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Casey Winters

2 episodes

Episodes

Why most product managers are unprepared for the demands of a real startup | Casey Winters

Apr 14, 20231m

Guest: Casey Winters - Chief Product Officer at Eventbrite. Casey has extensive experience advising and working with top consumer companies on product and growth strategies, including Pinterest, Airbnb, and GrubHub. Key Takeaways: Communication is Key: Effective upward communication involves starting with the company strategy and assumptions before diving into specifics. Role-playing and pre-meetings can help prepare for executive questions. Balancing Simplicity and Complexity: Eventbrite aims for "perceived simplicity," where advanced features are discoverable but don't complicate the user experience for those who don't need them. Justifying Non-Sexy Investments: Align with peer leaders to prioritize essential but less glamorous projects like performance and stability improvements. Demonstrating potential future risks can help justify these investments. Product Management Spectrum: PMs range from idea generators to execution-focused individuals. Moving towards the middle, where strategy meets execution, is crucial for career advancement. Growth Strategies: Early-stage companies should focus on "kindle strategies" to unlock scalable "fire strategies." Consider product-led sales for B2B growth and build growth loops into the product early. Topics Covered: Product management communication, balancing product complexity, justifying infrastructure investments, product management spectrum, growth strategies, product-led sales, data network effects.

How to sell your ideas and rise within your company | Casey Winters, Eventbrite

Jul 21, 202255m

Guest: Casey Winters - Former Chief Product Officer at Eventbrite. Casey is a renowned figure in the growth and product community, having advised and worked with top companies like Pinterest, Reddit, Canva, and Airbnb. Key Takeaways: Frameworks as Tools: Frameworks should be seen as tools to be used when relevant, not as rigid processes that stifle creativity and risk-taking. Founder Intuition vs. Team Expertise: Founders should direct until team members demonstrate they can make better decisions, but employees should signal when they are ready to take over. Network Effects: Understand the different types of network effects (direct, cross-side, data) and how they can evolve over time to strengthen a business. Consumer Subscription Challenges: Consumer subscription models lack the net dollar retention of B2B SaaS, making them harder to sustain without network effects or unique growth loops. Marketplace Dynamics: Grubhub's disruption by DoorDash highlights the importance of reacting to market changes and the potential need to overreact to existential threats. Topics Covered: Product management frameworks, founder intuition vs. team expertise, network effects, consumer subscription challenges, marketplace dynamics, Grubhub vs. DoorDash case study.

Notable Quotes

โ€œPeople just way under communicate upward inside of companies.โ€

Communication in organizations

โ€œIf you got a product that retains well and you can't find more users for it, I don't think that's product market fit.โ€

Product market fit

โ€œData network effects are underrated.โ€

Growth strategies

โ€œIt's very hard to keep product-market fit as a CPO within a company for a long time.โ€

CPO challenges

โ€œYou want to show that you are caring and paying attention to the overall business first before just taking care of your own product designers, product managers, researchers.โ€

CPO advice