The Skip Podcast
- Épisodes
- 62
- Parution
- toutes les deux semaines
- Dernier épisode
- 12 Nov 2026
À propos du podcast
The Skip podcast helps tech professionals get ahead in their career. It's hosted by Nikhyl Singhal, a three-time founder, CPO, and product executive at Meta and Google. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. He now runs Skip Coach, a career service powered by the world's top CPO community, and has coached hundreds of product leaders through career decisions, management challenges, and transitions. Subscribe for career insights distilled from real coaching conversations.
Épisodes 62
How to Stay Current, Get Hired, and Last in AI
In this episode, I sit down in person with three of my closest friends in The Skip Community, each of whom took on an AI role recently: Dana Ingraham, who runs core product at Harvey after seven years at …
Notes de l’épisode
In this episode, I sit down in person with three of my closest friends in The Skip Community, each of whom took on an AI role recently: Dana Ingraham, who runs core product at Harvey after seven years at Airbnb, Hemal Shah, who moved from OpenAI to Google Cloud, and Jiaona "JZ" Zhang, CPO of Laurel and formerly of Webflow. We get into the common product career advice they push back on, from needing to be “AI-pilled” to land an AI job, to following everything to stay current, to judging a company by its valuation, and what they do instead. We also talk about how they manage all-consuming jobs with young families at home, and why JZ says AI "literally makes us able to do all the things."
–
Key topics:
• Why Dana disagrees that you need to be "AI-pilled" to get an AI job, and what she hires for instead
• Hemal's three skills of a great PM today: historian, technologist, and anthropologist
• Why curiosity and adapting to change as the traits that matter even more now
• Staying current through "people curation" instead of consuming everything
• Choosing a company by its data, distribution, people, and willingness to change
• Why JZ recommends forward-deployed and AI operations roles over waiting for a PM title
• Ruthless prioritization: "What is one thing I would regret not doing with my time right now?"
• Why joy, not time management, prevents burnout
–
Timestamps:
00:00 Introduction
04:38 Meet the three leaders who each took on a new AI role
05:22 What they built at home with AI, from college applications to kids' apps
11:33 How do they find the time?
14:24 Why JZ says yes to teaching at Yale and no to almost everything else
16:33 Hemal on why you can't have it all
17:58 Why Dana left Airbnb after seven years for Harvey
20:12 Ruthless prioritization: "What is one thing I would regret not doing?"
22:47 Prioritizing at home versus at work, and whether kids made them better professionals
26:48 Why Dana disagrees that you need to be "AI-pilled" to get an AI job
31:51 Hemal's three skills of a great PM: historian, technologist, anthropologist
33:04 Why curiosity and adapting to change as the traits that matter even more now
35:41 How to stay current: the job itself and Hemal's "people curation"
42:38 JZ on why unique data is the moat at Laurel
45:58 Hemal's playbook: data, distribution, people, and a company willing to change
49:41 JZ's advice: take the forward-deployed or AI operations role, not just the PM title
51:12 Early-career advice: your next job is forward deployed at a startup you've never heard of
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Brought to you by:
• Firecrawl—Gives your AI agents data from the web and beyond: Redeem your SKIP coupon in the Firecrawl dashboard to get 10,000 Firecrawl credits under Settings → Billing → Coupons
• Stripe Treasury: Bring payments and finances together
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Referenced:
• Airbnb
• Decagon
• Google
• Grit
• Harvey
• Laurel
• OpenAI
• OpenClaw
• Reforge
• Sierra
• SNOO
• Webflow
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Where to find Nikhyl:
• LinkedIn
–
Where to find Dana:
• LinkedIn
–
Where to find Hemal:
• LinkedIn
–
Where to find JZ:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comInside PM at Anthropic: Who Makes It, and Who Doesn’t
In this episode, Dianne Na Penn, who leads product for Anthropic's research and labs teams, joins me for the fifth conversation in the "Inside PM" series. Dianne joined Anthropic in 2023 as its first technical …
Notes de l’épisode
In this episode, Dianne Na Penn, who leads product for Anthropic's research and labs teams, joins me for the fifth conversation in the "Inside PM" series. Dianne joined Anthropic in 2023 as its first technical product manager, and her team has since run product on every model from Claude 2 through the Claude 5.5 family and helped incubate Claude Code, MCP, Skills, and Claude Design. We get into who makes it as a PM at Anthropic and who doesn't, why early-career PMs and former forward-deployed engineers have an edge, and how her team keeps up the pace without burning out.
