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

1. 0:00 – 3:23

   What to expect in this episode with Casey Winters

   1. CWCasey Winters0:00

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

   2. LRLenny Rachitsky0:08

      (instrumental music) Pinterest, Airbnb, Tinder, Reddit, Canva, Hipcamp, Faire, Eventbrite. What do these companies all have in common? I'll tell you. Casey Winters. As far as I know, Casey has worked with and advised more consumer companies on their product and growth strategies than anyone in the world. He's also really generous with his time and sets time aside to help founders and product leaders. I always learn so much talking to Casey, and I'm really excited for you to hear this episode. In our chat, we cover Casey's advice on making trade-offs as a product leader, justifying non-sexy product improvements, the spectrum of product people and how to level up your skills to wherever you are on that spectrum, new growth trends and tactics and strategies that he's seeing, when to focus on growth, and his top advice on growth strategy and a bunch of other stuff. As a big bonus, we're actually gonna be doing a live AMA with Casey in my newsletter Slack community. It's gonna be on August 5th at 10:00 AM Pacific Time. And so, if you'd like to ask Casey any questions, make sure to get into the Slack. Until then, enjoy this episode with Casey Winters. Hey, Casey Winters. What do you love about Coda?

   3. CWCasey Winters1:23

      Coda is a company that's actually near and dear to my heart because I got to work on their launch when I was at Greylock. But in terms of what I love about it, you know I love loops. And Coda has some of the coolest and most useful content loops I've seen. How the loop works is someone can create a Coda and share it publicly for the world. This can be how you create OKRs, run annual planning, build your own map, whatever. Every one of those Codas can then be easily copied and adapted to your organization without knowing who originally even wrote it. So they're embedding the sharing of best practices of scaling companies into their core product and growth loops, which is something I'm personally passionate about.

   4. LRLenny Rachitsky1:59

      I actually use Coda myself every day. It's kind of the center of my writing and podcasting operation. I use it for first drafts, to organize my content calendar, to plan each podcast episode, and so many more things. Coda is giving listeners of this podcast $1,000 in free credit off their first statement. Just go to coda.io/lenny. That's coda.io/lenny. This episode is brought to you by Mixpanel, offering powerful self-serve product analytics. Something we talk a lot about on the show is how startups can build successful and amazing products. And relying on gut feeling is a really expensive way to find out if you're heading in the right direction, especially when you're raising money, because VCs don't want to pay the price for these kinds of mistakes. That's why Mixpanel will give you $50,000 in credits when you join their startup program. With Mixpanel, startups find product market fit faster, helping you take your company from minimal viable product to the next unicorn. Access real-time insights with the help of their pre-built templates and know that at every stage, Mixpanel is helping you build with confidence and curiosity for free. Apply for the startup program today to claim your $50,000 in credits at mixpanel.com/startups, with an S. And even if you're not a startup, Mixpanel has pricing plans for teams of every size. Grow your

2. 3:23 – 6:21

   An overview of Casey’s career

   1. LRLenny Rachitsky3:23

      business like you've always imagined with Mixpanel. Casey, welcome to the pod. I feel like every time that we chat, I leave with at least one new perspective that kind of bl- blew my mind on product or growth or even just the world. And so, I'm really excited to have this conversation, mostly to s- selfishly extract as much knowledge out of your head as I can in the hour that we have together. And so, with that, welcome.

   2. CWCasey Winters3:53

      Very kind. Happy to be here.

   3. LRLenny Rachitsky3:55

      So, you've worked at so many iconic companies and worked with so many iconic companies. It almost boggles the mind just looking at your LinkedIn, trying to scroll through LinkedIn and have to click on, like, see additional experiences and all. And there's just so many places you've worked, so many companies you've worked with. Could you just give listeners maybe a 10,000-foot view of your career arc through product

   4. CWCasey Winters4:18

      Well, I started my career as an analyst at Apartments.com on the marketing side. So, it was my job to measure every channel for effectiveness in driving leads. These are things like, you know, SEO, AdWords, affiliate marketing, email. So, once I got good at measuring that, I naturally started working on optimizing those channels directly, and then I started, you know, going to do re- user research and understand how the product could be better so that we could convert leads better and... It was at that point that I got the feedback from the company that I was this weird marketing and product hybrid and they didn't really know what to do with that, 'cause those were two totally separate departments. It wasn't until I got to Grubhub and I was the 15th employee and they were like, "Dude, we don't care." Like, "As long as you grow how many people order food, I don't care if you work on marketing, I don't care if you change the product. Do whatever will have results." And we now call these roles growth, but, you know, that term didn't exist at the time. So, I basically worked on growing the demand side of that business from Series A to IPO. We ended up creating a product management function out of my team there, but for the first four years, we didn't have product titles either. That, you know, that was kind of a newer idea also. It wasn't until I went to Pinterest that I was actually formally labeled a product person. I ended up leading the growth product team there. We basically had to rebuild the growth model of, of the business to, to reignite, uh, growth. So, I was there from 40 million MAU to 150 million MAU. And it was around that time that I started doing some more advising, you know, with, with Airbnb on the demand side, with Pocket, and then I went to a VC named Greylock Partners and worked with their companies on, on growth and scaling.... and then I just independently started working as a full-time advisor with companies like, you know, Eventbrite, Tinder, Thumbtack, Canva. And after doing that for a couple of years, Eventbrite opened this chief product officer role, and they asked me to take it. So now I've been doing that for three

3. 6:21 – 6:53

   A look into the most-fulfilling and challenging roles Casey has energized

   1. CWCasey Winters6:21

      years now.

   2. LRLenny Rachitsky6:21

      That's an excellent segue to our next little segment that I want to get into, which is, uh, partly your CPO role and the work that you do there, and also touching a bit on a bit of the writing that you've done. So, you're currently chief product officer at Eventbrite, which is a company that I love. I have so many friends there, and they're all amazing. Uh, such a big fan of the company. And I know a lot of listeners are maybe thinking about becoming CPO someday as a goal. And so, I thought it'd be cool to chat through some of the challenges that you're having and some of the things you've learned in the role.

