# Welcome 20Growth: How To Hire a Head of Growth? What are Signs of World-Class Talent? How To Structure the Process? How To Onboard Growth Teams? The Relationship Between Head of Growth and CEO and more with Casey Winters

Chief Product Officer @ Eventbrit

Sep 22, 2021 · 43 min · 9,751 words
Speakers: Harry Stebbings, Casey Winters
Source: https://www.996.fm/episodes/20vc--ep-18561df4/

## Cold open

**Harry Stebbings** [0:00]:

Today is one of the most important days in the seven year journey of 20 VC. Today starts the next chapter of 20, the media platform that extends well beyond venture, bringing you discussions with some of the world's leading minds across different functional areas of business building. Welcome to day 20 growth, The series that highlights the 10 best growth leaders sharing their thoughts, lessons, expertise, and advice on scaling the highest performing growth teams in the world. For founders hiring and scaling growth teams, this series will provide you a benchmark for how truly great growth leaders think and execute.

## Intro

**Harry Stebbings** [0:32]:

And I could not be more thrilled to have Casey Winters join me for our first episode. Casey is the Chief Product Officer at Eventbrite, where he leads the PM, product design, research, and growth marketing teams. Prior to Eventbrite, Casey spent close to three years at Pinterest where he led the growth product team there. At Pinterest, Casey turned SEO into a scalable acquisition strategy, increasing conversion to sign ups five x. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub's demand side acquisition and retention strategies. Casey played an instrumental role in scaling Grubhub from three cities to over a thousand and from a $1,000,000 series a to an IPO and a $7,300,000,000 exit. And if that wasn't enough, Casey's also advised the likes of Canva, Hipcamp, Reddit, and Faire, just to name a few.

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## Conversation

**Harry Stebbings** [2:39]:

Casey, this is such a joy to do. I can't believe we met in a restaurant in London many years ago now, four or five years ago, but it's so good to do this. So thank you so much for joining me.

**Casey Winters** [2:46]:

Yeah. Thanks for having me.

**Harry Stebbings** [2:48]:

Not at all, but I always love to start with some context. And so talk to me about your entry into startups and how you came to lead some of the most powerful growth orgs really in the world with the likes of Pinterest, now with Eventbrite. How did that come to be?

**Casey Winters** [3:00]:

Yeah. So I actually started my career as an analyst at apartments.com. It was my job to measure the success of all these channels we were using to drive demand, SEO, AdWords, affiliate marketing, email. And these were all channels that were native to the internet. It was not what I learned about in my marketing classes. Naturally from there, as I learned how they worked and how well they were doing, I started working directly on improving the performance of those channels. So I started to think of ways these channels could be more effective. I started to think of ways the traffic could perform better once they landed on our site, you know, and turned into leads, went to focus groups to find out what people wanted, to see how the product can improve. And as I started to combine all this together, I got the feedback from the team, you're this weird marketing and product hybrid, we don't know what to do with that. Because the orgs of product and marketing were super siloed at that time, not just at apartments.com, I think in most companies. So I worked on a lot of entrepreneurial projects at apartments.com, where that combo would be a feature, not a bug. We did a last minute rental product. We did a rental homes product. And we launched a real estate competitor to Zillow, where I ended up running all the performance marketing analytics and biz dev. After a year and a half of working on that was when Grubhub raised their 1,000,000 Series A, and the founders were both apartments.com alums. So when they asked, you know, people in their network who they should talk to about leading marketing there, a mutual friend recommended me. So I ended up joining Grubhub as the fifteenth employee. We did not have the term growth yet, but you would definitely think of my role today as the head of growth where my job is to basically grow the demand side the product. So Grubhub, for those of you not familiar, one of the original food delivery services where you could order online from delivery restaurants, but different from kind of a lot of the things that had today, it was all restaurants that did their own delivery. From the supply side, you know, sales would basically go and sign up restaurants. That was my job to make sure they got orders and they would and therefore they would stick around and we were able to grow the network effect of this business. Basically stayed there from Series A to IPO, you know, scaled out from a couple markets to, you know, most of The US from very tiny Series A valuation to, you know, a multibillion dollar company. So I was there for five and a half years. And as I kind of wrapping up and thinking about what was next, you know, Grubhub was in Chicago. A lot of the action around startups was in San Francisco and Silicon Valley. So I I took a trip out to kind of see if there was like, you know, a next good fit there. And that's when I met Pinterest and, you know, they were looking to build out their growth team. I ended up joining there at the end of twenty thirteen, built out basically new ways to for Pinterest to scalably grow and mainly to make international growth happen because it was primarily a US based business. Know, ended up leading the growth team there, stayed there from about 40,000,000 monthly actives to 150,000,000 monthly actives. Had started advising some other companies around growth like Airbnb and pocket and ended up leaving to join a VC to basically just do that full time. So I became this growth advisor in residence at Greylock. I was working with like 50 plus companies on figuring out their growth strategies and how to scale their businesses. Really what I learned there is that like for most people that are like building a company, it's their first time. They're not sure what's going right, what's going wrong, what's normal, what's abnormal. So I actually ended up leaving Greylock to just advise companies full time. I ended up working with lots of different companies, companies like Canva, Eventbrite, Tinder, Thumbtack on various different scaling problems. You have to doing that for a couple of years. Once I was working most closely with was Eventbrite. They opened the Chief Product Officer role and they asked me to consider it. And I've been doing that for the last couple of years and it's been quite a ride.

