The Skip Podcast

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

Most job search advice comes from people still in the thick of it—anxious, second-guessing, pattern-matching off too little data. This episode is different. We sat down with three product leaders who recently landed roles at Netflix, OpenAI, and Abridge, and did a full postmortem. What they shared upends a lot of conventional wisdom: the spray-and-pray pipeline doesn't work, your AI credentials matter less than you think, and the relationships that land jobs are often years in the making.

Key topics
• Why you need curiosity, not experience
• The "AI hungry" mindset: searching for environments that match your learning goals, not just your resume
• Why the best job search intelligence comes from people who just landed, not people still looking
• Why prototypes are now table stakes in take-homes
• How Janie built a shortlist of 5–10 companies in a week of 50–60 conversations
• Why Ben's Netflix role traces back to a cold application seven years ago
• What OpenAI's interview process actually looks like—and why it's less about the past than you expect
• Why most AI-native jobs aren't posted, and how to land them
• How to use investor attention as a proxy for company quality
• Why Ben's early interview mistake (not enough AI mindset) became the fuel for his take-home

Brought to you by
• Framer—Build websites with enterprise needs at startup speeds: https://framer.link/dFacxBQ
• Dust—The operating system for AI agents: https://dust.tt/skip

Where to find Nikhyl
• Twitter/X
• LinkedIn

Where to find Ben
• LinkedIn

Where to find Janie
• LinkedIn

Where to find Julia
• LinkedIn

Join The Skip
• Skip Coach
• Skip Community

Find The Skip
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts

Timestamps
(00:00) How to prove your AI credentials
(04:42) Introducing the three product leaders
(06:00) Ben Dreier: from DoorDash to Netflix, the "AI hungry" move
(08:18) Julia Roberts: nine years at Pinterest, six months off, then OpenAI
(12:46) Janie Lee: going all-in on AI native at Abridge
(15:26) How to build a shortlist: 50–60 conversations in a week
(18:10) Ben's process: VC signals and insider conversations over job boards
(21:45) Cold outreach that actually works
(23:51) Ben: how curiosity, not networking, built his network
(25:14) Julia's different path: cold applies, inbound, and exec recruiters
(27:06) What exec recruiters are actually useful for
(30:30) Ben's Netflix backstory — tracing back to a cold apply seven years ago
(34:06) Staying connected with recruiters, coworkers, and people who said no
(41:10) What the OpenAI interview process actually looks like
(44:55) Authentic storytelling
(46:40) The Netflix take-home: how mid-process feedback became a turning point
(51:40) Janie: how to ace take-homes by using AI
(57:52) Julia’s final takeaway: know what you want before you search
(59:03) Ben’s final takeaway: follow the fun and genuine curiosity
(59:56) Janie’s final takeaway: high agency, high effort, put yourself in their shoes

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