   3. CWCasey Winters6:52

      Sure.

4. 6:53 – 11:21

   Communicating upward

   1. CWCasey Winters6:53

   2. LRLenny Rachitsky6:53

      Cool.

   3. CWCasey Winters6:53

      Yeah.

   4. LRLenny Rachitsky6:54

      I'll be more specific. So, one of the things that you mentioned that you're working on is thinking about trade-offs and being very explicit about trade-offs you're making, communicating why you made certain trade-offs, and then just generally communicating that upward to executives and across the company, so I'm curious just to hear what you've learned around how to communicate trade-offs in internal communication.

   5. CWCasey Winters7:14

      Yeah. One of the things I found, especially during the pandemic at Eventbrite, where, you know, we weren't obviously hiring a lot of people, and we had, you know, lots of various issues come up, is that a lot of managers and leaders would just try to deal with issues on their own and not raise them, you know, or escalate them with, with me in particular. And some of these were, like, really tough situations. So then, you know, later on, I'd ask why something went wrong or why we didn't achieve a goal, and I'd get, you know, some feedback from my team of like, "Hey, you don't understand the situation. This is really impossible. There's all these things going wrong." And then I respond like, "Yeah, of, of course I don't understand the situation because you haven't told me about it." Like, how am I supposed to evaluate things fairly if you don't let me know what's really going on? So, you know, these people on my team thought that being a leader was, you know, handling it the best they could given the circumstances, when, you know, in many cases, the right way is to escalate the issue so that perhaps I can help them change the circumstances so the circumstances aren't as dire. And if I can't change the circumstances, I'm at least aware of the circumstances and the explicit trade-off we've made to deal with, you know, that situation, and then I can help communicate that better to others across the company, and I can help evaluate the results with the proper context and do it more fairly. So, I find that, in general, people just way undercommunicate upward inside of companies, and then they'll complain that executives are out of touch, you know, when they aren't telling executives what the executives need to know. So, you know, then when, you know, people inside a company do try to communicate, you know, upward, a lot of times they're so in the weeds that as, as an executive I just don't understand what they're saying, and then when I ask questions, it's like, as an exec, I'm asking a question in another language. It's like, uh, I don't know if you've ever seen Ocean's Twelve-

   6. LRLenny Rachitsky9:10

      Mm-hmm.

   7. CWCasey Winters9:10

      ... but as a joke they invite Matt Damon to this business meeting and they just talk in code as a prank on him, and, you know, that's what a lot of people on my team feel sometimes when they're talking to the executives, of like, "I don't even understand what these questions mean." Like, it's like you're speaking, you know, another language. So, one of the ways I- I try to frame it to my team is like if you're not an executive, you know, 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, which is, you know, what part of the company strategy are you working on? What metrics are you trying to improve? What assumptions are you making that are guiding, you know, what you're building? And I, and I find that many times when non-executives are presenting to execs, they'll start on, like, chapter six, so, you know, even if that part of the story is right, it's like a good story, you haven't earned the right to tell that part of the story yet because you skipped the first five chapters. Um, I- I've definitely seen people with the opposite problem as well, which I call, like, starting at the beginning of time, where, you know, you- you come into a meeting, you know, with the CEO or with the CFO or something, and you basically spend, like, the first, like, 20 minutes re-explaining the company strategy or who our customer is or something that everyone already knows, and then by the time you get to explaining new information, you've, you've used up, you know, your allotted time. So, I try to coach my team to be in the middle, right? Like, don't start on chapter six of the story, but also, like, don't start with a textbook on the English language either. You wanna, you wanna find the last point in your story that would be completely obvious to the person you're telling the story to and then go from there to things that would be less obvious but that they can follow along with. And, uh, it- it's, it's a lot of work to really dial that in across different types of people you're trying to communicate that story to, 'cause of course, upward communication isn't all that you're doing, right? You're trying to communicate that down to your team, to individual engineers and designers, and they're gonna need to hear some very different things than say, the CPO of the company or the CEO of the company. So, it's a challenge I see quite

5. 11:21 – 13:56

   How to derisk meetings

   1. CWCasey Winters11:21

      frequently.

   2. LRLenny Rachitsky11:22

      Can you talk a bit about how you actually coach PMs on this? Is this like in our one-on-ones you revisit a presentation they gave that could have been better? Is it at- after a presentation you pull them aside and talk through what they could have done better? How do you approach that?

   3. CWCasey Winters11:36

      Well, I think the best way to coach is actually to do it before the meeting. So, I think there's a tendency in product management and product design to want to do meetings where there's kind of this big reveal and an aha to the audience, and it's kind of the opposite of how you want to handle most of these situations. You want to de-risk that meeting, not, like, make it a, a big, you know, success or fail moment. So, there's a few things that I do. One is if there is a big, you know, presentation coming up or something like that-I try to run through it with the team, pretending to be the other members of the audience that are gonna be there. So, I'll say, "Okay. Well, what the CFO's going to ask about here is X and you want to answer that question before it gets asked. What Julia, our CEO, is gonna ask about is Y, so you wanna weave that into the early story and not, like, wait for her to ask." So, you kind of role play the entire thing based on the difference people that they're going to be communicating with. Uh, something that I commonly say is that executive communication is actually executives' communication. You're communicating with individual executives that all have different styles and different concerns about the business, or about the particular problem you're working on, and you want to anticipate that. And if you don't have enough experience, say, presenting to the CFO or the CEO, I, as the chief product officer, do. So I can, you know, impersonate them and help you understand what they're gonna, you know, care most about. The other thing that I push a lot of my team to do is have pre-meetings with some of those key individuals so that they're gonna be less surprised in the meeting about what you're talking about, that you've gotten any major concerns brought to your attention before, you know, the big meeting, and that helps, you know, de-risk, you know, how poorly a meeting like that can go. But- So, definitely at the individual presentation level, doing that pre-meeting. What I'm working on a lot now is trying to be- trying to have more of a scaled approach to training, you know, this type of upward communication and what types of frameworks, you know, what types of structure tend to work, you know, for Eventbrite? And making sure that everyone on my team is just really well versed in that a- and comfortable in it. Because, of course, confidence projection is a key part of- of these types of meetings as

6. 13:56 – 19:12

   Are you properly preparing for your meetings?