**Harry Stebbings** [6:29]:

I mean, there's many things that strike me. I I do love the 1,000,000 series a for Grubhub. I mean, my wife I know. It

**Casey Winters** [6:34]:

sounds like a tiny seed round now. It's cute.

**Harry Stebbings** [6:36]:

Well, I mean, that's like a pre pre seed now. But the other thing that you mentioned that, though, was, like, you know, when you were advising the companies, this is founders first time in a lot of cases. And bluntly, you don't know what you're doing in a lot of cases. And that's why I'm so passionate about doing this series though, which is like bluntly, we need to set a benchmark for what truly great looks like in growth and actually what growth is for founders. And so I think the most important thing and you said, you know, about your Grubhub role, it was called marketing, but it would be defined as growth. If we start on the definition, how do you define growth and kind of VP or head of growth?

**Casey Winters** [7:07]:

Yeah. So and this was something we had to work on at Pinterest, you know, when it was really, like, actually labeled the growth team for the first time. And really what I settled on is growth is about connecting people to the value that's already been created by the business, you know, either through product or services or whatever. So growth is not about building totally new features, totally new products. It's about once we have those and we've confirmed that they have product market fit, that we're doing best job possible at connecting as many people as possible to those products and features that they would find value in. So that's really the key element of growth to me. You know, as a growth leader, think I the most important thing is trying to understand the growth model of the business. So how does this business actually grow? What are the current constraints? And how do we alleviate those constraints? Those might not all be ideas that say a growth team can execute on. As my role as Chief Product Officer, I manage the entire product management team, product design team, the growth marketing team, the research team. And looking through like our growth model, a lot of our constraints are not things that our growth team can solve, right? We need to build out new product functionality, or we need to build out entirely new value props to to ultimately scale the business where we wanna take it. But a lot of the time, especially in network effects businesses, it's just making it easier to find the value or going out and acquiring more people who we know will value the experience. And that's something that growth teams can do really well.

**Harry Stebbings** [8:28]:

Two big things that kind of spring to mind for me is that, you know, you can have a dedicated growth team like you did at Pinterest or like many do, and then you can also kind of integrate it into product teams. How do you think about that decision for companies when you're advising them on whether to have it integrated or whether to have it external? What are the factors that we should consider?

