Why most product managers are unprepared for the demands of a real startup | Casey Winters

Casey Winters: 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.

The Interview Begins

Lenny: Pinterest, Airbnb, Reddit, Canva, Hipcamp, Thumbtack, Fair, Tinder, Eventbrite. What do these companies have in common? Casey Winters, Casey has worked with and advised more consumer companies on their product and growth strategy than anyone in the world. He’s also very generous with his time and often sets time aside to help founders and product leaders. I always learned so much talking to Casey, and I’m excited for you to hear this episode. In our chat we covered Casey’s advice on making trade offs as a product leader, justifying non-sexy product investments, the spectrum of product people and how to level up your skills, new growth trends and tactics that he’s seeing, when to focus on growth, and a bunch of advice on growth strategy, and so many other things. As a bonus, we’re going to be doing a live AMA with Casey in my newsletter Slack community on August 5th at 10:00 AM Pacific time, so if you’d like to ask Casey any questions, make sure to get there. Until then enjoy this episode with Casey Winters. Hey Casey Winters, what do you love about Coda?

Casey’s Career Journey

Casey Winters: Coda’s 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, 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 LKRs, run annual planning, build your roadmap, 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.

Challenges of a CPO

Lenny: 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’s 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.

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

Managing Up and Trade-Offs

Casey Winters: Very kind, happy to be here.

Balancing Simplicity and Features

Lenny: 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 you have to click on, see additional experiences. 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 and growth?

Casey Winters: 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 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 going to do 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, because 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.

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 we’ll have results. And we now call these roles growth, but 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 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 the business to reignite 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 with Airbnb on the demand side, with Pocket. And then I went to a VC named Greylock Partners and worked with their companies on growth and scaling. And then I just independently started working as a full-time advisor with companies like Eventbrite, Tinder, Thumbtack, Canva. And after doing that for a couple years, Eventbrite opened this chief product officer role and they asked me to take it, so now I’ve been doing that for three years now.

Perceived Simplicity in Practice

Lenny: That’s an excellent segue to our next little segment that I want to get into, which is 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. You’re currently a chief product officer at Eventbrite, which is a company that I love, I have so many friends there and they’re all amazing, such a big fan of the company. And I know a lot of listeners are maybe thinking about becoming CPO someday as a goal.

Casey Winters: Yep.

Funding Unsexy Product Improvements

Lenny: 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.

Showing the Cost of Inaction

Casey Winters: Sure.

Operations Teams and Efficiency

Lenny: Cool.

Casey Winters: Yeah.

The Role of a CPO

Lenny: 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 then across the company, so I’m curious just to hear what you’ve learned around how to communicate trade offs and internal communication?

Casey Winters: Yeah, one of the things I found, especially during the pandemic at Eventbrite, where we weren’t obviously hiring a lot of people and we had 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 or escalate them with me in particular. And some of these were really tough situations, so then later on, I’d ask why something went wrong or why we didn’t achieve a goal. And I get 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. Yeah, of course I don’t understand this situation because you haven’t told me about it. How am I supposed to evaluate things fairly if you don’t let me know what’s really going on, so these people on my team thought that being a leader was handling it the best they could given the circumstances when in many cases the right way is to escalate the issue so that perhaps I could 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 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. I find that in general people just way under communicate upward inside of companies. And then they’ll complain that executives are out of touch when they aren’t telling executives what the executives need to know. Then when people inside a company do try to communicate upward a lot of times they’re so in the weeds that 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 I don’t know if you’ve ever seen Ocean’s Twelve, but as a joke, they invite Matt Damon to this business meeting and they just talk in code as a prank on him.

And 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. It’s like you’re speaking another language. One of the ways I try to frame it to my team is 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, which is 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 what you’re building? And I find that many times when non-executives are presenting to execs, they’ll start on like chapter six, so 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. And I’ve definitely seen people with the opposite problem as well, which I call starting at the beginning of the time where you come into a meeting with the CEO or with the CFO or something.

And you basically spend the first 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 used up your allotted time, so I try to coach my team to be in the middle. Like don’t start on chapter six of the story, but also don’t start with a textbook on the English language either. You want to 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 it’s a lot of work to really dial that in across different types of people you’re trying to communicate that story to because 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 going to need to hear some very different things then say the CPO of the company, or the CEO of the company, so it’s a challenge I see quite frequently.

The Product Manager Spectrum

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

From Executor to Strategist

Casey Winters: 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 make it a big success or fail moment, so there’s a few things that I do. One is if there is a big 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 going to 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 going to ask about is why, so you want to weave that into the early story and not wait for her to ask.