   1. CWCasey Winters13:56

      well.

   2. LRLenny Rachitsky13:57

      This is such important advice that I think a lot of PMs don't recognize how important it is to prepare for important meetings like this. Just to give folks context maybe that aren't doing this sort of thing when they're working at a larger company, how much time do you spend, or- or an ICPM should spend on preparing for these things? Just to set a little bit of a reference point.

   3. CWCasey Winters14:17

      Well, you know, it's an interesting question because I think different people have different styles on how they wanna handle this. I'd say the way my brain works in these situations, whi- which I think is a little bit atypical, is I'm actually a little bit better if I am free-forming a lot of elements and just speaking from confidence in areas I know, versus specifically trying to lay out every exact bullet point I wanna hit. I'm gonna show up as more comfortable, I'm gonna show up as more dynamic, and I'm gonna be able to engage in a more thoughtful conversation. So, for me, my approach to these sorts of things is I write a lot. I write a lot of notes, I write a lot of documents, and then in general, for any of these types of communications, I am just pulling from things I know deeply because I've written them down, I've thought- I've thought a lot about them. For a lot of other people, they really just need to spend a lot of time on prep to make sure they nail the communication they wa- they wanna nail. And I found it requires a different amount of investment for different people on my team. So, the- the point is not as much how much time you spend, it's how well do you really know the material? And how well do you really know what your audience is going to care about with that material so that you are prepared for every question you might get? So, I'll- I'll give an example from my Pinterest days. You know, the primary way which was- you interfaced, uh, on any, like, key strategic topic was product review, right? You'd go in and you'd talk to, you know, Ben, our CEO, and- and Jack, our- our head of product. And, you know, Ben and Jack had very different styles of communication. Jack, in particular, would very early on ask a few different data questions to get context on the problem. And if you, as a product leader, or an individual PM, or an individual designer, didn't know the answers to any of those, it casts doubt on the entire rest of that meeting because, you know, the team wouldn't be confident that you had all the right context to understand the problem. So, a lot of what I would coach my team on is, "Okay. I'm pretty confident Jack's gonna ask this question, then this question, then this question. Based on the material I'm seeing from you, how well are you prepared, you know, to answer those questions?" You know, different execs might be somewhat- somewhat different in that regard, but if you haven't thought through all the questions that might be asked from the document that you're sharing, or the presentation you're about to present, you're not prepared enough, right? Like, you need to know the entire universe of how that meeting can go, and that may take you dozens of hours. It might take you three hours. But the most important thing is that you've- you've asked, "What possible questions could be asked and am I prepared to answer all of those? Do I have all the data in front of me to answer all of those? Because if I don't, the chances of, like, the meeting, you know, having a- a- a negative outcome just increased dramatically."

   4. LRLenny Rachitsky17:21

      I imagine some people are listening to this and they're like, "Holy shit. I need to spend this much time on preparing for meetings like this." But in my experience, that's exactly what you do need to do to be successful, and so this is real good. Real talk about how long it takes to prepare for important meetings like- like the ones you're talking about.

   5. CWCasey Winters17:36

      Absolutely. I mean, you know, for better or worse, um, the way that a lot of key decisions are made inside companies are through these types of- of forums and meetings. And it's an extremely high leverage piece of time for a product manager or a product designer in terms of how much impact they can have. And if you are under-preparing for those sorts of things, the chances of you being able to have the type of impact you want, to have the type of career growth you want just go down dramatically. And I'm sure, you know, you and I have definitely made mistakes in our career in- in important meetings, you know, in the past, but I think, you know, one of the things that I really try to do is learn from each one of those and make sure those types of issues wouldn't happen again. And...Now, I feel like I have a pulse on... I know if I haven't done the work going into a meeting that's gonna make it have a more negative result, and now I'm pretty accurate, you know. And look, sometimes you just didn't have enough time and it is what it is. But now I know, like, "Okay. I know I'm not quite prepared for this and it can go, it can go poorly as a result." And I know also when I've done the right prep and I'm ready for anything, whether it's a board meeting, you know, you know, or a meeting with the executive team, or a meeting with an external partner, right? And I think that's what you're trying to build, you know, as any sort of product leader or PM or product designer or researcher, is that intuition of like, "I'm ready for this. I know everything that's gonna come at me. I'm prepared for any eventual outcome." And if you're not, then probably the answer is spend more time to get ready.

7. 19:12 – 24:25

   Striving for perceived simplicity

   1. CWCasey Winters19:12

   2. LRLenny Rachitsky19:12

      Speaking of spending more time, another topic that you shared with me that you're thinking about, thinking a lot about as a CPO is keeping the Eventbrite product simple-

   3. CWCasey Winters19:23

      Right.

   4. LRLenny Rachitsky19:23

      ... while adding more and more functionality to make it more usable by more people and more use cases. And so I'd love to hear how you're approaching that, because I know that's something every single product faces eventually, assuming they keep growing and surviving and keep adding more power.

