How to sell your ideas and rise within your company

Casey Winters, Chief Product Officer at Eventbrite and a longtime growth advisor who has worked with Pinterest, Airbnb, GrubHub, Tinder and others, discusses his path from marketing analyst to CPO. The conversation covers executive communication and trade-offs, keeping complex products simple, justifying unglamorous product investments, the product manager talent spectrum, and modern growth strategy.

01Key learnings

• Escalate problems to leadership early so they can help change circumstances, rather than silently absorbing them; leaders can't evaluate fairly what they don't know.
• Structure upward communication to start at the last point the audience already agrees with, not at the chapter-six detail or with a re-explanation of company strategy.
• Prepare for important meetings by role-playing each attendee and listing every possible question, ensuring you have the data to answer them before the meeting.
• Pre-meet key stakeholders individually so they aren't surprised and any concerns surface before the big presentation.
• Keep products simple with perceived simplicity: advanced features exist but are only discoverable when users go looking, so the default experience stays clean.
• To fund hard-to-measure work like performance or developer velocity, build custom metrics, run small tests, and first align a few peer leaders behind it.
• Protect existing gains at scale: product-market fit erodes as user expectations and competition rise, so continual improvement is required to keep it.
• Treat operations roles as a signal of inefficiency; the goal of ops should be to automate or eliminate the manual work so the role is no longer needed.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.