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Key topics:
• Why the first two months should feel like "some of the hardest of your career"
• What trips up PMs from big, hierarchical companies, and how to question assumptions "in a graceful manner"
• Why early-career PMs are "extremely effective and high ceiling"
• Forward-deployed engineers who moved into product, and why they've been exceptional PMs
• Dogfooding prototypes instead of writing PRDs in the corner
• Running on monthly plans against assumptions three to six months out
• Claude Code wasn't a one-day leap: from autocomplete to agentic loops in the terminal
• When the next model will fix it: "an incredibly dissatisfying answer as a PM"
• The bootcamp on building products that "ride the exponential"
• Working sustainably with PM pods, copilots, and team days off
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Timestamps:00:00 Introduction02:35 From bond trader to Credit Karma, Alexa AI, and Anthropic08:22 Problems that are 1% solved, not 95% solved11:04 Advice for strategists: "the 99% is after you write the initial plan"13:18 Planning when the industry shifts every six weeks16:30 How bets like Claude Code become products21:37 Who Dianne hires: meandering careers and first PMs at startups23:12 "The first two months here should feel like some of the hardest of your career"24:27 What trips up PMs from big, hierarchical companies26:54 Questioning assumptions: a skill the work demands, or Anthropic culture?30:01 Why early-career PMs are "extremely effective and high ceiling"33:42 What Google's early APM program says about PM at Anthropic36:30 Onboarding: users, an eval, and a roadmap in the first two to three weeks39:13 Inside the bootcamp on building products that "ride the exponential"41:31 A live question: balancing research priorities with user feedback47:03 Training standups with research leads: is it a P0 or a P2?49:20 Should PMs be forward deployed?54:07 Working sustainably: real time off, team days off, and PM pods
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Brought to you by:
• Chargebee—Billing and monetization infrastructure for the AI era
• Stripe Treasury—Bring payments and finances together
–
Referenced:
• Claude
• Gemini
• Google's Associate Product Manager (APM) Program
• Intuit
• Model Context Protocol (MCP)
• Why Software Is Eating the World
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Dianne:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comJob-Search Advice Now Expires Every Six Months
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 …
Notes de l’épisode
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.”
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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
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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
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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
• ChatGPT
• Claude
• Google
• Meta
• OpenAI
• Runway
• Three Job Searches, Three AI Roles
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Where to find Nikhyl:
• LinkedIn
–
Where to find Anthony:
• LinkedIn
–
Where to find Gadi:
• LinkedIn
–
Where to find Chandra:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comThree Top Executive Recruiters on Where Product Management Is Going
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 …
Notes de l’épisode
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.
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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
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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
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Referenced:
• a16z
• Abridge
• Airbnb
• Airtable
• Atoms
• Autodesk
• ChatGPT
• Claude
• Cursor
• Datadog
• Daversa
• Decagon
• DoorDash
• Figma
• Google
• Gusto
• Harvey
• Meta
• Miro
• Nash
• OpenAI
• Sierra
• Square
• Substack
• Uber
• Vercel
• xAI
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Brought to you by:
• Chargebee—Billing and monetization infrastructure for the AI era
–
Where to find Nikhyl
• LinkedIn
–
Where to find Lindsay
• LinkedIn
–
Where to find Andrew
• LinkedIn
–
Where to find Caroline
• LinkedIn
–
Join The Skip
–
Find The Skip
• Website
• Substack
• YouTube
• Spotify
–
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.comInside Gemini: How Google Runs Product for Its Model
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 …
Notes de l’épisode
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.
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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"
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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:
• Gemini
• Gmail
• Google
• Google's Associate Product Manager (APM) Program
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Tulsee:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comWhat the Past Year Taught Meta
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 …
Notes de l’épisode
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.
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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
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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
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Brought to you by:
• Jira—Do the right work with Jira
–
Referenced:
• Bolt
• Facebook
• Google
• How Meta Is Reinventing Product Management
• Lovable
• Meta
• Replit
• Threads
• TikTok
• WhatsApp
• YouTube
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Jagjit:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comTo Invent Waymo, They Had to Reinvent PM
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 …
Notes de l’épisode
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.
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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
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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
• MMLU
• NASA
• Waymo
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Saswat:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comLessons From Three Product Leaders Living in the Future
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 …
Notes de l’épisode
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.