   5. CWCasey Winters19:38

      Yeah. You know, Scott Belsky, who's the chief product officer of Adobe, he has this concept of the product life cycle y- you know, you're probably familiar with, but I'll explain it, you know, to your listeners, which is, you know, 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. And, you know, I've done a lot of, you know, research and, and, and work on this problem, and I found that there are a few different design hacks, essentially, that companies use to try to avoid this cycle, you know. One is, okay, if you build out more complex functionality, un-bundle it over time, like Facebook Messenger or Uber Eats have done, right? You know, at Pinterest, we were heavy, we did heavy investment in progressive disclosure, which is, you know, let's hide a lot of the more complex functionality until we make sure our users learn the really critical functionality, and then we can kind of open up more of the full suite of the product. Then there's just, you know, proactive training, right? Like, you can get on a video call with your customers or, you know, a phone call, much more common in enterprise, obviously. Or you might have a custom UI that goes away over time that's giving you the training wheels. Um, you can also segment experiences based on different user types. So, certain users might get a very simple user experience, and then some users might get the more complex one, and there's different packages and, you know, interfaces that cleanly separate the two. Maybe that more complex experience also bundles in, you know, training. So, what I found is that just none of these really work that well (laughs) for the Eventbrite, um, scenario, because we have different types of event creators across every possible level of complexity and sophistication. We have people that are putting on their first event and they expect five people to show up. We have, you know, people putting on 100 events per year that, like, really know what they're doing. And then users also shift from one of those categories to another over time. They can get more sophisticated as, as they build up their business. So segmentation doesn't really work that well. You know, progressive disclosure doesn't work that well either, because in many of these cases, we never want certain types of users to find the more advanced stuff. It's just gonna confuse them. So, we strive for this concept of what we call perceived simplicity, which is, there are advanced features in the product and they are easily discoverable when you look for them, but they're effectively hidden if you're not looking for them. And of course, the majority of users aren't gonna ever look for them. So, the advanced, more complex areas of the product don't make the product harder to use for the majority who will never need that level of complexity. And, you know, there are areas where we do this well and areas where we're still, you know, working on getting better, but that's really our aspiration. The company that I feel like has always done the best job of this is, is WhatsApp, where, you know, (laughs) at its core, it's a chat app and it's really good at being a chat app. But I remember when I went to Brazil, all of a sudden I started receiving, like, voice messages, and it was really easy to figure out how to use them and how to do them myself. When I needed to learn how to do video calls or phone calls, like, it would take, like, less than a second to figure out how to use the more advanced stuff. But it, it's effectively kind of hidden if you're not looking for it. That's, you know, what we aspire to at Eventbrite and, uh, you know, in some cases we're doing well, in some cases we definitely have some work to do.

   6. LRLenny Rachitsky23:02

      Is there an example of a win in that direction in the Eventbrite product that, that you're proud of using this model? Or even something that's like, "Oh man, this is really broken."

   7. CWCasey Winters23:11

      Yeah. Um, we've definitely had some wins here on the marketing side of our products. So one of the bigger investments we've made recently is, you know, our creators do a lot of their own marketing to try to get people to come to their events and, you know, transact on Eventbrite in the process. But our event creators, you know, they're not professional marketers, right? They're, they try to figure these tools out. So, we built a product that allows them to automate their, you know, Facebook advertising to get better results, you know, supercharged by our data. And the product's working really well. What we, we found is that there are certain segments that want to geek out on this a little bit, right? They want to figure out all the different target segments and, you know, optimize their creative. And then there are many, uh, creators who just kind of want it done for them. So we've been able to build some interfaces where the default is like super simple, we'll handle the targeting for you, we'll handle the creative. And then, hey, here's an on-ramp if you want to get a little bit more sophisticated and, and do more of this yourself. So that's an area where I wouldn't say we've, like, perfected it, but we've now really understood those different types of users and have easy paths for both of them to be successful. So I'm really happy with that.

8. 24:25 – 27:50

   Justifying non-sexy product improvements

   1. LRLenny Rachitsky24:25

      Awesome. Another topic that, that you wrote about that kind of touches on the stuff we were just talking about is, is justifying non-sexy product improvements, things like stability, performance, developer velocity, things that as a PM leader, you're just like, "No, no, no, let's just..." Us- the default is, "Let's do that later, we gotta hit our fricking metrics. We gotta drive growth." And you had some really interesting insights on how to, how you think about justifying these sorts of things, and so I'd love to hear that from you.

   2. CWCasey Winters24:53

      You know, the idea is that some of the most impactful projects that product teams can work on at scale, you know, not early stage startups per se, but at scale, are the hardest to measure. And because of that, they just get chronically underfunded. You know, it's that old adage, "What gets measured gets managed," right? So for things like user experience or performance or developer velocity or just a product area that's deemed unsexy like growth used to be back in the day, you know, I, I walked through some examples of a few tactics that work to get around this problem. Building custom metrics to show the value, being able to run small tests that prove the worthwhile-ness of the investment, creating some team principles that make sure you don't ever kind of forget about these important elements that can hurt you in the long run, and also just how to use experiments to build buy-in at the broader level. And, you know, one of the, the main takeaways besides some of those tactics in, in being successful here is that you have to get a team to buy-in to this. You can't really do a lot of this work alone, right? So if you're a PM, like, you want to be approaching this from a, "Well, my engineering manager and my design leader also bought in that we need to, you know, uh, work on performance," or, you know, "We've all aligned that the user experience is not going in quite the direction we want, and we want to, you know, head some problems off that may not, you know, improve metrics today but, you know, could certainly decline metrics, you know, tomorrow." And if you can get a s- like, a small team, you know, with two, three people aligned on the importance of something that's deemed unsexy, it's, it's a lot easier to start a... build this game plan around, you know, metrics or running small tests or, you know, structuring OKRs to not only prioritize this work, but to show some really massive impact and which could then get the rest of the company much more excited to make investments themselves.

   3. LRLenny Rachitsky26:51

      So what I'm hearing is step one is just get your kind of le- peer leaders aligned behind something that may not obviously be something your lead- your leaders, uh, want you to do. Is that right?

   4. CWCasey Winters27:02

      Absolutely. Yep.

   5. LRLenny Rachitsky27:03

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9. 27:50 – 31:06

   Protecting what you’ve built vs continuously scaling

   1. LRLenny Rachitsky27:50

      Is there anything else that you think is really valuable, powerful, effective in just getting folks to... getting your leaders to basically go along with something that maybe isn't gonna move metrics? Or is that the core of it?