**Casey Winters** [8:47]:

Yeah. So I am default a huge believer in cross functional teams. So the way that we had the team structured at Pinterest is this cross functional team between engineering, product management, design, and analytics. So I actually reported to the head of product. There's actually a time where I reported to the CMO as well. And, you know, my engineering counterpart reported to the head of engineering, etcetera. But we sat together back when you could do that, and we all shared the same goals. We build our OKRs as a unit, you know, across the growth engineering, growth product, growth design, growth analytics, and execute together as cross function team because growth is really a team sport. You're gonna need all these different skill sets to go after the best growth ideas. That's the default state that I would recommend. There is an alternative approach of you have a growth executive that reports directly to the CEO, and they have perhaps their own engineers, their own PMs, their own marketers, their own designers, etcetera. While that can be really good at going fast, a lot of times by going fast, you're not going far, because you're not as default biased to keeping the rest of the organization in the loop with what a growth team is doing. And since growth is a relatively new style of working inside a company, there's a lot of skepticism around whether what you're doing is creating long term value for the company. So I always advise growth leaders that they should spend a lot of time explaining what they're doing, why they're doing it, because the default will be people don't understand or assume it's not valuable. So that's my default stance, because it just makes sure that growth strategy gets infused to the other parts of the organization when my peers or other product leaders, you know, that report to the same person.

**Harry Stebbings** [10:22]:

When do you think is the right time to really start thinking about growing the growth team or starting the growth team? When is that right time?

**Casey Winters** [10:29]:

Yeah. You know, generally, the way I think about it is as soon as possible after product market fit, that's when growth becomes the number one concern of most startups. And that's where you need to be building out that capability. That doesn't mean you necessarily are starting a team. I talked to lot of founders, they're like, oh, I have product market fit, I need a head of My response is like, well, good luck with that, because there are perhaps 50 people that are capable of that have shown previous, like, head of growth experience, and they're not gonna join your company until they've seen that you've already prioritized growth and shown that you value it inside an organization. So when you actually look at how most growth teams are formed, it's usually like an engineer or a PM or designer getting frustrated that something's been utterly left behind by their roadmap and then just going and making it It could be onboarding. It could be the logged out experience. It could be their sharing flows. And then by having some really big success in doing that, they build a team around it. So a lot of the people that you look at that were head of growth were just really early employees that took an interest in that area and then scaled the team around it.

**Harry Stebbings** [11:29]:

So if you're a founder then and you wanna show an incredible hire that you do value growth, what could founders do to show an external candidate that growth is front and center for me now and moving forwards?

**Casey Winters** [11:40]:

Basically, all you do is you show an existing team that's gotten to work and had success and then rewarded for that success. If you've found product market fit, you're starting to scale, you're worried about growth, you've actually put engineers on growth. You've put PMs on growth. And look, it could be one engineer, one designer, one PM, whatever. It doesn't need to be a huge team. But don't wait for me to come in as a growth leader to put resources toward it. Put resources toward it now, show that they're being successful inside your organization, and then say, hey, they need to get to the next level. They'd be excited to bring in a leader that they can learn from. And then, you know, ideally, you get to talk to them through that process. Right? And they can confirm that the company's really excited about growth, about this approach, and that you're not gonna face any huge structural hurdles to success.

**Harry Stebbings** [12:24]:

Let's be hypothetical here. And that's put me in the position of the founder and you're gonna be the adviser to me. And so I've put the prioritization on growth. I've shown with the team that we have that I'm focused on growth. I need to hire that head of growth. Yeah. If you're advising me in this hypothetical situation, how would I literally structure the process of hiring a head of growth? And what would the stages look like if you were to run it with me?

