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:

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

(00:46) 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]

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:

• 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

(00:53) 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]

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:

• 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

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]

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:

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

–

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

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.

–

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:

LinkedIn

She Leads Podcast

Twitter/X

–

Where to find Nikhyl:

Twitter/X

LinkedIn

–

Find The Skip:

Website

Substack

YouTube

Spotify

Apple Podcasts

–

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

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:

• LinkedIn
• She Leads Podcast
• Twitter/X

–

Where to find Nikhyl:

• Twitter/X
• LinkedIn

–

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts

–

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

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.

–

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:

• LinkedIn
• She Leads Podcast
• Twitter/X

–

Where to find Nikhyl:

• Twitter/X
• LinkedIn

–

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts

–

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

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:

• Tech compensation: Beyond the offer letter

–

Where to find Carly:

• LinkedIn
• She Leads Podcast
• Twitter/X

–

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 [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

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.

-

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

-

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/

-

Where to find Carly:

• LinkedIn
• She Leads Podcast
• Twitter/X

-

Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

-

Where to 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.

-

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 [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