   2. CWCasey Winters28:00

      Well, yeah, I mean, definitely it's hard when you can't create a metric that they can understand. I think the, the other area to think about is when, when you're an early stage company, everything you're doing is trying to drive upside, like, trying to drive growth in some way. It could be short term or long term, but you're trying to drive real growth for the business. But then when you've actually built a real business, a lot of times people are still in that same mode, which is everything is trying to add more growth on top of what we've already got. But when you're at scale, you can actually lose (laughs) what you've built. So trying to help, whether it's, you know, executives or just your manager understand that this thing we've got, whether it's, you know, a high conversion rate or, you know, good engagement on this feature, it could go away if we don't do these other things, and here's what it would look like if that goes away. That can be, you know, incredibly powerful. You know, I think we were fortunate at Pinterest in this regard in that we were a fast growing startup that stopped growing due to some changes in, in the market related to Facebook, and then actually once we had switched to growing primarily through SEO, there was an algorithm change that severely impacted our growth at, at one point in time. So that helped the company build more intuition of like, we're not guaranteed, you know, the gains from all the things we've built in the past. We need to do things to protect them, and protecting what we've got actually is increasingly important once you build scale because now you've built something really valuable already. And yes, we want to make it more valuable, of course, but it's hard to make it more valuable if you're eroding some of the gains you've already built. So that's, that's another element that I think can be pretty impactful.

   3. LRLenny Rachitsky29:44

      In your post on this topic, you have an awesome chart of product market fit over time illustrating the point you just made that it doesn't last and you have to kind of keep iterating to keep your product market fit. Like, you're by default falling behind if you're not continuing to push there, right?

   4. CWCasey Winters29:57

      Yeah. I th- I think the, the concept is, you know, user expectations just continue to go up every day, right? In terms of their expectations on user experience, on the value that they expect your product to provide, but also the competitive landscape, you know, in the market, right? It continues to get better. So yeah, if you're not continually pushing to make, you know, your product better or your user experience better, your, you know, latency better, then you're eventually, not n- necessarily tomorrow but maybe in a year or maybe in five years, you might find yourself fall out of product market fit entirely.... and that's a really dangerous place to be, 'cause then it's going to take a long time to figure that out and make adjustments, and then you probably have more technical debt to clean up to be able to get back to where you need to be, where the, the market has reached in terms of expectations. So, just doing work to make sure you never get in that situation is extremely valuable, in my opinion, and something that I think a lot of teams forget about.

   5. LRLenny Rachitsky30:57

      I think you're gonna create nightmares for a lot of founders listening to this right now.

   6. CWCasey Winters31:03

      (laughs) That's not the intention, but...

   7. LRLenny Rachitsky31:04

      It's a, no, it's a, it's a kick

10. 31:06 – 35:24

    The downfall of functional ops roles

    1. LRLenny Rachitsky31:06

       in the butt. Another post that I definitely wanted to chat about, maybe your spiciest post, maybe, I'm curious if there are others, is around operations team, op- product ops, and generally ops people. And-

    2. CWCasey Winters31:16

       Yep.

    3. LRLenny Rachitsky31:17

       ... this point that you made that ops is often a sign of inefficiency on a product team because in theory, a lot of the roles should be done by software eventually. I'd love to unpack this and hear your take on this.

    4. CWCasey Winters31:28

       I think the, the... I originally got the idea for the post in that I had written another essay on martech, um, and how martech, to be really successful, it's really got to target engineers more so than marketers, and that a lot of martech businesses just aren't very good businesses. Um, and I got- I think I got an invite to speak at a martech conference to a bunch of marketers about this post. And it's like, "Well, that sounds like a terrible idea, basically telling a bunch of marketers that, um, you know, what they're investing in isn't that important and that they're not the most important target customer." And I remember reading something about the conference that was like, "A conference for the growth of the marketing operations professional." And then I was like, "Oh, no. That's, that's not what I want in the industry at all." Like, having marketing ops means you suck at marketing. And obviously, that's a bit of hyperbole. I'm not against the, the concept of a marketing ops role or a product ops role. We, we have a product ops team, you know, at, at Eventbrite. But as someone who ran a double digit million marketing budget at Grubhub without marketing ops, because we invested in automation and we invested in process, it scares me when the first tactic people go to is to add people to help scale. There's nothing wrong with people, obviously. There's nothing wrong with operations people. The, the thing I have a problem with is normalizing ops as a distinct stable function, where operations roles are amazing, and, and how we utilize them at Eventbrite is their, their explicit job is to go find inefficiencies and build process or software to root out that inefficiency, so then they, they can go find other places to be more valuable. When you say, "Oh, their job is to do this manual process long-term," that's where I get super concerned, because you're not rooting out efficiency in how you build your company, and that's where I feel like a lot of this can go if you're not careful. Intercom has a really good blog post on this from a while back around their business operations team, and they basically up- upfront in that post say, "The, the goal of business operations did not exist," and that's... I, I definitely very much agree with that. So, I think in general, functional ops roles, whether it's product ops or marketing ops or, you know, whatever, they're a hack to deal with some sort of functional issue on your team. And it's totally okay to have functional issues. You know, startups are gonna have functional issues all over the place. But if the way they deal with that functional issue is by building larger and larger operations r- teams and roles, that's basically exacerbating, you know, an inefficiency issue, a functional issue. It's not fixing it. It's like, it's a form of empire building, and, and in general, empire building's something I don't have a lot of tolerance for. So, you're, you're making more of a function unable to operate without human intervention by saying the goal is to scale up marketing ops or product ops, whereas what the goal should be is, "Let's use our brains to run experiments to make us more functional with less people. We're more efficient. We could add more value to the customer and to the business." And if that means, you know, "I don't actually need to have this product operations job in a year," that's awesome. And guess what? If you've shown you've done a really great job at rooting out inefficiencies, every part of the company is gonna want you to do some other job, if that job is no longer valuable because you, you've done such a good job eliminating the need for it. So, there isn't this real concern that I'm gonna lose my job by being too effective at it. It's like, no, you're gonna show that you're just awesome at many types of jobs that, you know, product leaders or marketing leaders care about. So, that's my perspective.

    5. LRLenny Rachitsky35:12

       I love that. And this happened a lot at Airbnb. A lot of amazing ops people ended up moving into other roles once the role was not necessary, or they just wanted to do something else, and clearly people wanted them on their team 'cause they were killing it.

    6. CWCasey Winters35:23

       Indeed.

