Taking VP roles at struggling companies

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:

• 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

(00:58) 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.com