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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
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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:
• Cursor
• Devin
• Dropbox
• Dust
• GitHub
• Grain
• Granola
• Laurel
• Meta
• Mutiny
• Notion
• Slack
• Stripe
• Twitch
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Sharmeen:
• LinkedIn
–
Where to find JZ:
• LinkedIn
–
Where to find Henrik:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comInside PM at Stripe: What Comes After "Become a Builder"?
Kevin Yien is the Head of Product for Merchant Experiences at Stripe. Before that he led Product at Mutiny and Square. In this episode, Kevin and I discuss how to keep AI from becoming theater, why a PM …
Notes de l’épisode
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.
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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:
• Block
• Dovetail
• GitHub
• Lovable
• Obsidian
• Stripe
• v0
• Writer
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Kevin:
• LinkedIn
• Website
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comBuilder-Executives Are Getting Paid Like Pro Athletes
Product pay is detaching from the old bands the way it did for AI researchers. In the past few weeks I've seen three offers go out to product executives at $10 million a year, and while almost nobody gets that …
Notes de l’épisode
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:
• Meta
• OpenAI
• Stripe
–
Where to find Nikhyl:
• LinkedIn
–
Where to find Carly:
• LinkedIn
–
Join The Skip:
–
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
–
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.comHow Meta Is Reinventing Product Management
Meta is one of the biggest dinosaurs in the park, yet in a matter of months it rebuilt PM top to bottom, and almost none of it was bought. My guest is Jagjit Chawla, a VP of Product at Meta who’s running a …
Notes de l’épisode
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:
• Facebook
• Ferrari
• Gmail
• Google
• Meta
• Porsche
• TikTok
• Zoom
Where to find Nikhyl:
• LinkedIn
Where to find Jagjit:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
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.com5 Career Questions Your Old Playbook Can’t Answer
In today's episode, we work through five questions from leaders in the Skip community who are doing well by any measure: a director whose career keeps ending in short stints despite strong performance, a …
Notes de l’épisode
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:
• 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:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
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.com10 Job-Search Rules That Just Broke
In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding …
Notes de l’épisode
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
• LinkedIn
Where to find Dana
• LinkedIn
Where to find Briana
• LinkedIn
Where to find Pei-Chin
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
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.comThe product skill you must now master: Reinvention
If you're in a career transition right now and wondering whether you did something wrong, you didn't. Every question coming into Nikhyl.AI keeps circling the same idea: do I really have to reinvent? In today’s …
Notes de l’épisode
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
Where to find Carly
Join The Skip
Find The Skip
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.comWhat PM Hiring Managers Actually Screen For
Most interview advice tends to come from the candidate’s perspective - how to prep, share your experiences, and follow up. This conversation pulls back the curtain on the other side of the table. I spoke with …
Notes de l’épisode
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
• LinkedIn
Where to find McKenzie
• LinkedIn
Where to find Sam
• LinkedIn
Where to find Sarah
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
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.comHow to Navigate Org Drama
Work getting political isn't new, but surviving it without derailing your career has never been more challenging. As organizations flatten and restructures accelerate, the instincts that used to work — push …
Notes de l’épisode
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
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
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.comThe Post-IPO PM Playbook Is Being Rewritten
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 …
Notes de l’épisode
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
• LinkedIn
Where to find Anneka
• LinkedIn
Where to find Dheerja
• LinkedIn
Where to find Yuhki
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
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.comThree Job Searches, Three AI Roles: What Actually Worked
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 …
Notes de l’épisode
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
• LinkedIn
Where to find Ben
• LinkedIn
Where to find Janie
• LinkedIn
Where to find Julia
• LinkedIn
Join The Skip
Find The Skip
• Website
• Substack
• YouTube
• Spotify
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.comThe Promotion Mistakes That Derail PM Careers
It's promo season, and I've gotten roughly 1000 questions through nikhyl.ai—the pattern is unmistakable: people aren't just asking how to get promoted, they're asking whether the system is broken and whether …
Notes de l’épisode
It's promo season, and I've gotten roughly 1000 questions through nikhyl.ai—the pattern is unmistakable: people aren't just asking how to get promoted, they're asking whether the system is broken and whether they should quit over it. In this episode, we dissect five real questions from PMs who've been passed over. What becomes clear is the mistakes aren't in execution—they're in how people think about promotions in the first place. The tough reality is promotions are harder to get in this market. The question isn't whether you'll get promoted. It's how you respond when you don't.
