents</p><p>• How to talk to your team when the stock is down and you haven't announced anything new</p><p>• Why Figma deprecated annual planning—and what Yuhki thinks will become core PM work within a year</p><p><strong>Where to find Nikhyl</strong></p><p>• <a target="_blank" href="https://x.com/nikhyl">Twitter/X</a></p><p>• <a target="_blank" href="https://www.linkedin.com/in/nikhyl/">LinkedIn</a></p><p><strong>Where to find Anneka</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/annekagupta/">LinkedIn</a></p><p><strong>Where to find Dheerja</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/dheerja/">LinkedIn</a></p><p><strong>Where to find Yuhki</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/yuhki/">LinkedIn</a></p><p><strong>Join The Skip</strong></p><p>• <a target="_blank" href="https://skip.coach/">Skip Coach</a></p><p>• <a target="_blank" href="https://skip.community/">Skip Community</a></p><p><strong>Find The Skip</strong></p><p>• <a target="_blank" href="https://www.skip.community/">Website</a></p><p>• <a target="_blank" href="https://theskip.substack.com/">Substack</a></p><p>• <a target="_blank" href="https://www.youtube.com/@theskippodcast">YouTube</a></p><p>• <a target="_blank" href="https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ">Spotify</a></p><p>• <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202">Apple Podcasts</a></p><p><strong>Timestamps</strong></p><p>(00:00) Anneka on leading from the top: visibly & vulnerably</p><p>(00:45) Intro: three CPOs, one inflection point</p><p>(05:53) How PM accountability shifts from startup to post-IPO</p><p>(07:24) The GM model: when PMs own P&L, not just product metrics</p><p>(10:54) Hiring systems thinkers over feature builders</p><p>(15:08) Where AI is actually moving the needle in enterprise B2B</p><p>(20:37) The three components of AI transformation</p><p>(24:13) How going public changes perception management at Figma</p><p>(27:00) Navigating stock drops and keeping teams focused</p><p>(30:30) Creating space for AI learning when the team is already maxed</p><p>(35:12) 3 steps to seeding AI teams</p><p>(40:03) How everyone is becoming a manager of agents</p><p>(44:34) Yuhki on resourcefulness and the blank canvas take-home</p><p>(47:40) Dheerja: go an hour deep on one real decision in the interview</p><p>(50:56) Why live pair Claude Code sessions is the future of PM interviews</p><p>(53:13) Predictions for 2026 and beyond</p><p>(55:34) Why it’s the best time in history to be a PM</p><p>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 <a target="_blank" href="http://skip.coach">skip.coach</a>. 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 <a target="_blank" href="mailto:[email protected]">[email protected]</a></p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://theskip.substack.com?utm_medium=podcast&#38;utm_campaign=CTA_1">theskip.substack.com</a>