Casey Winters
Casey Winters is a longtime and legendary advisor and operator. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit and until recently was the Chief Product Officer at Eventbrite, where he managed the PM, design, research, and growth marketing teams. Before Eventbrite, he led growth and product teams at Pinterest and Grubhub.
Career (separate track) Skills
Succeeding at the executive level requires recognizing that leadership is fundamentally about managing cross-functional trade-offs and the diverse communication styles of other stakeholders.
"Something I commonly say is that executive communication is actually executives communication. You're communicating with individual executives that all have different styles and different concerns abo..."
Growth & Retention Skills
Non-scalable growth tactics are temporary tools meant to ignite long-term, scalable product loops rather than ends in themselves.
"The goal of your Kindle strategies, these like non-scalable hacks, they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users."
Operating Cadence & Communication Skills
Effective executive communication requires framing your work as a narrative that explicitly connects project assumptions to high-level company strategy.
"One of the ways I try to frame it to my team is if you're not an executive, whatever you're working on, you're basically writing and telling a story. And when you talk to an exec about that story, you..."
Team & Organization Skills
Managers can upskill their teams by shifting focus from climactic presentations to proactive alignment and pre-meeting preparation.
"I think the best way to coach is actually to do it before the meeting, so I think there's a tendency in product management and product design to want to do meetings where there's kind of this big reve..."