Key topics
• Why promotions are harder now—and why that's not dysfunction
• The five-point framework for what to do when you don't get promoted
• The self-fulfilling prophecy that derails your career
• The one question that changes everything when you're passed over
• Why treating promotion as a game to win backfires
• The Peter Principle: why companies make you prove it before they promote you
• When "my career has flatlined" actually means you've hit the expected difficulty curve
• Why the skills that got you here won't get you there
• Why leadership might not be your destination—and that's okay
• The feedback gap: why your manager says you're great but leadership won't promote you
• Why leaving gas in the tank puts your career at risk
• Why you work for the company, not your manager
• What to do when your skip starts building a case against you
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:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:00) Why you're not being promoted
(03:42) Why promo season brings more angst than any other time of year
(04:57) Question 1: L5 at Google denied promotion twice—is this organizational dysfunction?
(06:22) Why assuming your company is broken becomes a self-fulfilling prophecy
(09:50) What to do when there's literally no next-level job in your location
(11:45) Question 2: Six years at my company, seven rounds of interviews—still passed over for Executive Director
(14:06) The Peter Principle: why companies make you demonstrate next-level skills first
(17:18) Why promotion as a game to win is dangerous thinking
(21:12) When you've hit the ceiling—and that might be okay
(24:41) What to avoid when being passed over
(26:48) Question 3: I'm on track for promotion but political meetings drain my energy
(27:57) When the next level isn't for you—finding companies where leadership looks different
(32:11) Question 4: Three years since my last promotion to PPM—has my career flatlined?
(32:58) Why the IC-to-leader skill gap takes years to close
(35:50) The soft skills problem: leadership presence can't be taught in a class
(36:56) Question 5: My skip is suddenly giving me feedback my manager never mentioned
(38:42) Why you should never leave gas in the tank
(43:30) You work for the company, not your manager—why that matters
(45:25) The five biggest mistakes to avoid when you don't get promoted
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.comThe PM Career Framework for AI (Part 3): AI Labs to Founding
The "join a hot company" narrative gets even more complicated once you enter the AI-native part of the market. In Part 3 of our PM Career Framework for AI series, we close out with the doors everyone's …
Notes de l’épisode
The "join a hot company" narrative gets even more complicated once you enter the AI-native part of the market. In Part 3 of our PM Career Framework for AI series, we close out with the doors everyone's obsessing over: AI labs, hot AI startups, ex-growth companies, and founding.
We unpack what these companies actually look for (spoiler: it's not "AI experience"), why hands-on builders win over managers, how location and pace become make-or-break constraints, and how to think about risk and chaos when the upside is real.
If you're trying to figure out whether you should stay put in 2026, or make the leap into the AI frontier, this episode breaks down the tradeoffs.
Key topics
• What AI labs are really hiring for (and why "productized research" is the core skill)
• Why AI labs want radically hands-on PMs, not managers
• Why Big Tech experience can become "inside-the-building skills" that don't translate
• Which companies expect 9-9-6 culture, and the self-selection problem it creates
• Why some struggling-company VP roles are still worth taking
• When equity becomes a psychological trap (and when to cut losses)
• Why remote leadership roles are rapidly disappearing
• The founder litmus test: why it's an emotional decision, not a spreadsheet decision
• The upside of founding even when it fails: the career story compounding effect
Where to find other the parts of this series:
• Part 1: https://theskip.substack.com/p/the-pm-career-framework-for-ai-how
• Part 2: https://theskip.substack.com/p/the-pm-career-framework-for-ai-part
Where to find Nikhyl:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:58) The “doors” framework: building a personal stack rank for AI
(04:57) The “productized research” skill: turning magic into product
(08:29) Why AI labs want hands-on builders, not managers
(15:00) Does AI domain expertise matter?
