In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding her own company. While the search itself continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways. All three reported feeling something I’ve started calling smiling exhaustion: working hard, going long, and surprised by how good it feels. If you're a senior leader, sitting in a stable role debating a move, weighing how you can ride the AI shift, or quietly wondering if founding finally belongs on your career path, this conversation is for you.

Key topics:

• How AI agents have flipped the first year at a new role from headwind to tailwind, and are even bringing joy to the first year of a new role

• The new founding math: fast, fun, and skill-additive, with a much lower downside than it used to be

• How to navigate the job search when you don’t live in San Francisco—and remote jobs are dwindling

• Why structured AI learning is the wrong move, and what to build instead, so your fluency is hard to fake

• How to signal hard boundaries to a new boss, and differentiate between real respect and performative virtue-signalling

• Why holding your professional identity loosely matters when the role of senior leader is getting reformatted in real time

Referenced:

• Airbnb: https://www.airbnb.com/

• Atlassian: https://www.atlassian.com

• Claude Code: https://claude.com/product/claude-code

• Harvey: https://www.harvey.ai

10 Job-Search Rules That Just Broke

The Skip Podcast

10 Job-Search Rules That Just Broke