Lenny's Podcast

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

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. Find the full transcript here: https://www.podpage.com/lennys-podcast/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/#transcript — 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 — Where to find Casey Winters: • Twitter: https://twitter.com/onecaseman • LinkedIn: https://www.linkedin.com/in/caseywinters/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: [00:00] What to expect in this episode with Casey Winters [03:23] An overview of Casey’s career [06:21] A look into the most-fulfilling and challenging roles Casey has energized [06:53] Communicating upward [11:21] How to derisk meetings [13:56] Are you properly preparing for your meetings? [19:12] Striving for perceived simplicity [24:25] Justifying non-sexy product improvements [27:50] Protecting what you’ve built vs continuously scaling [31:06] The downfall of functional ops roles [35:24] The CPO role: what it is and how to get there [40:47] The spectrum of product people [45:14] How to level up your skills [47:04] New growth trends, tactics, and strategies [50:35] Casey’s two stages of growth: kindle strategies and fire strategies [51:54] Under appreciated growth strategies [54:05] Where to find Casey

Casey WintersguestLenny Rachitskyhost

Jul 20, 202255mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Casey Winters on selling ideas, leading products, and unlocking growth

Casey Winters, CPO at Eventbrite and veteran growth/product leader, shares how to effectively communicate with executives, make strategic trade-offs, and keep products simple while expanding their power. He explains why non-sexy investments like performance and developer velocity are critical, how to structure and prepare for high‑stakes meetings, and what it really means to operate as a CPO. Casey also outlines a spectrum of product managers from idea-heavy innovators to execution machines and how to grow them into strategic leaders. Finally, he dives into modern growth strategy: when to hire for growth, building loops early, product-led sales, and the rising importance of data network effects.

IDEAS WORTH REMEMBERING

5 ideas

Treat executive communication as storytelling that starts at the right chapter.

When presenting up, don’t jump into the weeds (“chapter six”) or re-explain basics from the beginning of time; start at the last point you’re sure is obvious, ground in company strategy and key metrics, then build to your asks and conclusions.

Proactively escalate constraints and trade-offs instead of trying to be a hero.

Leaders can only evaluate outcomes fairly and help change circumstances if they know the real constraints; under-communicating upward leads to ‘out-of-touch’ execs and misaligned expectations.

Over-prepare for critical meetings by anticipating every plausible question.

High-leverage reviews (e.g., with CEO/CFO/board) often hinge on a few early context questions; great PMs pre-brief stakeholders, simulate the room, and ensure they have data and reasoning for likely lines of inquiry.

Aim for perceived simplicity: powerful products that feel simple to most users.

Hide advanced features until users seek them out or are ready, so complex capabilities don’t burden novices but remain discoverable for sophisticated users—WhatsApp and parts of Eventbrite’s marketing tools are examples.

Non-sexy work (performance, UX, dev velocity) is essential to preserve product-market fit.

As expectations and competition rise, ignoring foundational improvements erodes PMF over time; PMs must build custom metrics, small tests, and cross-functional alignment to justify and prioritize this work.

WORDS WORTH SAVING

5 quotes

If you're not an executive, whatever you're working on, you're basically writing and telling a story, and when you talk to an exec about that story, you have to start with chapter one.

— Casey Winters

The goal of your kindle strategies, these non-scalable hacks, they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users.

— Casey Winters

Users flock to a simple product. The product takes users for granted and adds more features for power users, and then users flock to the next simple product as a result.

— Casey Winters (referencing Scott Belsky’s concept)

Having marketing ops means you suck at marketing.

— Casey Winters

You're expected in this role to optimize for the entire company even at the expense of what's good for your team.

— Casey Winters on being a CPO

Upward communication and how to present to executives effectivelyManaging trade-offs and explaining non-sexy product investments (UX, performance, dev velocity)Designing for perceived simplicity while adding complex functionalityThe CPO role: scope, responsibilities, and path to get thereThe spectrum of PMs (innovators vs executors) and developing strategic skillsModern growth strategy: kindle vs fire strategies, when to hire growth, product-led salesData network effects and embedding growth loops into products early

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