11. 35:24 – 40:47

    The CPO role: what it is and how to get there

    1. CWCasey Winters35:24

    2. LRLenny Rachitsky35:24

       One last question about the CPO role, and then I wanna shift a bit to just, like, product management and growth. What is the job of a CPO? For folks that are just like, "What the heck? What is this thing? What do you do all day?"

    3. CWCasey Winters35:35

       Yeah.

    4. LRLenny Rachitsky35:35

       And then what does it take to get there? Just, like, what should people work on most if they're trying to get to CPO someday?

    5. CWCasey Winters35:41

       So, you know, first off, when you think about, what's the job, you know, the way I think about it is, I'm responsible for leading and facilitating the development of products and features that deliver value for Eventbrite's customers that will translate into value for the business. And each of those words were chosen pretty carefully. Now, in terms of the scope of the function, a CPO role can lead a few different sub-functions. You know, in my case, I lead product management, product design, research, and growth marketing. But, you know, different roles have kind of some or not as many of those. Um, it, it can be pretty custom depending on the size of the company and what the, what the leader's skill sets are. To talk a little bit more depth about, like, the role, I, I think it's my job to make sure Eventbrite chooses the best possible product strategy based on the information we have, that we can adjust that strategy as we learn.... and continue to build, you know, that feedback loop. It's also my job to define and consistently improve the process through which we set our product strategy, how we prioritize projects, how we execute on them to make sure we're delivering, you know, that value to our customers, we're delivering those tangible business results. And to do that in a way where the rest of the company understands it and is able to participate in it as well, so this is things like identifying bottlenecks that prevent us from delivering, you know, value or quality or, you know, doing that at the detriment of speed, working with people across the company to remove those bottlenecks, making sure people outside of development are aware of what we're building, participating in the development and feedback of what we're building, as well as in helping deliver that, you know, for like a GTM perspective. And, and last but not least, and we've talked a little bit about this earlier, you know, training the team on what it means to be an effective product manager, product designer, user research, et cetera, at Eventbrite. And then, of course, hiring people who can augment our existing team, you know, on, on everything I just mentioned. So, you know, I'm accountable for what we build driving value for the business. And there's, of course, gonna be many times where what we build doesn't end up driving value. You know, it's hard to predict sometimes. But it's my job to kind of improve that conversion rate and the magnitude of impact over time. You know, it might, might not be that everything we build delivers value but I want most of it to, and I want the impact of, of that value to be higher and higher over time. So, you also asked about what it takes to get to the CPO role, um, and I think my journey's been more irregular (laughs) than, than most of the people you probably talked to. You know, product management, when I started my career, you know, it was, it was all waterfall. It was built around massive releases. It was a totally different job from what we do now. Um, marketing was a lot more, you know, agile, in the lowercase sense of agile. And it mapped to my mind better as someone who was, like, really influenced, you know, by the book The Goal. So, I think the tangible pieces of advice to get to this level that may be helpful is... I always focused on where I thought there was leverage. I wanted to learn everything that I could and focus on the things that had a big impact regardless of the org structure or the career path that meant. I wanted to really have a deep understanding of the entire business so I knew just what was worth focusing on to help the business. I think one of the things that's different about being a chief product officer versus, you know, other product roles is how much of a company leadership role it is versus a functional leadership role. You're expected in this role to optimize for the entire company even at the expense of what's good for your team. So, you really have to learn how to optimize for company first. That's, like, a key thing to learn that I think new executives can struggle with. And one advantage I think I had is I'd basically been working with executives since my first job at Apartments.com, so I learned to speak their language and understood what they cared about pretty early in my career. And, you know, th- this is a really important element: assume that questions from them are them trying to learn versus them assuming you don't know something and testing you about it. I find that a lot of people get intimidated by executive questions when the executive's just trying to understand things, and then that changes the interaction you can have. The, the other element that served me well was just refusing to specialize. I thought if I could learn all the skills that would allow me to combine them to work on the most important things versus only work on the thing I knew how to work on, and that definitely led to slower visible progress in terms of career growth or titles, but it was a much faster path to the true executive role because I could speak better with CEOs about more topics than most of my peers. Obviously, this is all my individual experience. There are many paths to get to, to this type of level, but those are some things that

12. 40:47 – 45:14

    The spectrum of product people

    1. CWCasey Winters40:47

       have worked for me.

    2. LRLenny Rachitsky40:48

       That was such an incredible definition, and so much good advice there. And this is a good segue to another area that you have really interesting insight on around the spectrum of product people. I- when I think of you, I think of two-by-twos, and this is, I think, just a spectrum, which is unusual for a-

    3. CWCasey Winters41:03

       Yeah.

    4. LRLenny Rachitsky41:03

       ... CASEY framework. I'd love to hear your take on how you think about the spectrum and around upscaling PMs to move along that spectrum.

