Leaving Stability Late-Career for AI Risk

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• Why your product intuition is outdated — and how to “go back to school” without quitting your job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 nikhyl@skip.community

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