Seeding AI capability across the org

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

• Twitter/X

• LinkedIn

Where to find Anneka

• LinkedIn

Where to find Dheerja

• LinkedIn

Where to find Yuhki

• LinkedIn

Join The Skip

• Skip Coach

• Skip Community

Find The Skip

• Website

• Substack

• YouTube

• Spotify

• Apple Podcasts

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 nikhyl@skip.community

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