You kind of role play the entire thing based on the different people that they’re going to be communicating with. Something 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 impersonate them and help you understand what they’re going to 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 going to be less surprised in the meeting about what you’re talking about, that you’ve gotten any major concerns brought to your attention before the big meeting.

And that helps de-risk how poorly a meeting like that can go, so definitely at the individual presentation level, doing that pre-meeting. What I’m working on a lot now is trying to have more of a scaled approach to training this type of upward communication. And what types of frameworks, what types of structure tend to work for Eventbrite and making sure that everyone on my team is just really well versed in that and comfortable in it because of course, confidence projection is a key part of these types of meetings as well.

New Growth Channels and Strategies

Lenny: 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 an ICPM should spend on preparing for these things just to set a little bit of a reference point?

Casey Winters: Well, it’s an interesting question because I think different people have different styles on how they want to handle this. I’d say the way my brain works in these situations 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 want to hit. I’m going to show up as more comfortable, I’m going to show up as more dynamic, and I’m going to 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 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 want to nail. And I found it requires a different amount of investment for different people on my team, so 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. I’ll give an example from my Pinterest days, the primary way with which you interfaced on any key strategic topic was product review, right? You’d go in and you talk to Ben, our CEO and Jack our head of product. And 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 cast doubt on the entire rest of that meeting.

Because, 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 going to ask this question, then this question, then this question. Based on the material I’m seeing from you, how well are you prepared to answer those questions? Different execs might be 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. 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 asked what possible questions can 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? But because if I don’t the chances of the meeting you’re having a negative outcome just increased dramatically.

New Trends in Growth

Lenny: 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 the ones you’re talking about.

Casey Winters: Absolutely. I mean, for better or worse, the way that a lot of key decisions are made inside companies are through these types 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 and I have definitely made mistakes in our career in important meetings in the past, but I think 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 going to make it have a more negative result.

And now I’m pretty accurate. And look sometimes you just didn’t have enough time and it is what it is. But now I know, okay, I know I’m not quite prepared for this and 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, 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 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 going to 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.

When to Focus on Growth

Lenny: Speaking of spending more time, another topic that you shared with me that you’re thinking a lot about as a CPO is keeping the Eventbrite product simple 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 survive, and keep adding more power.

Casey Winters: Yeah, Scott Belsky who’s the chief product officer of Adobe. He has this concept of the product life cycle you’re probably familiar with, but I’ll explain it to your listeners, which is 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 I’ve done a lot of research 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. One is okay if you build out more complex functionality, un-bundle it over time, like Facebook Messenger, Uber Eats have done, right? At Pinterest, we did a heavy investment in progressive disclosure, which is 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 open up more of the full suite of the product.

Then there’s just proactive training. You can get on a video call with your customers or 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. 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 interfaces that cleanly separate the two, maybe that more complex experience also bundles in training. What I found is that just none of these really worked that well for the Eventbrite 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 people putting on a hundred events per year that 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 they build up their business, so segmentation doesn’t really work that well. 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 going to confuse them. 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 going to 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 there are areas where we do this well and areas where we’re still 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 WhatsApp, where 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 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, it would take less than a second to figure out how to use the more advanced stuff, but it’s effectively kind of hidden if you’re not looking for it. That’s what we aspire to at Eventbrite. And in some cases we’re doing well. And in some cases, we definitely have some work to do.

Underrated Growth Strategies

Lenny: Is there an example of a win in that direction in the Eventbrite product that you’re proud of using this model or even something that’s like, oh man, this is really broken?

Casey Winters: Yeah, 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 our creators do a lot of their own marketing to try to get people to come to their events and transact on Eventbrite in the process. But our event creators, they’re not professional marketers, they try to figure these tools out, so we built a product that allows them to automate their Facebook advertising to get better results, supercharged by our data. And the product’s working really well, but we found is that there are certain segments that, I want to geek out on this a little bit, right.

They want to figure out all the different target segments and optimize their creative, and then there are many creators who just want it done for them. We’ve been able to build some interfaces where the default is 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 do more of this yourself, so that’s an area where I wouldn’t say we’ve perfected it, but we’ve now really understood those different types of users and a have easy pass for both of them to be successful, so I’m really happy with that.

Closing Personal Recommendations

Lenny: Awesome. Another topic that you wrote about that kind of touches on the stuff we were just talking about is justify 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… The default is let’s do that later, we got to hit our fricking metrics, we’ve got to drive growth. And you had some really interesting insights on how you think about justifying these sorts of things. And so I’d love to hear that from you?

