S4 Ep.03 Casey Winters - Design, Growth & Evolution of Product Organizations

Boundaryless Conversations Podcast

Casey Winters is a growth advisor and operator who helps companies scale. Casey is a legend of product growth and marketplaces, and, among many other things, he’s an advisor and operator that helps companies address the problem of scale. Most recently, Casey was the Chief Product Officer at Eventbrite. Before that, he had extensive experience working for and advising companies such as Grubhub, Pinterest, Airbnb, Canva, Thumbtack, Reddit, Hipcamp, Faire, and many others. Casey is also a partner at Reforge, one of the leading growth programs available.

Besides sharing real-world experiences from his career, in this episode, Casey provides insights about how companies can leverage their organizational model as a growth lever. Casey explains how the growth model is a unique aspect of each company and highlights the importance of reducing friction to allow growth to flow more strongly. We also discuss how the responsibility for driving network effects often shifts from local teams to more centralized functions over time, and how leaders should think about autonomy when managing growth and product teams.

Remember that you can always find transcripts and key highlights of the episode on our website: https://boundaryless.io/podcast/casey-winters/

Key Highlights of the Conversation
👉 The organizational structure can change according to strategy, especially at the early stage of a business.
👉 Growth model: what it is and the structures you need around it.
👉 OKRs and creative spaces: how should a leader balance these in a team?
👉 How can marketing and growth teams work together?
👉 Brand vs. performance: how a startup should think about it.

To find out more about Casey’s work:
👉 Twitter: https://twitter.com/onecaseman
👉 Website: https://caseyaccidental.com/
👉 LinkedIn: https://www.linkedin.com/in/caseywinters/

Other References and Mentions:
👉 The Types of Product Team Organizational Structures | Casey Accidental: https://caseyaccidental.com/product-organizational-structures/
👉 Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law
👉 The Autonomy Spectrum: https://caseyaccidental.com/the-autonomy-spectrum
👉 Dynamic creative optimization: https://en.wikipedia.org/wiki/Dynamic_creative_optimization
👉 Reforge teaching: https://www.reforge.com/advanced-growth-strategy-series

Casey’s Suggested Breadcrumbs (Things Listeners Should Check Out):
👉 Severant - Kuedo: https://kuedo.bandcamp.com/album/severant-2022-edition
👉 Infinite Window - Kuedo: https://kuedo.bandcamp.com/album/infinite-window

Recorded on 17 October 2022.

Get in Touch with Boundaryless:
Find out more about the show and the research at Boundaryless at https://boundaryless.io/resources/podcast/
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👉 Website: https://boundaryless.io/contacts/
👉 LinkedIn: https://www.linkedin.com/company/boundaryless-pdt-3eo/

Music
Music from Liosound / Walter Mobilio. Find his portfolio here: https://blss.io/Podcast-Music