    5. CWCasey Winters41:09

       The idea is, and this is something, you know, I was inspired from talking with Omar, who, who runs product at Cambly. He used to run core product at Pinterest. It's this idea of, you know, uh, any product team is like a gang of misfits, right? They all come from different backgrounds. You know, most people didn't start as a, you know, a product manager their first job, right? They might have been in sales or in marketing or analytics or engineering, right? So everyone's bringing kind of these different skill sets to the table, but the, the main spectrum that, you know, I've observed in, in product teams of, of any decent size is that you have two extreme types of, you know, product managers per se. Um, you know, on, on perhaps the left side of the spectrum, you have the crazy innovator types. They have so many different ideas. They pay attention to, you know, every single change in the industry. They all know all about the latest, you know, Apple API or Snapchat's latest product feature, right? Those people are gonna have ideas all the time. Actually, probably most of those ideas are gonna be bad, but, like, one out of 10 is gonna be just a game changer. And they're generally not super great at turning that idea into action. And then, you know, on the right s- on the extreme right side of the spectrum will be your typical executional-focused PM. And they can do a really good job of taking a strong strategy and turning it into action that creates value for the customer.... but they generally don't know what's going on in the industry. They can't think of a totally new product idea themselves. They're gonna need support from above to be able to push them in the right direction, and then they got it from there. So the ... When you think about recruiting, what we all want as, like, CPOs in terms of people we bring into our team is we want people in the middle. We want people who are strategic, they understand what's going on in the industry, they can generate some good ideas, but they could also turn it into something real that delivers value, you know, for the customer and the company. And there just aren't a ton of those people, (laughs) um, you know, in the world. Not as many as, as we would like to recruit. So, you know, as a product leader, if I'm erring on the side of, like, which side of the spectrum I want people from, I generally will take people who are good at execution over people who are good at generating ideas because, of course, there's al- always too many good ideas that a company need to focus and, and, and execute well on the best ones. Whereas if I were a VC, I would probably bias to the people on the left because I don't need every company to work. If I invest in 10 different entrepreneurs who have crazy ideas and one of them works and becomes the next Airbnb, turns out I've done inc- incredibly well, you know, as, as a venture capitalist. So the challenge you practically deal with as a product leader is you end up re- recruiting and managing and growing a lot of executional people who can get stuff done, but if they wanna get to the director level, or if they wanna get to my level, they need to get more strategic, and we don't have good ways to kind of turn great executors into great strategists, you know, as, as in general, like, a, a product, you know, uh, function. So I- I started investing in a lot of different things here. Obviously, I built some programs from Reforge around product strategy. A lot of my team goes to those to try to learn. I've also been doing a lot of, you know, mentorship with the team to try to teach them what it looks like to do that well. I've had, you know, people come in to speak with the team, like you and, and many other great product folks, to show, you know, my team what great looks like and how people like you developed your skills. And I'm trying lots of different things to try to move, you know, more of the team to the middle where they can be that, you know, optimal strategist that still retains that ability to deliver great value on top of the strategy versus just have ideas that can't be executed on, and it's definitely a work in progress. It's, it's a lot of, a lot of different tactics to try to build that skill set int- inside the team and scale it and, you know, definitely something I feel like I'm still working

13. 45:14 – 47:04

    How to level up your skills

    1. CWCasey Winters45:14

       on.

    2. LRLenny Rachitsky45:14

       What I'm hearing is a lot of the, k- kind of the biggest upside for PMs to develop is basically to become more strategic, and all the things you've shared are just ways, or a lot of ways, to just become better at strategies. It's interesting that that's, like, what you found to be the most essential piece for PMs to often level up at.

    3. CWCasey Winters45:33

       Like you said, it depends on the level, right? So early on in your career as a PM, you're gonna get the most value by showing that you can ship real things to customers and that the customers like them.

    4. LRLenny Rachitsky45:43

       (laughs)

    5. CWCasey Winters45:43

       Right? That's by far the most important thing. But if you wanna start managing groups of PMs, if you wanna start running a business unit or a pillar or a theme, I'm going... I, as a chief product officer, I'm gonna expect you to be able to write that strategy doc without me. And, you know, what I found in, you know, whether it's through the advising roles or through coming into Eventbrite is just a lot of people couldn't do that step. And that means when you try to become a product leader at the company and, you know, the CEO expects that from you and you can't do it, you're gonna, you know, like set yourself up to, like, really cap hard on, on how fast your career can grow, and you'll get stuck, you know, whether it's at the senior product manager level or at the group PM level 'cause you can't show that you can drive decision-making on your own and that you can push forward new ideas that are gonna help the company. So that's definitely where I've seen the biggest bottleneck in terms of skill sets. Obviously, there's lots of important skill sets you wanna build as a, as a PM, but that one to get to the top is the great filter.

    6. LRLenny Rachitsky46:43

       That's awesome advice for folks listening that are trying to figure out, "What should I work on?" It's kind of simple a lot of times. Just get better at strategy, and it feels like it elevates you in so many other ways.

    7. CWCasey Winters46:52

       Yeah. And of course, we could talk for-

    8. LRLenny Rachitsky46:54

       (laughs)

    9. CWCasey Winters46:54

       ... you know, hours about what it means to get better at strategy and some of the tactics there. Um-

    10. LRLenny Rachitsky46:58

        That could be a follow-up.

    11. CWCasey Winters46:59

        ... 'cause I know some PMs-

    12. LRLenny Rachitsky46:59

        Follow-up pod.

    13. CWCasey Winters47:00

        ... struggle with that. Yeah.

    14. LRLenny Rachitsky47:02

        Okay.

    15. CWCasey Winters47:02

        Podcast number two.

    16. LRLenny Rachitsky47:02

        Podcast number two. Let's

14. 47:04 – 50:35

    New growth trends, tactics, and strategies

    1. LRLenny Rachitsky47:04

       book it. Okay. So I can't let you go without talking about growth. Everyone's always trying to figure out how do we grow our company, what can we do to-

    2. CWCasey Winters47:11

       Right.

    3. LRLenny Rachitsky47:11

       ... accelerate growth. I know you're modest, but I think you're one of the smartest people in the world on this stuff. And so I just wanna touch on a couple things in the time that we have here. One is with thing... with paid growth becoming increasingly more expensive and difficult, especially with Apple's recent changes, SEO forever becoming more crowded, sales being always expensive, it's just, like, tough out there for a lot of startups to grow. Are you seeing any interesting or new growth channels or tactics that folks can explore or consider that maybe work for companies that you're, that you're looking at?

    4. CWCasey Winters47:47

       It's not that there are new channels per se unless you include, you know, tokens from, like, Web3, which, which I do not. It's more that there are ways to get leverage on your channels through better flows or lifetime value that companies are figuring out. So for example, you know, at Eventbrite, we unified what were separate direct response and lead generation flows in our performance marketing to acquire creators, and now it just takes less effort. We're getting better CPAs, and sales now has the opportunity to pick up, you know, any product qualified lead, you know, from a direct response customer who may... who may need a little bit more help, and they have the data to now determine if there's high enough value to justify it. So, you know, this concept is being dubbed product-led sales, and it's this idea that you can unify self-service loops...... in a B2B business, which are typically driven by product, and your sales loops into one more complex giant loop that operates more efficiently and breaks down the silos. And I think you're gonna see an explosion in B2B companies that learn how to unlock that and get sales and product and marketing to be working as one larger cross-functional team in building an engine that optimizes all of their skill sets. So that's something I'm pretty excited about. But we're definitely in the early days there.