Casey Winters: The idea is that some of the most impactful projects that product teams can work on at scale, not early stage startups per se, but at scale are the hardest to measure. And because of that, they just get chronically underfunded. It’s that old adage, what gets measured gets managed, right? For things like user experience, or performance, or developer velocity, or just a product area that’s deemed un-sexy, like growth used to be back in the day, I walk 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 one of the main takeaways besides some of those tactics 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? If you’re a PM, you want to be approaching this from a well, my engineering manager and my design leader also bought in that we need to work on performance or we’ve all aligned that the user experience is not going in quite the direction we want, and we want to head some problems off that may not improve metrics today, but could certainly decline metrics tomorrow. And if you can get a small team, what two, three people aligned on the importance of something that’s deemed un-sexy. It’s a lot easier to start to build this game plan around metrics or running small tests or structuring OKRs to not only prioritize this work, but to show some really massive impact. Which could then get the rest of the company much more excited to make investments themselves.

Lenny: What I’m hearing is step one is just get your kind of peer leaders aligned behind something that may not obviously be something your leaders want you to do, is that right?

Casey Winters: Absolutely, yep.

Lenny:

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 some that maybe isn’t going to move metrics or is that the core of it?

Casey Winters: Well, yeah. I mean, definitely it’s hard when you can’t create a metric that they can understand. I think the other area to think about is 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 what you’ve built, so trying to help whether it’s executives or just your manager, understand that this thing we’ve got, whether it’s a high conversion rate or 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 incredibly powerful. 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 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 one point in time, so that helped the company build more intuition of like we’re not guaranteed 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 another element that I think can be pretty impactful.

Lenny: 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 keep iterating to keep your product market fit like you’re by default falling behind if you’re not continuing to push there, right?

Casey Winters: Yeah. I think the concept is user expectations just continue to go up every day in terms of their expectations on user experience, on the value that they expect your product to provide, but also the competitive landscape in the market continues to get better. Yeah, if you’re not continually pushing to make your product better, your user experience better, your latency better, then you’re eventually not necessarily tomorrow, but maybe in a year, maybe in five years, you might find yourself fall out of product market fit entirely. And that’s a really dangerous place to be, because 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 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. It’s something that I think a lot of teams forget about.

Lenny: I think you’re going to create nightmares for a lot of founders listening to this right now.

Casey Winters: That’s not the intention, but-

Lenny: No, it’s a kick in the butt. Another post that I definitely wanted to chat about. Maybe your SPST post, maybe I’m curious if there are others is around operations team, product ops and generally ops people.

Casey Winters: Yep.

Lenny: And 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?

Casey Winters: I think I originally got the idea for the post in that I had written another essay on MarTech. And how MarTech to be really successful, it’s really got a target engineers more so than marketers. And that a lot of MarTech businesses just aren’t very good businesses. And 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. I’m basically telling a bunch of marketers that 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 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 concept of a marketing ops role or a product ops role, we have a product ops team 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 thing I have a problem with is normalizing ops as a distinct stable function where operations rules are amazing and how we utilize them at Eventbrite is their explicit job is to go find inefficiencies and build process or software to root out that inefficiency, so then 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 front in that post say the goal of business operations is to not exist, and I definitely very much agree with that. I think in general functional ops roles, whether it’s product ops or marketing ops or 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. Startups are going to have functional issues all over the place, but if the way they deal with that functional issue is by building larger and larger operations teams and roles. That’s basically exacerbating an inefficiency issue, a functional issue, it’s not fixing it. It’s a form of empire building and in general empire building is something I don’t have a lot of tolerance for.

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 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’s going to want you to do some other job if that job is no longer valuable, because you’ve done such good job eliminating the need for it. There isn’t this real concern that I’m going to lose my job by being too effective at it. It’s like, no, you’re going to show that you’re just awesome at many types of jobs that product leaders or marketing leaders care about, so that’s my perspective.

Lenny: I love that. And this happened a lot at Airbnb, a lot of amazing office 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 because they were killing it.

Casey Winters: Indeed.

Lenny: One last question about the CPO role, and then I want to shift a bit to just 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?

Casey Winters: Yeah.

Lenny: 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?

