The Skip Podcast

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continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways.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