(19:14) Location constraints: The SF requirement for PM roles
(21:39) The Atlassian → OpenAI decision: Upending everything for the skip job
(30:16) Inside the high pace at AI Labs
(32:00) Hot AI Startups: the IC role that’s a step forward
(39:12) The 9-9-6 Reality: who's actually doing it
(41:59) The power years problem: Gender, biology, and self-selection
(46:13) The brand value of hot AI startups
(48:32) When equity becomes a psychological trap (and when to cut losses)
(54:12) Why some struggling-company VP roles are still worth taking
(58:53) Why remote leadership roles are declining
(63:10) The ex-growth equity risk: Why your compensation might never materialize
(65:24) Choosing between YC offer vs AI lab internship vs college
(73:41) The founder litmus test: why it's an emotional decision, not a spreadsheet decision
(80:24) When to join vs found
(82:31) Constraints + doors = your personalized career advice
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comThe PM Career Framework for AI (Part 2): The Large Tech Playbook
The “join a hot company” career narrative is getting a lot of PMs into trouble. In Part 2 of our PM Career Framework for AI series, we get practical: how to pick the door that fits you — and spot when a …
Notes de l’épisode
The “join a hot company” career narrative is getting a lot of PMs into trouble. In Part 2 of our PM Career Framework for AI series, we get practical: how to pick the door that fits you — and spot when a prestigious logo is quietly costing you career momentum. We break down nearly 600 listener questions, then map the first set of doors, from Big Tech and public enterprise to the “quality middle” of elite private companies and recent IPOs.
Key topics
• The “doors” framework: building a personal stack rank
• Golden handcuffs: when staying in Big Tech is rational
• Why L7+ doesn’t translate to startups or AI labs
• The “step down” that’s actually a level up
• How to know if you’re a fit for AI-native companies
• Debunking the myth of “coasting” in Big Tech
• Why APM programs can be the fastest way to learn the craft
• The stay/leave test: can you produce a career story?
• Who is suited to public enterprise tech
• The “quality middle” sweet spot
What’s next (Part 3):
Next episode, we assess the doors everyone’s obsessing over: AI labs (OpenAI / Anthropic), hot AI startups, ex-growth mid-stage companies, and founding. We will also cover why the rules change dramatically once you move into the AI-native part of the market.
Where to find Nikhyl:
Where to find Carly:
Join The Skip:
Find The Skip:
Timestamps
(00:46) The “doors” framework: building a personal stack rank
(11:50) Golden handcuffs: when staying in Big Tech is rational
(17:12) Why promotion often doesn’t translate to your next job
(19:29) The “step down” that’s actually a level up: from learning to teaching
(22:55) How to upgrade your product intuition without quitting your job
(26:23) The Big Tech fit test: why some builders struggle (and some thrive)
(31:03) Early-career exception: why APM programs can accelerate you
(34:26) Career stories: opinion → ship → impact → learning (and how to collect them)
(39:17) Public enterprise tech: when stability + liquidity is the smart move
(42:30) The hard question: are you unlucky, or are you the problem?
(48:44) If your company is behind on AI: be the change agent or move on?
(53:49) The “quality middle” sweet spot: elite teams, near-liquidity, durable brands
(57:55) Domain expertise vs “chasing AI”: where you’ll have the most impact
(62:17) Builder vs fixer: choosing the work you’re actually signing up for
(65:03) Key takeaways + what’s coming in Part 3
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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.comThe PM career framework for AI
The old PM career playbook doesn’t work in the AI era. In this episode of The Skip, we lay out a new career framework for product managers, and it’s a lot more “choose your door” than “climb the ladder.” If …
Notes de l’épisode
The old PM career playbook doesn’t work in the AI era. In this episode of The Skip, we lay out a new career framework for product managers, and it’s a lot more “choose your door” than “climb the ladder.” If you’re wondering whether to stay in big tech, jump to an AI startup, double down as a builder, or rethink your whole path, this one’s for you. We talk about why your hard-won product intuition is quietly becoming obsolete, why some ex-VPs are happily taking senior IC roles, and how to prepare for what’s coming next.
Key topics
• Why your product intuition is outdated — and how to “go back to school” without quitting your job
• Why company quality now matters more than your title, comp band, or level
• What elite AI companies are actually looking for in PMs
• The builder vs factory mindset: are you obsessed with the product, or with the machine that ships it?
• How to choose between Big Tech, hot AI startups, healthy growth companies, or founding
• A three-part reality check on constraints: compensation, location, and pace
• The truth about 9–9–6 and AI startups: when extreme pace is worth it, and when it’s just branding
• Why “coasting” in big tech is mostly a myth
• Remote vs hub tradeoffs: what you gain and lose by moving to SF or NYC
• Why this is Part 1 — and what we’ll go deeper on next in the PM Career Framework for AI series
Where to find Nikhyl:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
Timestamps
(00:53) Why the PM career framework needs to be rewritten for AI
(03:35) Why ex-VPs are happily taking senior IC roles
(06:07) Why your current product intuition is becoming obsolete
(11:46) Why AI-first companies only want hands-on PMs
(14:40) How to choose between Big Tech, AI startups, growth companies, or founding
(18:06) How to actually upgrade your product intuition on the job
(25:13) What’s really happening with PM compensation in 2025
(33:46) Why true AI startups are rarely remote-first
(42:42) What 9–9–6 culture at AI companies actually looks like
(50:52) The myth of work–life balance in growth environments
(55:40) The builder vs factory mindset
(60:29) Are you obsessed with the product or the factory that ships it?