**Casey Winters** [12:46]:

Yeah. Great. I'd say the first thing to think about is when we're talking about growth, how far are we in our process and strategy of driving growth? So, you know, I separate this into Kindle and Fire strategies. Kindle strategies are like, oh, we get the, like, early users. Right? Things are starting to we're starting to see actual usage. And then Fire strategies is, like, really about scale. You don't wanna bring it ahead of growth to start kindling things. You wanna bring it ahead of growth to like really start the fire. While there are thousands of all these bespoke strategies, you know, to companies to get kindling going, you know, whether it's to start your network effect or just get your early users if you're a SaaS business. Fire strategies, there's really only a few of them. Right? You know, you could scale via sales. You could scale via performance marketing. You could scale via content loops, or you could scale via virality. So as I talk to founders about this, I'm trying to understand, are they still kindling? Don't waste your time trying to recruit ahead of growth. You're not gonna be able to do it. But if you're ready to, like, scale one or more of those different types of, like, acquisition loops or engagement strategies, a, let's think about which one's most important because there are specialists and that are better at some of those versus others. And then we could start to, you know, build a process around how big is the team, what type of leader do we want, and how do we, like, test some of the critical skills that matter. And I think there's a few critical skills that you're gonna test for. The most generic one, like, in every single instance of this is going to be, like, really strong capability with data. All great product work is a combination of, like, different sources of data. Right? Whether it's, you know, looking at the raw data that your users are generating or talking directly to your users and talking directly to like your internal teams and like synthesizing all that into a hopefully a great strategic soup. But growth tends to operate on quicker iteration cycles, leveraging a lot of data, a lot of experiments, and you want someone that just default understands how to isolate variables and find the appropriate datasets and instrument. So that's usually like a core skill set that I would ask any growth leader, we can go from there.

**Harry Stebbings** [14:45]:

We're gonna talk about the others. I do just wanna ask. Say we want that as the core skill. And me and you are sitting on this side of the table, we've got our calendar on the other side. I don't know how to test if someone's really brilliant with data. What questions do you ask to tease out whether they have a data oriented mind approach? What would you ask to go deeper?

**Casey Winters** [15:03]:

Yeah. So I have some battle tested questions here, and I I don't feel like I wanna give them away on this podcast. But, you know, the first one that I really do is more of a diagnostic question, which is something to the effect of, you know, you walked in one morning and this metric went down by a material amount. How do you figure out what happened? And then you kinda walk through a a case study related to that. And that's seeing if someone can really think about the variables that would impact a metric going up or down so that they can quickly get to the source of the problem and then, you know, go fix it. I'll adjust that based on the what metrics matter to the business or what channels matter to the business in terms of how I actually ask it. A second one, I would say is a little bit harder, which is, you know, I'd give like a random metric and a random dimension where it is, let's say, oh, okay, well, listeners, the podcasts have gone up a lot on the weekends year over year. How do we figure out the root cause of that? A lot of people will do is they'll do kind of the same approach to that previous question. Right? Where they'll be like, oh, well, you know, I'll look at what countries they're coming from, or I'll look at if like it's happening through Spotify or if it's happening through, you know, people coming directly to our site. That's actually like not the point. The point is that like, well, if you're a startup, like every metric's up year over year. So is there actually a specific trend related to the weekends, or it's just that, like, every metric is up? So the right answer to that question is like, what happened on the weekdays? Oh, turns out it grew the same amount on the weekdays. There's no weekend trend here. Like, go about your business. So there are these different things where it's like understanding base rates, understanding comparative datasets, isolating variables, and being able to do, like, quick diagnostics that are just kinda gonna be core to any growth team role. You're gonna need those no matter what the company is.

**Harry Stebbings** [16:39]:

Can I ask, if we think about the other skills, what are the other ones? If that's, like, the base layer, the data oriented mind, what are the other ones which you look for?