Casey Winters: First off, when you think about what’s the job, 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. In my case, I lead product management, product design, research, and growth marketing, but different roles have kind of some or not as many of those, it can be pretty custom depending on the size of the company and what the leader’s skill sets are. To talk a little bit more depth about the role. 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 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 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 value, or quality, or 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 for like a GTM perspective. And last but not least, and we’ve talked a little bit about this earlier, 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 on everything I just mentioned, so I’m accountable for what we build driving value for the business. And there’s of course going to be many times where what we build doesn’t end up driving value. It’s hard to predict sometimes, but it’s my job to improve that conversion rate and the magnitude of impact over time. It might not be that everything we build delivers value, but I want most of it to, and I want the impact of that value to be higher and higher over time. You also asked about what it takes to get to the CPO role. And I think my journey’s been more irregular than most of the people you probably talk to. Product management when I started my career, it was all a waterfall. It was built around massive releases, it was a totally different job from what we do now. Marketing was a lot more agile in the lowercase sense of agile and it mapped to my mind better as someone who’s really influenced by the book, The Goal.

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 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 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 what advantage I think I had is I’ve 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 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 is just trying to understand things. And then that changes the interaction you can have. 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 this type of level, but those are some things that have worked for me.

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

Casey Winters: Yeah.

Lenny: I’d love to hear your take on how you think about the spectrum and around up-scaling PMs to move along that spectrum?

Casey Winters: The idea is, and this is something I was inspired from talking with Omar who runs product at Cambly. He used to run core product at Pinterest. It’s this idea of any product team is like a gang of misfits, they all come from different backgrounds. Most people didn’t start as a product manager, their first job, they might have been in sales, or in marketing, or analytics, or engineering, right. Everyone’s bringing these different skill sets to the table. But the main spectrum that I’ve observed in product teams of any decent size is that you have two extreme types of product managers per se, and on perhaps the left side of the spectrum you have the crazy innovator types, they have so many different ideas, they pay attention to every single change in the industry, they all know all about the latest Apple API or Snapchat’s latest product feature.

Those people are going to have ideas all the time. Actually, probably most of those ideas are going to be bad, but one out of ten’s going to be just a game changer and they’re generally not super great at turning that idea into action. And then 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 going to need support from above to be able to push them in the right direction and then they got it from there. When you think about recruiting, what we all want as 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 can also turn it into something real that delivers value for the customer and the company.

And there just aren’t a ton of those people in the world. Not as many as we would like to recruit, so as a product leader, if I’m airing on the side of 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 always too many good ideas that a company need to focus 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 incredibly well as a venture capitalist. The challenge you practically deal with as a product leader is you end up recruiting, and managing, and growing a lot of executional people who can get stuff done, but if they want to get to the director level or if they want to get to my level, they need to get more strategic.

And we don’t have good ways to turn great executors into great strategists as in general, like a product function, so I’ve started investing in a lot of different things here. Obviously I’ve built some programs for Reforge around product strategy. A lot of my team goes to those to try to learn. I’ve also been doing a lot of mentorship with the team to try to teach them what it looks like to do that well. I’ve had people come in to speak with the team like you and many other great product folks to show 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 more of the team to the middle, where they can be that 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 a lot of different tactics to try to build that skill set inside the team and scale it. And definitely something I feel like I’m still working on.

Lenny: What I’m hearing is a lot of 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.

Casey Winters: Like you said, it depends on the level, right. Early on in your career as a PM, you’re going to get the most value by showing that you can ship real things to customers and that the customers like them, like that’s by far the most important thing. But if you want to start managing groups of PMs, if you want to start a running a business unit, or a pillar, or a theme. I as a chief product officer, I’m going to expect you to be able to write that strategy doc without me. And you know what I found, 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 the CEO expects that from you and you can’t do it, you’re going to set yourself up to really cap hard on how fast your career can grow. And you’ll get stuck, whether it’s at the senior product manager level or at the group PM level, because you can’t show that you can drive decision making on your own and that you can push forward new ideas that are going to 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 want to build as a PM, but that one to get to the top is the great filter.

Lenny: 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.

Casey Winters: Yeah, and of course we could talk for hours about what it means to get better at strategy and some of the tactics there.

Lenny: It could be a follow up.

Casey Winters: Because I know some PMs who struggle with that.

Lenny: Follow up.

Casey Winters: Yeah.

Lenny: Okay.

Casey Winters: Podcast number two.

Lenny: Podcast number two, let’s 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?

Casey Winters: Right.

Lenny: What can we do to 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 want to touch on a couple things in the time that we have here. One is with paid growth becoming increasingly more expensive and difficult, especially with Apple’s recent changes.

Casey Winters: Yep.