(67:11) The key takeaway for PMs making career moves in 2025
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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.comWhy your career playbook expired: The new rules for 2025 job transitions
Career ladders aren't just changing—they're being demolished and rebuilt in real-time. In this emergency "weather report," Carly and I decode four career dilemmas that have completely flipped in the last six …
Notes de l’épisode
Career ladders aren't just changing—they're being demolished and rebuilt in real-time. In this emergency "weather report," Carly and I decode four career dilemmas that have completely flipped in the last six months. We explain why directors are taking IC roles (and thriving), why your Big Tech salary might be a golden trap, when to finally leave that stalled growth company, and why founding is suddenly on everyone's radar. If you're making any career move in 2025, your old playbook will hurt more than help.
The New Career Math:
• Why senior IC roles now trump management positions—and when stepping down is stepping up
• The Big Tech paradox: 3x market comp but career stagnation (what's your breaking point?)
• Ex-growth company reality: Why staying another month makes things worse
• The founding surge: Why 8x more product leaders are starting companies
What's Actually Happening:
• How AI and flat orgs killed the traditional ladder (and what replaced it)
• What elite companies want now: hands-on builders, not ivory tower managers
• The talent gravity effect: Why your coworkers matter more than your title
• The "elite middle" strategy: Which companies offer both growth and stability
Your Action Plan:
• How to evaluate if you're becoming obsolete (and what to do about it)
• The unnatural acts worth taking (hint: it involves a pay cut)
• Six-month forecast: Where the opportunities will be and who will win
Timestamps:
(03:45) The rise of Super ICs
(07:59) Why IC roles are considered premium
(18:56) “I work at Google: should I stay, or should I go?”
(27:05) How Nikhyl gives career advice to tech leaders
(31:12) What are startups hiring for?
(37:10) Why are more people leaving ex-growth companies?
(42:21) Advice for choosing the right company to join
(46:24) You need to work with great talent
(48:21) How to navigate the wealth of career options
(52:37) The career trap you need to avoid
(56:29) Should you found a company?
(59:09) Nikhyl’s forecast for the next six months
Where to find Nikhyl:
• LinkedIn
Where to find Carly:
• LinkedIn
Join The Skip:
Find The Skip:
• Website
• Substack
• YouTube
• Spotify
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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.comGraduating Into Uncertainty? How to Actually Land Your First Tech Job
In this episode, I’m joined by my co-host Carly Malatskey to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone …
Notes de l’épisode
In this episode, I’m joined by my co-host Carly Malatskey to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone who is — this episode is for you.
–
Key topics
• Why your first job should feel like a sprint, not a stroll
• How to tell if your job is setting you up — or holding you back
• The truth about internships (they matter more than your degree)
• How to stand out when applying — and why “spray and pray” fails
• Why it’s okay (even smart) to view your first job as a stepping stone
• Red flags and green flags once you’re hired
• How to network in a way that doesn’t feel transactional
• The mindset shift that separates top performers early in career
• Why working in-person still gives you an edge
• How to take real risks when you have the least to lose
–
Where to find Nikhyl:
–
Where to find Carly:
–
Join The Skip:
–
Find The Skip:
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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]
–
Timestamps
(00:00) Why most grads feel lost — and what to do about it
(01:44) How to navigate the 2025 job market
(03:29) Why hustle still wins (yes, even now)
(08:24) What to really look for in your first job
(15:03) Why seeking feedback is a career unlock
(17:30) Choose your boss — not the logo
(20:02) Why taking risks early pays off later
(28:35) How to tell a compelling career story
(32:15) Job hunting that actually works
(37:38) Making the leap from college to career
(42:18) Why you should work while studying
(46:13) How to maintain a network
(55:10) Green flags and red flags once you’re hired
(58:55) Your first job is a launchpad — not a life sentence
(63:12) Final advice we wish we heard at 21
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comThe Mentor's Superpower: Pattern Recognition That Unlocks Careers
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others …
Notes de l’épisode
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others miss, and how you can use that insight to unlock your next move. Whether you're leading a team, switching paths, or just feeling off, this episode is packed with tactical advice for unlocking your career.
