The Skip Podcast – Details, episodes & analysis

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

Key topics

• Why you need curiosity, not experience

• The "AI hungry" mindset: searching for environments that match your learning goals, not just your resume

• Why the best job search intelligence comes from people who just landed, not people still looking

• Why prototypes are now table stakes in take-homes

• How Janie built a shortlist of 5–10 companies in a week of 50–60 conversations

• Why Ben's Netflix role traces back to a cold application seven years ago

• What OpenAI's interview process actually looks like—and why it's less about the past than you expect

• Why most AI-native jobs aren't posted, and how to land them

• How to use investor attention as a proxy for company quality

• Why Ben's early interview mistake (not enough AI mindset) became the fuel for his take-home

Brought to you by

• Framer—Build websites with enterprise needs at startup speeds: https://framer.link/dFacxBQ

• Dust—The operating system for AI agents: https://dust.tt/skip

Where to find Nikhyl

• Twitter/X

• LinkedIn

Where to find Ben

• LinkedIn

Where to find Janie

• LinkedIn

Where to find Julia

• LinkedIn

Join The Skip

• Skip Coach

• Skip Community

Find The Skip

• Website

• Substack

• YouTube

• Spotify

• Apple Podcasts

Timestamps

(00:00) How to prove your AI credentials

(04:42) Introducing the three product leaders

(06:00) Ben Dreier: from DoorDash to Netflix, the "AI hungry" move

(08:18) Julia Roberts: nine years at Pinterest, six months off, then OpenAI

(12:46) Janie Lee: going all-in on AI native at Abridge

(15:26) How to build a shortlist: 50–60 conversations in a week

(18:10) Ben's process: VC signals and insider conversations over job boards

(21:45) Cold outreach that actually works

(23:51) Ben: how curiosity, not networking, built his network

(25:14) Julia's different path: cold applies, inbound, and exec recruiters

(27:06) What exec recruiters are actually useful for

(30:30) Ben's Netflix backstory — tracing back to a cold apply seven years ago

(34:06) Staying connected with recruiters, coworkers, and people who said no

(41:10) What the OpenAI interview process actually looks like

(44:55) Authentic storytelling

(46:40) The Netflix take-home: how mid-process feedback became a turning point

(51:40) Janie: how to ace take-homes by using AI

(57:52) Julia’s final takeaway: know what you want before you search

(59:03) Ben’s final takeaway: follow the fun and genuine curiosity

(59:56) Janie’s final takeaway: high agency, high effort, put yourself in their shoes

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community

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:

• Twitter/X

• LinkedIn

Where to find Carly:

• LinkedIn

• She Leads Podcast

• Twitter/X

Join The Skip:

• Skip Coach

• Skip Community

Find The Skip:

• Website

• Substack

• YouTube

• Spotify

• Apple Podcasts

Timestamps

(00:00) 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 nikhyl@skip.community

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.

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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

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Referenced:

• Tech compensation: Beyond the offer letter

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Where to find Carly:

• LinkedIn
• She Leads Podcast
• Twitter/X

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Where to find Nikhyl:

• Twitter/X
• LinkedIn

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Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

–

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 nikhyl@skip.community

–

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

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:

• LinkedIn
• She Leads Podcast
• Twitter/X

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Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

-

Where to find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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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

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:

• Twitter/X
• LinkedIn
• YouTube

Where to find Nikhyl:

• Twitter/X
• LinkedIn

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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 nikhyl@skip.community

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

Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months. In this highlight reel of career advice, I discuss:

• Rethinking retirement
• The career-defining question every leader should ask
• Power years versus foundational years
• Leveraging career stories
• Finding peak roles
• Understanding the shadow of your superpower
• The relationship between personal brand and reputation
• Breaking down burnout
• Building your support network through Skip Community

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Referenced:

• Mastering your 30s career resume
• 4 secrets of career boosting companies
• Avoiding burnout for high achievers
• Battling job search anxiety
• Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)
• Crafting a compelling career story
• JZ: https://www.linkedin.com/in/jiaona/
• Shadows of your superpowers (Part 1)
• Shadows of your superpowers (Part 2)
• Shedding perceptions: Moving from lone wolf to team player
• Six superpowers of product managers
• Stage of company: A career unlock
• The art of building your personal brand

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Where to find Nikhyl:

• Twitter
• LinkedIn

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Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

–

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 nikhyl@skip.community

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Timestamps:

(00:00) How to help the Skip community

(01:37) Lenny’s Summit

(04:10) Breaking your career into levels

(07:33) Crafting a compelling career story

(10:26) All elite PMs find “peak roles”

(12:15) “The reputation you build today is the brand you’ll have tomorrow”

(13:17) Avoiding burnout

(16:13) Knowing the shadow of your superpower

(18:13) Don’t build a career alone

(18:53) Summary of advice

(20:19) Special announcement

A great career story can accelerate growth, yet most struggle to craft one. Even top performers fall short, telling stories that are overly detailed, abstract, jargon-filled, or poorly structured – all of which can lose a listener's interest.

The first 30 seconds are crucial; you need to hook your audience quickly. Think of the beginning of your story as a movie trailer: highlight the most engaging aspects rather than chronologically detailing every event.