**Casey Winters** [16:46]:

Yeah. So that second one I would say is if there's specific subject matter expertise, you should really only be hiring ahead of growth if you know that there's, like, one specific type of loop that you're trying to scale. Right? Whether it's performance marketing or content or etcetera. So a lot of times you're just testing for how well they already know how to optimize for that channel. You know, if it's in the case of like, oh, it's a user generated content site, we're gonna distribute our content to Google, we're gonna distribute our content through social channels. I wanna see that people understand how the Google algorithm works, that they know how to improve volume of content created, but also the distribution of content created, like something like that. Right? So so that's like a key one. The other is something that I would I'd probably test for any sort of product role, but certainly is more key for growth roles, which is when you think about the different avenues for growth and you put it on like a McKinsey horizons model. Right? Usually, the bottom of that layer cake is product driven growth because it is scalable. Let's say we make a change today that increases our conversion rate by 5%. It's gonna convert 5% better today, tomorrow, a year from now, maybe even five years from now. Right? So if it works, it continues to work. It's measurable. You can run an experiment and understand that it is 5%, or at least once you get to a certain scale, you may not be able to do that at a super early stage. And if you wanna do more things like that, it just scales with building out the team, building out engineers, building out designers, etcetera. The next layer of that cake is usually performance marketing, like some paid channels. And it's fundamentally very similar to product driven growth in that it's scalable, it's measurable, it just scales with budget. You're gonna spend a lot of money on it. And then that third layer of the cake is brand marketing, which is neither measurable nor scalable and requires money. It's not a bad idea. It's just usually has a longer return, a more speculative return. So generally startups wait longer before they invest in that. Right? So where are you trying to optimize right now? And for some of the time, like, let's say you're a consumer subscription company or direct consumer e commerce, it just really is a performance marketing game. You want someone that knows Facebook and Google inside and out, and like, you just wanna, like, really know that you're bringing in someone that not only knows it super well, but could teach a broader team it. But for a lot of these companies, it's gonna be more focused on like the product side. So let's assume you're working on product driven growth. A lot of what product driven growth requires is someone that can figure out a grand opportunity and then break it down into really small chunks that help them learn. That they're not, you know, putting forth a six month project, they're putting forth a one week project that lets them know if they're getting enough value to continue. So I've designed a bunch of questions, you know, in the past where it's like, hey, we have this feature. Could we leverage it for growth? Okay. Hey, like, does the feature, like, improve retention or engagement, right, or monetization? Where else would you try to leverage that feature to get more people to use it and see if people can structure an experiment that doesn't take a whole lot of time that actually would get them some key answers or some key growth? Those would be, like, the types of, you know, questions I try to answer.

**Harry Stebbings** [19:40]:

In terms of, like, case studies to tease things out of people, you know, I was chatting to a young founder the other day and he said, you know, I'm using you as an example here, but, you know, I wanna hire Casey as my head of growth. But Casey's got so pedigreed and, you know, respected and, like, I can't ask him to do a case study. Like, he's gonna laugh me out of the room as a little startup and you want me to do a case study for you. Like, alright, mate. Is that wrong to ask people to do case studies if there is that kind of imbalance young startup to respected growth leader? How would you advise them?

**Casey Winters** [20:09]:

I don't think it's inappropriate. I just think it's there's a timing of when it makes sense. Right? So, you know, for founders, a lot of their recruiting of executives can take a long time, a year or longer. Right? Like, I advised Eventbrite for two years before, you know, I joined full time. And in a lot of cases, like, if an early stage startup wants to hire someone like me or someone like me, maybe five years earlier in my career or whatever, it is too They don't need that skill set yet. They may need it in a year or two or three years. A lot of recruiting for founders is just building relationships with smart people. And then, you know, there might be, you know, a time where you can put a ring on it later down the line, or they become an advisor and that's it. So I just urge founders to, like, meet as many smart people as you can. Try to hire some of them, but try to keep the ones you can't hire close because maybe you can hire them in the future. But if there is kind of a process, right, once I'm in and, like, look, I wanna be considered for this role, then it's the duty of both sides to try to understand what is a process we could devise where both of us get the right level of information to understand if the role and company is right for both of us. Right? And what happens with a lot of executive hiring mistakes is there becomes this excitement between, you know, the two of us per se about working together that we don't really do the work to say, like, well, Casey, here's really what I need day to day. And then, you know, I come in and then there's a misalignment, right, of like, oh, this is this job isn't what I expected. Or, like, like, I just don't actually have the skills you need. Right? It's not necessarily interest. It might be like capability. So you wanna get at that as soon as possible once you know that the candidate's super in. So it becomes like it's sell, sell, sell. Once they're interested, it'd be like, hey, I have a duty to show you what this job is. Let's do a little bit of it together and make sure you wanna do it and that you like it.

**Harry Stebbings** [21:47]:

I like that as a phrasing. It's almost I'm doing it for you, but you're actually getting the information as the founder.