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Key topics
6 common patterns holding leaders back
How mentors can spot them, and what advice to give
Breaking through organizational barriers
Why smart people still get stuck
Navigating change vs. waiting it out
Thriving in early-stage chaos
Why strong reviews don’t always lead to promotion
Taking leadership roles before you feel ready
Finding—and becoming—a great mentor
How to ask better questions and get better advice
–
Where to find Carly:
–
Where to find Nikhyl:
–
Find The Skip:
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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]
–
Timestamps
(00:00) How to spot patterns
(01:08) How to find and then become a mentor
(10:57) Scaling mentorship
(15:09) How to heat seek around patterns
(21:47) Question 1: How can I break through organizational barriers?
(22:29) Pattern 1: Are you actually stuck?
(30:05) Question 2: How can busy leaders stay technically up to date?
(30:28) Pattern 2: If you know what you should do, why aren’t you doing it?
(42:48) Question 3: How to navigate change?
(40:56) Pattern 3: Do you need to work on this problem, or just wait it out?
(52:23) Question 4: How normal is chaos in early stage companies?
(52:54) Pattern 4: Broken might be normal, and you were hired to solve problems
(61:07) Question 5: My performance reviews are excellent, but why am I not being promoted?
(61:41) Pattern 5: Are you growing faster than the company?
(67:35) Question 6: Should I take a leadership role that I don’t feel ready for?
(68:29) Pattern 6: Are you too humble or negative?
(73:23) Key takeaways and summary
(77:57) How to get in touch with Nikhyl
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comSuper Shadows | When Strengths Limit Growth
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to …
Notes de l’épisode
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to shifting expectations. Using a structured approach, we break down when to make a change, how to advocate for yourself, and how to evolve without losing what makes you successful. Whether you’re navigating subtle shifts or considering a big move, this episode helps you own your superpower—and the shadow that comes with it.
–
Key topics
- The unseen influence of Super Shadows
- Why past success won’t fuel future growth
- Breaking free from career stagnation
- The power of self-advocacy
- How top leaders seek feedback
- Identifying what actually needs to change
- Much more
–
Where to find Carly:
–
Where to find Nikhyl:
–
Find The Skip:
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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]
–
Timestamps
(00:00) How your superpower can stall career growth
(01:11) Show format
(02:45) Listener question: Navigating a quiet career crisis
(06:40) How to break free from feeling stuck at work
(11:35) The case for self-advocacy in your career
(16:36) Why past success won’t fuel future growth
(19:48) Super Shadows: What they are and why they matter
(30:46) When it’s time to confront your shadow
(37:53) The risks of ignoring your shadow
(40:56) How great leaders seek feedback
(47:07) Pinpointing what actually needs to change
(55:57) A strategy for sustainable career growth
(57:04) Why change has to happen on the job
(58:19) A real-world example from Nikhyl’s offsite
(61:28) Key takeaways and final thoughts
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comShould you Stay or Go? A 5-factor framework for career-defining decisions
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or …
Notes de l’épisode
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisions based on compensation, skills, lifestyle, long-term success, and work environment. Whether you’re considering a career move now or just want a structured way to assess future opportunities, this episode offers a practical guide to making confident job decisions.
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Key topics:
- The Stay vs. Go framework for career decisions
- How to assess if your job is career additive
- Balancing comp, skills, and lifestyle in job choices
- The probability of success matters in career moves
- How long you should stay before making a switch
- And much more
–
Where to find Carly:
–
Where to find Nikhyl:
–
Find The Skip:
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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]
–
Timestamps
(00:00) The 5-factor framework
(01:20) Mailbag question: “Should I stay or go?”
(03:38) Is your job career additive?
(09:52) Why tenure matters less for some people
(15:51) Framework overview
(17:21) How to think about compensation
(21:28) Fishing for outlier comp offers
(23:54) Don’t just optimize for comp
(25:46) What skills are you picking up
(30:09) How esoteric are your skills
(32:37) Weighing up lifestyle
(36:56) What’s the probability you will succeed?
(42:03) Think about the environment you thrive in
(44:54) Final advice
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comThe Insider's Guide to Tech Compensation, Negotiation, and Career Growth
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We dive into a listener's question about multiple tech job offers, and …
Notes de l’épisode
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking to understand tech compensation better, this episode offers practical insights for making informed career decisions.