Lenny: SEO forever becoming more crowded, sales being always expensive. It’s just 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 looking at?

Casey Winters: It’s not that there are new channels per se, unless you include tokens from like Web3, 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. For example, at Eventbrite, we unified what we’re 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 any product qualified lead from a direct response customer 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.

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 going to 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 and 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.

Lenny: That’s awesome. I was going to ask you if there’s any trends you’re seeing around growth and clearly that’s one. Are there any other trends, just things happening in the growth world?

Casey Winters: Yeah, sure. I think there was 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 some truth in that statement, but now as I’m talking with more and more founders and I’m sure 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 what I’ve written about a bit 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 users 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 going to grow itself when it’s ready to do so. I’m really excited to see the next generation of founders build that muscle early on and also leverage it when they’re ready instead of just like, oh, I’m going to throw a bunch of paid ads at it and it’s going to work, so that’s something I’m really excited about.

Lenny: 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?

Casey Winters: Like I mentioned, well, you don’t want to focus on growth before product worked fit. You want to be thinking about how your product can grow scalable pretty early on, so early growth definitely needs to be done by the founders. I tend to separate growth into two phases. I call the first 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 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 growth PM, if it’s viral or you just see 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 10X better. That’s how I think about it.

Lenny: Maybe a last question, is there is kind of an underappreciated or under invested in growth strategy, growth tactic, things that you’re just like, oh wow, this seems to be working better than people may think.

Casey Winters: Yeah. Well, 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 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. That could be personalized results 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 at Pinterest and certainly now at Eventbrite.

Lenny: 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 going to ask what’s the game you’re playing these days. Anything you recommend and then what are you listening to?

Casey Winters: 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. On the music side, one of my favorite bands is this band called Broadcast and they never really played live a whole lot and their singer died a few years ago, but they recently came out with a recording of a bunch of their live sessions that they recorded on the BBC. And it’s like getting this time capsule from the past of some of their early live sessions. That’s been really great, so I’ve been enjoining that record quite a lot lately.

Lenny: Awesome. Casey’s picks get them here, get them here now. Casey, I feel like I was successful in extracting many nuggets in our hour together, I really appreciate your time. Where can folks find you online and how can people that are listening be helpful to you?

Casey Winters: Blog@caseyaccidental.com, I’m semi-active on Twitter @onecaseman, and always I focus on paying it forward, like help the next generation of companies, of PMs, of marketers, get better at their craft and build better businesses. And if you’re searching for a cool event, check out the Eventbrite App of course, we always would appreciate that.

Lenny: Love it. Amazing Casey, what a great way to end it. Thank you again for being here.

Casey Winters: Thanks so much.

Lenny: 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.

Glossary

English	中文
acquisition loop	获客循环
Adobe	Adobe
AdWords	AdWords
Airbnb	Airbnb
apartments.com	apartments.com
B2B	B2B
Ben	Ben（Pinterest CEO）
Cambly	Cambly
Canva	Canva
Casey Winters	Casey Winters
content loops	内容循环
CPA (Cost Per Acquisition)	CPA
CPO (Chief Product Officer)	首席产品官
data network effects	数据网络效应
direct response	直接响应
Eventbrite	Eventbrite
Facebook Messenger	Facebook Messenger
Fair	Fair
fire strategies	燎原策略
Greylock	Greylock
Greylock Partners	Greylock Partners
group PM	组级产品经理
growth PM	增长产品经理
GrubHub	GrubHub
hack	hack
Hipcamp	Hipcamp
Intercom	Intercom
IPO	IPO
Jack	Jack（Pinterest 产品负责人）
kindle strategies	点火策略
lead generation	线索生成
Lenny	Lenny
MarTech	营销技术
MAU (Monthly Active Users)	月活跃用户
Omar	Omar
paid acquisition	付费获客
performance marketer	效果营销人员
Pinterest	Pinterest
Pocket	Pocket
product led sales	产品驱动销售
Product Manager	产品经理
product market fit	产品市场契合度
product ops	产品运营
product qualified lead	产品合格线索
product review	产品评审
progressive disclosure	渐进式披露
Reforge	Reforge
sales loops	销售循环
scalable acquisition	可规模化获客
Scott Belsky	Scott Belsky
self-service	自助服务
SEO	SEO
Series A	A 轮
SMBs (Small and Medium Businesses)	中小企业
SPST	SPST
technical debt	技术债
Thumbtack	Thumbtack
Tinder	Tinder
Uber Eats	Uber Eats
VC (Venture Capital)	风险投资
viral loops	病毒循环

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