This episode focuses on crafting a captivating 30-second introduction to your career story that engages listeners and enhances your professional profile. We've taken a unique approach by inviting Skip community members to submit their career stories for a live workshop. You'll hear real examples of me coaching engineering and product leaders, demonstrating the transformation from initial attempts to polished and punchy narratives.

We also discuss:

• Common storytelling mistakes that everybody makes
• Techniques for weaving a theme into your story
• Effective strategies that will hook listeners
• Adapting your story for various audiences and situations
• Balancing between brevity and showcasing your unique value

Referenced:

• Crafting a compelling career story
• Founder Mode, done right with Shreyas Doshi

Where to find Nikhyl:

• Twitter
• LinkedIn

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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 nikhyl@skip.community

Timestamps

(00:00) Episode teaser: Mastering your 30s resume

(01:15) Common mistakes everybody makes

(09:42) Why you need a 30s and 2m career story

(12:21) Showing the trailer, not the movie

(16:44) Example 1

(17:28) Thinking about story sequencing

(19:04) Example 2

(19:44) Avoiding detail

(21:21) Example 3 (before)

(21:54) Avoid abstract stories

(23:52) Example 3 (after)

(24:41) The art of thematic narratives

(28:29) Example 4 (before)

(29:18) Crafting a theme

(29:51) Example 4 (after)

(31:24) Avoiding jargon

(34:51) Tailoring communication tempo

(36:19) Example 5 (before and after)

(39:04) Example of a strong 30s resume

(41:13) Preparing multiple versions

(45:20) Nikhyl’s strong but generic resume

(47:50) Nikhyl’s deeper version

(50:57) How to submit your career story

(52:50) Get in touch with Nikhyl

In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders.

We also discuss:

• Why founder mode is a mindset, not a title
• Whether founder mode is good or bad
• Balancing detail and delegation
• The importance of product sense and good judgment
• Mastering founder mode as a product leader
• Operational insights from Meta and Stripe

Referenced:

• Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928s
• Paul Graham’s "Founder Mode": https://paulgraham.com/foundermode.html
• Shreyas’ Tweet on founder mode’: https://x.com/shreyas/status/1830767630917214318
• Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-c
• Shreyas’ previous appearance on the podcast: https://www.youtube.com/watch?v=y_TnXtnY3QM&t=23s
• The 3 types of product leaders: https://x.com/shreyas/status/1375491623308550144

Where to find Shreyas:

• Twitter/X
• LinkedIn
• YouTube

Where to find Nikhyl:

• Twitter/X
• LinkedIn

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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 nikhyl@skip.community

Timestamps

(00:00) Teaser: Unpacking founder mode

(02:47) What Shreyas has been up to

(04:04) Shreyas’ take on founder mode

(08:59) Why judgment and product sense is critical

(13:04) Balancing detail and delegation

(20:57) The key question for founders about ownership

(23:01) Not every company needs a CPO or Head of Product

(28:07) When product people should prioritize detail

(31:32) What everyone gets wrong about Steve Jobs

(34:22) Shreyas’ observation about John and Patrick Collison

(38:17) Nikhyl’s observation about Mark Zuckerberg

(40:05) Founder vs manager mode

(43:40) Should leaders avoid manager mode?

(48:17) Chase impact, not optics

(57:00) The 3 types of product leaders

(60:46) Aligning your environment, opinion, and superpower

(63:10) Shreyas’ non-consensus view on building product

(67:52) Mastering founder mode as a PM

(72:58) Getting in touch with Shreyas

(74:49) How to find Nikhyl

Not all successful companies can supercharge your career. And not all companies that struggle are bad for your career. How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture. Whether you're job hunting or evaluating your current role, these insights will help you identify environments that truly foster career growth.

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We also discuss:

• Strong signals of a supercharged company
• Why shipping velocity is crucial
• Learning opportunities at immature companies
• Looking for companies with strong talent
• What makes an excellent development culture

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Referenced:

• Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=913s
• Greatest hits on career advice with Peter Yang: https://www.youtube.com/watch?v=-BcCHEXAVVk
• Is my next job at a startup or big tech?: https://www.youtube.com/watch?v=MiELOo4_XGg&t=9s
• Should I join or leave an ex-hypergrowth company: https://www.youtube.com/watch?v=5-rr1cYYfEU
• Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-c
• Stage of Company: A career unlock: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s

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Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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, Twitter or email me at: nikhyl@skip.community

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Timestamps

(00:00) Episode Teaser: How to 10x your career

(01:10) Introducing the framework

(03:41) The caller’s question

(05:00) 1: Speed and execution

(08:43) 2: Market position

(11:47) 3: Quality of talent

(15:27) 4: Development culture

(20:22) How to get in touch

In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior role post-maternity leave, or seek opportunities elsewhere.

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We also discuss:

• Maximizing career potential without sacrificing family
• Reframing career decisions in the context of long-term growth
• How to have it all, just not at once
• The value of wartime leadership experience
• Overcoming job search anxiety

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Referenced:

• Avoiding burnout for high achievers

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Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

–

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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, Twitter or email me at: nikhyl@skip.community

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Timestamps

(00:07) Applying my career framework to the caller’s case

(02:13) Caller context

(02:52) Why one option is a “no-brainer”

(03:58) The value of wartime leadership experience

(07:43) Why you won’t regret choosing family > career

(09:53) The wisdom in “playing it safe”

(11:11) Key takeaways

(11:44) How to get in touch