–
Key topics:
- Why chasing comp early hurts career growth
- Comparing job offers
- Breaking down key components of total comp
- Ensuring you can exercise your shares
- When and how to discuss salary expectations
- Much more
–
Referenced:
–
Where to find Carly:
–
Where to find Nikhyl:
–
Find The Skip:
–
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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]
–
Timestamps
(00:00) Tactic for negotiating comp
(01:54) Unpacking the mailbag format
(03:09) Three job offers: which one should I take?
(06:02) Understanding bonus structures
(09:32) Why equity still matters today
(17:38) Breaking the equity exit trap
(25:29) Equity versus your market rate
(30:37) Don't chase comp early on
(34:12) Aligning the role to your superpower
(37:47) Negotiating comp: Start with what matters most
(47:30) When to discuss salary
(51:49) Problems with averaged comp
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comThe Widening Tech Career Divide: Big vs Small Tech
In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor and podcast host of She Leads. We dive into one of the most important career questions in tech today: Should you work in big tech or …
Notes de l’épisode
In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor and podcast host of She Leads. We dive into one of the most important career questions in tech today: Should you work in big tech or small tech, or found your own company? With the rise of AI and new economic conditions, these choices have never been more different. We break down how industry dynamics have changed, the tradeoffs associated with each path, and some exercises for determining the best fit for you.
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Key topics:
- How AI is reshaping the tech job market
- The (under-appreciated) differences between big tech and small tech
- How PM and engineering roles have changed
- How to assess your potential as a founder
- What your worries reveal about your ideal work environment
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Referenced:
- Carly’s podcast: https://www.sheleadspod.com/
- Ready to start a startup?: https://www.skip.show/ready-to-start-a-startup-shreyas-doshi-former-pm-leader-at-stripe-twitter-google/
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Where to find Carly:
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Where to find Nikhyl:
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Where to find The Skip:
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Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
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Timestamps:
(00:00) Teaser: Big tech vs small tech: Should you do both?
(00:35) Intro
(03:15) Why this discussion matters
(05:06) The biggest change in tech during 2024
(08:20) Why everyone should consider being a founder
(10:14) How to assess your potential as a founder
(14:44) How PM & engineering changed in 2024
(23:06) The all-important differences between big and small tech
(28:55) Assessing your fit for big vs small tech
(36:18) The challenges and benefits of working at both scales
(42:31) Do the best PMs work in big tech?
(52:17) Who this advice doesn't apply to
(54:56) Key takeaways
(56:33) Get in touch with Nikhyl
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.comReady to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)
I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why …
Notes de l’épisode
I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders.
Key topics:
- Which PMs are secretly great founder material
- Red flags: when founding isn't for you
- The right time to start your company
- Key skills that set you up for success
- Thriving in ambiguity
- Debunking the "venture scale or bust" mindset
- The counterintuitive way to avoid burnout
- Much more
Referenced:
- 4 questions Shreyas wished he’d asked himself sooner: https://www.youtube.com/watch?v=atS060bNpE0&t=698s
- Avoiding burnout for high achievers: https://www.youtube.com/watch?v=5Iwymgai-ZM
- Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928s
- Improving your product sense: https://maven.com/shreyas-doshi/product-sense
- Is my next job at a startup or big tech?: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s
- Managing your PM career in 2025 and beyond: https://maven.com/shreyas-doshi/product-management-career?utm_source=lenny
- Nikhyl’s career advice highlights at Lenny’s Summit: https://www.youtube.com/watch?v=rujK7HvD6es&t=124s
- Stage of Company: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s
Where to find Shreyas:
Where to find Nikhyl:
Find The Skip:
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. 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]
Timestamps
(00:00) Teaser: Why average PMs can make great founders
(01:17) Introduction
(02:34) The essential first step before founding
(06:21) Successful founder traits
(10:48) Managing at scale vs managing uncertainty
(18:25) Thriving in ambiguity
(21:29) Red flags: when founding isn't for you
(23:34) The surprising link between average PMs and founding success
(25:51) Building better product sense
(29:35) The right time to start your company
(37:03) Beyond venture scale: rethinking startup success
(44:26) A guide to avoiding burnout
(49:23) The real truth about big tech working hours
(52:27) Why taking a "demotion" might be a good move
(58:45) Learn more: Shreyas' Product Sense course
(63:15) Key takeaways
(65:22) Get in touch with Nikhyl
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
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