    5. LRLenny Rachitsky49:05

       That's, that's awesome. I was gonna ask you if there's any trends you're seeing around growth, and clearly that's one. Are there, are there any other trends, just things happening in the growth world?

    6. CWCasey Winters49:16

       Yeah, sure. I, I think there was, you know, this conventional wisdom to just focus on building until you found product market fit, and then you can worry about growth. And of course, there's, there's some truth in that statement. But now as I'm talking with more and more founders, and I'm, I'm sure you're, you're seeing this yourself, is we're seeing founders who are thinking about building growth loops into their product before they find product market fit. And it's not so that they can prematurely scale before they have product market fit. It's so that when they find product market fit, they have that built-in distribution advantage to grow once they're ready. And founders are starting to intuit, you know, what I've written about a bit, as, as well as you, which is that scalable acquisition, or what we call an acquisition loop, is a requirement for product market fit. Like, if you got a product that retains well and you can't find more use for it, I don't think that's product market fit. So it's really exciting to see that evolution and to see founders think about, like, it's not about getting a bunch of users before you have a product that works. It's about thinking strategically about how this product's gonna grow itself when it's ready to do so. So I'm really excited to see the next generation of founders, you know, build that muscle early on, and, and, and also, you know, leverage it when they're ready instead of just like, "Oh, I'm gonna throw a bunch of paid ads at it and it's gonna work." Um, so, so that's something I'm really excited about.

15. 50:35 – 51:54

    Casey’s two stages of growth: kindle strategies and fire strategies

    1. CWCasey Winters50:35

    2. LRLenny Rachitsky50:35

       On that topic, when should companies focus on growth? And as a second question, when do you think they should hire a head of growth or someone full time focused on growth?

    3. CWCasey Winters50:43

       Like I mentioned, uh, while you don't wanna focus on growth before product market fit, you wanna be thinking about how your product can grow scalably, you know, pretty early on. So, you know, early growth definitely needs to be done by the founders. I tend to separate growth into two phases. I call the first k- phase kindle strategies. These are those non-scalable hacks to get your early users, and I think those are generally done by founders, maybe some early team members. Fire strategies are the ones that drive scale. That's, you know, what you were mentioning, content loops, sales loops, viral loops, paid acquisition. And to me, the goal of your kindle strategies, these like non-scalable hacks, they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users. And it's once you unlock a fire strategy, that's when I think you think about hiring someone full time on growth to fully harness that new growth loop you've built. That could be a salesperson if it's sales. It could be, you know, a growth PM if it's viral or UGC content, or it could be a performance marketer if it's ads. But it's once it's like, "Okay, we've sequenced to a growth strategy that actually scales, let's go find someone who's awesome at that who can make it, you know, 10X better." That's how I think about it.

16. 51:54 – 54:05

    Under appreciated growth strategies

    1. CWCasey Winters51:54

    2. LRLenny Rachitsky51:54

       Maybe a last question. Is there... Is there kind of an underappreciated or underinvested in growth strategy, growth tactic, things that you're just like, "Oh, wow, this seems to be working better than people may think"?

    3. CWCasey Winters52:06

       Um, yeah. Well, I, uh, I still think data network effects are underrated. I think a lot of people confuse the idea of data network effects with data as a product you can charge people for, especially, like, businesses. And I get it. Like, a lot of businesses, like, you can't charge them for data because they don't know how to use data super well, especially SMBs. But what data network effects are is leveraging product usage data to make the product value stronger and stronger over time. You know, that could be personalized results, you know, in the case of Pinterest, or in the case of Eventbrite, better targeting data for advertising to find people who are more likely to be interested in your event. And I think especially with Facebook and Apple's platform changes, your product being able to generate its own data versus just relying on the big platforms to do all the work for you, that's a real edge that companies are starting to wake up to, and it's obviously something that's worked well for me in the past, you know, at Pinterest and certainly now at Eventbrite.

    4. LRLenny Rachitsky53:05

       So there's a couple questions that I had at the top that I skipped that I thought I'd come back to. I know that you're a big video game guy, and I love that at the bottom of your post you always share the music that you're listening to. So I was just gonna ask, what's the game you're playing these days? Anything you recommend? And then what are you listening to?

    5. CWCasey Winters53:21

       Yeah. I'm currently playing Cyberpunk 2077 on the PS5, which is fun. But I recently finished Horizon Forbidden West, and that was excellent, really great science fiction game. Um, you know, on the music side, one of my favorite bands is this band called Broadcast, and they never really played live a whole lot, and, um, their, their singer died, uh, a few years ago. But they recently came out with, uh, a recording of a bunch of their live sessions that they recorded on the BBC, and it's, it's like, it's like getting this time capsule from the past of some of their, you know, early live sessions. That's been really great. So I've been, I've enjoying that record quite a lot lately.

17. 54:05 – 55:08

    Where to find Casey

    1. CWCasey Winters54:05

    2. LRLenny Rachitsky54:05

       Awesome. K.C.'s picks, get 'em here. Get 'em here now. K.C., I feel like I was successful in extracting many nuggets in our hour together. Really appreciate your time. Where can folks find you online, and how can people that are listening be helpful to you?

    3. CWCasey Winters54:20

       Blog at kcaccidental.com. I'm semi-active on Twitter, uh, at @1Kceman. And, you know, always I focus on paying it forward. Like, help the next generation of companies, of PMs, of, of marketers get better at their craft and, and build better businesses. You know, and if, uh, if you he- (laughs) if you're searching for a cool event, check out the Eventbrite app, of course. We always would appreciate that.

    4. LRLenny Rachitsky54:46

       Love it. Uh, amazing, K.C., what a great way to end it. Uh, thank you again for being here.

    5. CWCasey Winters54:51

       Thanks so much.

    6. NANarrator54:53

       (instrumental music)

    7. LRLenny Rachitsky54:53

       That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast, and even better, leave a review, which helps a lot. You can also learn more at lennyspodcast.com. I'll see you in the next episode.

Episode duration: 55:08