**Casey Winters** [21:53]:

Yeah. I mean, you know, interviews should be for both sides. Right? If I feel like that case study is beneath me, that's a problem. That means I'm probably not a good fit for the job right now, and you should be hiring someone more junior. Right? Yeah.

**Harry Stebbings** [22:03]:

No. I agree. Okay. So let's say, you know, you've advised me brilliantly well. We found our incredible head of growth. My hypotheticals got up. What are the first few weeks that, like, I've never worked with anyone in growth before? How do I make onboarding as effective as possible?

**Casey Winters** [22:17]:

Yeah. I would say in general, onboarding is not great inside startups. You know, when I think about starting this at, you know, Grubhub and Pinterest, I spend so much of my time in the data, you know, writing SQL queries, trying to understand where does traffic come from, what does conversion look like, what do our cohort retention curves look like, are there any differences, you know, in different types of users. You wanna carve out a decent amount of time where, you know, this person can understand the data model, like what data you're capturing, how you're capturing it, and that they can just go nuts in trying to build, you know, usually their own process of understanding the business through, you know, certain dashboards or, you know, Google sheets or whatever. And so that's a material part of it. And the more that you have someone already at the company that can walk them through that or kind of show the dashboards, etcetera, that already exist, you know, obviously the better. I joined early enough at Grubhub and Pinterest where usually that stuff just didn't exist, I had to go build it myself. But startups are better at this now. You know, they're more sophisticated. They might already have, you know, segments set up or mode or whatever, and are looking at some of the right metrics already. So that's usually a big part of it. Another big part of it is setting this person up to actually meet like real customers so that they can truly understand the core value that customers find in it. Because if our job as like a growth leader is to connect people to the core value of the product, We need to understand that core value almost better than anyone at the company. We need to know how to talk about it. We need to know the steps that get them introduced to it most effectively. That is a key element that I think a lot of growth teams miss. Right? They just think it's a data game and it's an experimentation game. And then it's like, when's the last time you talked to an actual user? And they can't tell you. Like, that's a big problem. Growth leaders need to be talking to users all the time. Know, and back to this thing we talked about earlier, building relationships with the broader team is super important because there still is this default skepticism of growth work inside of a lot of companies because just people don't understand it. We've all experienced, like, spammy stuff from other companies in the past. So you wanna go be starting to build that trust with all of these other leaders. Let's say I came in as a head of growth and there is a separate head of product because and usually the the reasons you would do this is that, especially in non network effects business, a lot of times you might find product market fit, but there's still a whole lot of product that needs to be built out, which means your head of product will never spend an ounce of time thinking about growth. And then you'll hire a peer instead of hire you know, instead of build that cross functional team approach I talked about earlier. In that case, even so, you gotta have a very close relationship with that head of product. Right? You need to be aligned, and it basically needs to feel like, oh, this head of growth is making sure more people use my stuff. That's amazing. I wanna set him up for success instead of this head of growth is building things that sacrifice the quality of the overall product experience or, you know, spams people or whatnot. So building a lot of those relationships with, you know, other executives, peers, individuals is super important.

**Harry Stebbings** [25:01]:

I'm too intrigued. You said there about kind of the integration of product and growth in that kind of difficult relationship. How do you think about removing the element of growth just come in, fuck with my code, and then sod off, which some product people do feel. How do you think about that? Remove that. Reduce it. Having had the experiences you've had.

