About this episode

This episode discusses the evolving landscape of job searching and career transitions for senior leaders with insights from three experienced guests.

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continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways.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…

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