44: Casey Winters - Thinking about your career like a long term investor.
Nov 20, 2023
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Former CPO of Eventbrite, Casey Winters, shares insights on career transitions, organizational alignment, and the future of technology. Topics include: dealing with misalignment, the impact of company strategy, taking care of OKRs, planning the return to work, technology and distribution changes, and the future of advertising and SEO.
Smooth transitions and avoiding bridges can lead to positive references and future opportunities.
Open and transparent communication is vital to address misalignment and foster a cohesive work environment.
Observing and learning before making high conviction bets on specific AI companies can lead to stable career opportunities.
Deep dives
Transitioning Careers and Importance of Smooth Exits
When leaving a company, it is crucial to prioritize a smooth transition and avoid burning bridges. Senior-level employees should give ample notice and ensure the transition plan is successful. Taking the time to coach junior employees on proper exit procedures benefits both parties and fosters positive references in the future.
Understanding Strategic Alignment within a Company
Misalignment among leaders within a company can cause significant stress and hinder progress. Ensuring that all executives and teams are aligned on goals and strategies is essential for a smooth operation. Having open and transparent communication helps address misalignment and fosters a more cohesive work environment.
Navigating Career Options in the Era of AI
As AI technology rapidly advances, individuals may feel overwhelmed or uncertain about their career options. It is important to understand that new distribution platforms for AI are still in the early stages of development. Thus, it is prudent to observe and learn before making high conviction bets on specific AI companies. Established companies integrating AI into their existing models may offer more stable career opportunities in the short term.
Building Bridges and Leaving Well
Leaving a job in a way that is respectful and beneficial for the company can lead to positive references and future opportunities. Taking the time to transition properly, ensuring a smooth handover and showing care for the company's success on the way out can leave a lasting positive impression. This approach can help maintain strong networks and open doors for advisory roles or new job opportunities. By being transparent and considerate when leaving, it is possible to avoid burning bridges and leave a lasting positive impact.
Transitioning and Prioritizing Personal Well-being
After leaving a all-consuming full-time position, it is important to take time for personal well-being. Focusing on physical and mental health can be a primary goal during this period. Maintaining a balance between leisure activities and personal growth goals is essential. Recognizing one's best hours of productivity and structuring the day accordingly can enhance productivity and satisfaction. It is crucial to avoid pushing oneself too hard to be productive and instead focus on accomplishing specific goals effectively.
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. 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.
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