**Casey Winters** [25:20]:

Yeah. So, I mean, that was definitely the default state at Pinterest when I joined. Right? The growth team had a lot of skepticism from people that weren't on the growth team. So I would say I made, like, half of my job communicating what we were doing and why to the rest of the organization and swarmed on any skepticism that would occur. So, like, for example, we would have, like, new people come in to the company all the time, and they would be like, this growth experiment is bullshit, whatever. I would immediately schedule a one on one with them. I would walk them through why we did it, get their feedback on it, make sure they understood. And then if they have skepticism in the future, they'd be like, I know Casey. He's a human being. You know, he's a nice guy. I'll give him the benefit of doubt and I'll ask him what's going on instead of like, just assume there's bad intention. So I see this with a lot of growth leaders, especially if they're independent, but can still happen even if they have more of the cross functional model I talked about earlier, where there's not doing enough job, you know, preaching the gospel of growth and why this is ultimately valuable for the company. That needs to be a significant part of the role. And look, you might have a situation where like you have a Zuckerberg that so bought in that, like, he'll do that work for you. But in most cases, the founders figure this out too, and they'll listen to you. They'll listen to other leaders of the company. They don't know what's right. Like I said, they're figuring it all out. I see a mistake a lot of executives make, and this is outside of growth too, where they're like, they'll expect their manager or the CEO to like take care of their problems for them. And it's like, no, that's not what happens. Like, you gotta go solve those problems yourself. You gotta go build those relationships. You gotta explain why you're doing what you're doing. If you screw up, go admit it and explain why and why it won't happen again. That's a huge part of the role that people underestimate, especially for growth.

**Harry Stebbings** [26:56]:

Can I ask, when you think about that relationship with the CEO, say, you know, we've hired the CEO and you're advising me again on this relationship? Should I have weekly meetings with him? Should it be one on one? Should it be with the growth team? How should I structure our communication, and what should that communication look like in an ideal world?

**Casey Winters** [27:12]:

Yeah. It's funny. It reminds me of a story at Pinterest where, you know, we had a cross functional team on growth. We had cross functional team on monetization, and then we had, you know, cross functional teams on, like, our core value props as well. Jack, who was our head of product at the time, we were having like a product team meeting and he was like, Hey, all of you are going to product review too often to try to get in front of Ben, our CEO and talk product and talk shop. And look, Ben enjoys that, but like, go build, like, don't spend so much time in product review. And he was like, except Casey, you should probably go to product review more often because, you know, we had gotten in a rhythm of like moving metrics to the business and there was default kind of trust there. So basically what I was doing as I was coming in every quarter and communicating our results on our OKRs, what we learned and how that would feed into what we were going to work on, you know, the next quarter or so. That was kind of all I was doing. I don't think that's enough, but it depends on the CEO. Right? So Ben, in that case, visionary product founder, Evan as well, our other co founder, visionary product founders, they are going to naturally spend more of their time thinking about how the core product evolves, rather than thinking about how can I move this metric up 2%, 5%, 10%, etcetera? For me, I kind of saw that as like, make sure they understand the strategy clearly, make sure they understand the metrics clearly, and then go back to work. But we all work at the pleasure of, you know, our CEOs. It's their company. It's not yours. What a lot of product leaders make a mistake of as well as growth leaders is they think it's their show. They get to create the vision. They get to create the strategy. And it's like, not really. You're there to execute on the vision and strategy of the founders. And you wanna get really clear about what they're gonna say, just do. I want this to happen versus what you really get to bottoms up develop yourself. And it's never gonna be a 100%, you know, either way. But this is a big issue with like a Chief Product Officer role a lot of time is someone comes in, think they they'll be able to create the product strategy and envision themselves. And then it's like, oh no, no, you're actually there to make sure that vision that's already in the founder's head gets executed better. And there might be some parts of it you don't like, but guess what? It isn't your company. You wanna like, kind of feel that out. Like in the case of Pinterest, they're a little bit more hands off on the growth strategy. Like, as long as I was delivering the results, cool. And then there were some times where that changed. And, you know, I had to kind of shift the strategy based on some really strong points of view from our founders. But I do think you wanna meet more often than I was doing with Ben.

**Harry Stebbings** [29:25]:

Yeah. I mean, I think that's a little bit light. I do have to ask you, mentioned kind of, you know, if everything was going well, great. And it's it's kind of like that kind of within companies, but you feel it especially, I think, within growth teams. When things are great, we are killing it. Yes. We are the best growth team. And when things are bad, I mean, it must be tough. Right. Right. As a growth leader, how do you keep teams level when things are actually very volatile in terms of morale internally?

