Lenny's Podcast: Product | Career | Growth
00:03:52 · Lenny Rachitsky, Casey Winters
[00:03:52] S1: Well, you're both worthy, and I'm honored as well. So thanks for joining me again. I have a lot of stuff that I wanna chat about. But first of all, I'm just curious. What are you up to these days? I know you left Eventbrite as CPO. I know you're doing a few adviserships with startups, but how are you spending your days, and what do you think is next for for Casey Winters? [00:04:09] S0: So I'm still still spending some time with Whatnot and Eventbrite as it... As advisers. Know, I stepped back from the CPO of Eventbrite in October, but still working on some long term marketplace strategy stuff, some growth strategy stuff. I'm on the board of a company called Beak, which is like Netflix for audio in Latin America. And I'm doing some angel investing in in marketplaces and in what I call tech debt as a service, which is, you know, what are startups that are building out things that were hard for my teams in the past to, like, build or maintain inside previous companies. The other thing I'm working on is revamping the product strategy program for Reforge. [00:04:48] S1: So I [00:04:49] S0: got some things keeping me busy, but but definitely not as busy as I was last year. [00:04:53] S1: This is like a rare, free agent Casey Winters time. Should people reach out if they're interested in maybe working with you? What's your advice for people listening and like...
00:04:53 · Lenny Rachitsky, Casey Winters
[00:04:53] S1: This is like a rare, free agent Casey Winters time. Should people reach out if they're interested in maybe working with you? What's your advice for people listening and like... [00:05:00] S0: Yeah. Look, I always love seeing how I can help companies. Right? So everyone should on the side reaching out and seeing if I have time to help, if there's something they think I can help with. I just... You know, I love talking to startups. So, yeah, absolutely. Like, can't can't promise anything, but, yeah, I I just love talking to people about this stuff. [00:05:18] S1: Awesome. And we'll point people to how to get in touch with you at the end of the episode, and it'll be in the show notes too. But talking about the CPO role, you're at Eventbrite, your CPO, it reminded me of a post you wrote about how hard the CPO role is, and there's some quotes that I recall in your post about how one... If you ever ask a CPO, chief product officer, how they're doing, no one's ever gonna say, I'm I'm crushing it right now. [00:05:40] S0: Yeah. [00:05:41] S1: And then there's this other quote about how you basically, as a spiel, just try to put some points on the board before you inevitably get fired. Why is that? Why do you find that? And do you still believe that to be true after, you know, leaving that role?
00:05:53 · Casey Winters
[00:05:53] S0: Yeah. I would say I still believe those things I said. It was funny. A product leader who will remain nameless emailed me when I hit year three at Eventbrite, and they said, congrats. You didn't get fired after two years. What's your secret? You know, I I think it's very hard to keep product market fit as a CPO within a company for a long time. You know, the needs of the business shift over time. And, course, we all have different strengths and weaknesses in our game. Like, no one's perfect at everything. And in general, you know, as an executive, it's just impossible to do everything perfectly. And any little misstep, mistake, or something you just miss can blow up in a major way. You know, frequently, CEOs have visions that can change and get misaligned with with the product leader. And also, you know, with leadership roles, you don't get put on a pip. Right? Like, if a CEO loses confidence, it's over immediately. So nothing like that happened at Eventbrite. I started to see that the areas of leverage for a product leader were just less in my wheelhouse over time. And I just talked to my boss about it and, you know, worked out something where I continue to advise on the things that, you know, I'm uniquely good at and and find other people who are better at some of these other things that were maybe more important at the time. But, yeah, it's it's a really hard role, a really, challenging role. You know, it can be a lot of fun, and I I, you know, I learned a lot from doing it. But, yeah, I still believe, and I think I've still yet to hear someone say they've really crushed it.
00:07:25 · Lenny Rachitsky
[00:07:25] S1: Is there anything that you learned from that experience to to survive in that role for three years? You know, I imagine you have a lot of skills and you're very valuable to the company, but I don't know. Any... Someone that's in that role, maybe right now, just like, here's something that I did that maybe you should do.
00:07:40 · Casey Winters
[00:07:40] S0: The first one I can think of is a big change from being a product leader to a, you know, a CPO or or something equivalent is you're actually a comp exec first and a product exec second. So I think some mistakes I made, you know, early that I I corrected successfully is you wanna show that you are caring and paying attention to the overall business first before just taking care of your own, you know, product designers, product managers, researchers, whoever. So that's that's advice I found myself doling out to other product leaders a lot more now that have, you know, gone through it. You have to not only truly care, but create the perception that you care about sales, about marketing, about, you know, legal, etcetera. Because first and foremost, you're expected to leave the business, you know, at at that level. So I think that's something that I think is really important, and I think something else is really trying to diagnose without as much bias as possible where the strengths and weaknesses of your team, where the strengths and weaknesses of your product, lay that out with your peers and say, here's where we are, here's where I think we need to go, here's the timeline on which I'm gonna work to get us there. Because I think product's such a confusing, discipline for people who aren't in it, a sales leader, many CEOs, you know, marketing leader, that they don't necessarily know what great looks like. And the things they know about great leadership, they don't know if you know those things. So you have to make it really clear. Yeah. I know our OKRs are not as quantitative as they should be yet. That's because this team isn't ready for x, y, and z. This is where we're gonna get them to, but it's gonna take some time. So one of the things we did at Eventbrite that I thought was really helpful is, you know, when you go public, you tend to rotate over your executive team and get public company execs versus startup execs. So a few of us were new, and it's just like, hey. Let's do a deep dive on product. Let's do a deep dive on customer support. Where is it at right now? What do you feel like your job is? What do you feel like are the issues you're facing? Where do you wanna take it over the next three to five years? And then let's talk about it.
00:09:55 · Casey Winters, Lenny Rachitsky
And just forcing you to, like, write it all down is is really helpful, but then it forces you to explain it. And it helps the rest of the executive team get better company execs because, you know, now they really understand product a lot more deeply or understand finance a lot more deeply, whatever the function is. [00:10:15] S1: Speaking of, gaps and opportunities for people in the company to level up, you've kind of been, highlighting this trend that I thought was really interesting, something you call the zero interest rate phenomenon product manager. Can you talk about what that is and what you've been noticing?