44: Casey Winters - Thinking about your leadership career like a long term investor

Why you shouldn't burn bridges when it's time to go and when to enter the market again.

Nov 20, 2023

A Journey I’m in the middle of as well: How to transition from senior leadership to taking care of yourself to the moment where you enter again. Casey Winters, ex-CPO Eventbrite, walks through the entire journey and how he thinks about our current markets; our technology is drastically changing while the new distribution channels have not developed yet.

How it feels to write a strategy that you’re not part of but have to see it through.
How to not burn bridges on your way out
Why he is waiting before making high-conviction bets for his career in 2023

Timestamps:

08:10 Why Casey is stressed out and scared of misalignment

13:40 When the company heads in a direction where you don’t see your strengths as a senior leader, but it’s your job to see them through

20:12 This company strategy looks like one I’m not part of. How open should I be with my CEO?

28:00 Burning bridges on your way out by overthinking about negotiation leverage

31:15 Shifting your day to suddenly taking care of your OKRs: physical health and fitness

38:15 What deserves the best hours of your day?

42:00 How to plan the inevitable return to work: Waiting for the right moment, how to think like an investor about your career.

48:10 You don’t have to “understand” everything. But you’ll know when you know enough: technology is changing now, and distribution will change later.

53:40 Paid advertising and, with it, SEO getting pressure because of the current technology shift. Do consumer platforms make money from advertising or subscriptions in the future? It will be WILD.

62:20 Short tenures: people want to understand the decisions you made in your career, not just how long they were.