Lenny's Podcast: Product | Career | Growth

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

July 21, 2022

AI Summary

5 min read

Casey Winters, growth leader at Eventbrite and formerly at Pinterest, shares frameworks for pitching ideas internally and advancing careers in product and growth roles. Drawing from his experience leading teams at scale, he emphasizes psychology-driven tactics for gaining buy-in without authority.

Psychology of Internal Selling

Winters explains that selling ideas hinges on addressing decision-makers' mental models and fears. People resist change due to loss aversion—fearing demotion or failure more than missing gains—so frame pitches around risk reduction and small wins. He stresses empathy: map stakeholders' incentives, like a CEO prioritizing revenue over efficiency, and tailor language to their worldview. Example: At Pinterest, he reframed growth experiments as "low-risk tests" to counter engineering's stability concerns.

Building Credibility Without Formal Power

Early career advancement relies on "competence signals" like shipping small features that demonstrate impact. Winters advises seeking "sponsors" over mentors—executives who advocate for you publicly—by delivering outsized results on their priorities first. He shares how at Eventbrite, he rose by owning metrics end-to-end, making his contributions undeniable. Caveat: This works best in data-driven cultures; in politics-heavy orgs, track alliances explicitly.

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What you'll learn

1 (00:00) **🎙️ Introduction: No Guest Featured**
2 (02:15) **Recent Market Volatility**
3 (08:30) **Fed Policy Outlook**
4 (15:45) **AI Investment Boom**
5 (24:20) **Crypto Market Update**
6 (32:10) **Earnings Season Highlights**

+ Full timestamped outline available in the app

Show Notes

The people who rise fastest in product know how to sell their ideas to customers, and also to their coworkers. Casey Winters, the Chief Product Officer at Eventbrite (previously at Grubhub, Pinterest, and advisor to dozens of companies) shares what it takes to be successful as you rise in the ranks within product. In this episode we’ll talk about how to land presentations, how to win over executives with strategic communication, the skill sets that are most in demand in product, and new growth trends. Join us.

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Thank you to our wonderful sponsors for making this episode possible:

• Coda: http://coda.io/lenny

• Mixpanel: https://mixpanel.com/startups

• Whimsical: https://whimsical.com/lenny

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Where to find Casey Winters:

• Twitter: https://twitter.com/onecaseman

• LinkedIn: https://www.linkedin.com/in/caseywinters/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, learn:

[00:00] What to expect in this episode with Casey Winters

[03:23] An overview of Casey’s career

[06:18] A look into the most-fulfilling and challenging roles Casey has energized

[06:50] Communicating upward

[11:18] How to derisk meetings

[13:53] Are you properly preparing for your meetings?

[19:09] Striving for perceived simplicity

[24:22] Justifying non-sexy product improvements

[27:47] Protecting what you’ve built vs continuously scaling

[31:03] The downfall of functional ops roles

[35:21] The CPO role: what it is and how to get there

[40:44] The spectrum of product people

[45:11] How to level up your skills

[47:01] New growth trends, tactics, and strategies

[50:32] Casey’s two stages of growth: kindle strategies and fire strategies

[51:51] Under appreciated growth strategies

[54:02] Where to find Casey

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