**Casey Winters** [29:50]:

Yeah. So, I mean, you know, if you look at these companies from the outside, you see this consistent up into the right graph of every metric, but that's because the graph is really zoomed out. Like, if you zoom in, there's a lot of, you know, ebbs and flows going on. I think the main thing, you know, and this is both for managing the founders as well as managing your team. You can't focus entirely on the results, what you really wanna focus on is the learning. Are we continuing to learn how our users operate, how this business operates, and what our scalable growth strategies are? As long as that learning loop is quick, that's gonna translate into results. The flip side is if you celebrate results, lot of times you don't have anything to do with them. I remember when I started, you know, on the growth team at Pinterest, Basically, what happened at Pinterest is a lot of our core loops stopped working. We were initially a direct network effect business where you connected with your friends on Pinterest through your Facebook account. You saw the things that they shared and that created engagement. And then when you pinned anything, we would share it to Facebook and that's how new people would find it and then join the service. When Facebook changed the way the Open Graph worked, all of a sudden we stopped getting any new users. And also, as we started to expand beyond, you know, Midwestern moms who were the original core audience to people who had different tastes, that friend model of seeing great content started to ebb in engagement. Like if your girlfriend joined the service and then she invited you and you only saw things that she was pinning, that may not match your interest super well, and you would think that the service wasn't for you. So we had to basically do this open heart surgery on basically the core engagement loop to move away from a friend based graft to a topical based graft and to move away from Facebook distribution to Google distribution. And growth was not great during a lot of those times, but it's keeping people to have understanding of our strategy, where we're going, why it's valuable, and are we learning the right things to ultimately make that new strategy successful? And we ultimately did make both of those pivots super successful. And that's now the core acquisition and engagement loops that continue to drive, you know, Pinterest today, six years later or whatever. But there are times when, yeah, growth looks really terrible. We weren't just only looking at that. We were looking at if we were advancing our strategy to eventually have that very scalable growth strategy, which now the company does.

**Harry Stebbings** [31:55]:

You said there about kind of some of your, you know, lessons and journeys from Pinterest in particular. I'm really interested. When you think back over your career, can you talk about a growth decision you made without data to back it up? How did it go, and what were some takeaways for you?

**Casey Winters** [32:08]:

Yeah. So it's funny. Every growth experiment I recommended when I joined a company, I'm fundamentally using more of my gut from previous experience. Right? Every time that has not worked. Like, when I remember, like, the first thing I tried at Grubhub, failure. It was trying to set up some some affiliate marketing relationships that I had, you know, built out in the past. Didn't work. When I started at Pinterest, I tried to do some internal linking work for SEO. Didn't move the needle at all. Fundamentally, I think the data is the core of finding good good ideas. Usually when I'm not, then it doesn't work super well. I'd say one that was more of a strategic shift for us at at Pinterest was one of the things we did, which we've taken a lot of flack for is when people came in from Google, we would let you see a preview of the content, and then we would ask you to sign up to see more of it. Because if we didn't, people would just look at content from Google, and then we'd never see them again. And then they never get connected to the true value of Pinterest, which is like, you know, getting better recommending you content related to your interest. So as we did that, that was really successful. And we ended up signing up, you know, like over half of The US up to Pinterest with, you know, a pretty high retention rate. But when you move into, you know, the second half of the population or the second half of the adult population, you're now moving into a different state of the product adoption curve. You're meeting kind of that late majority and laggards. And those people, you know, typically need more convincing to sign up for anything and to stick around. So we entirely shifted our acquisition model based on that kind of strategic understanding, but not based on like a, you know, an experiment that told us anything to try to open it up for those people, start to get a sense of the different things they were interested in, and then recommend them eventually to join Pinterest. And that was based on more of some intuitive understanding rather than, like, the data we were seeing. That did not work super well either. So my track record of, like, not leveraging data and being successful with things that drive growth of the business is is not good.

**Harry Stebbings** [34:00]:

I love that. Is it tough though in the way that, like, you can try things and they work once with one company? It's like an investment, you know. If you have success in consumer social, quite often you think, wow. Consumer social's great and I wanna do more. And it was just one good investment, like, one good environment. Is it tough to not let future decisions be impacted by past successes or failures?

**Casey Winters** [34:20]:

Well, I think the mistake that a lot of people have made in the growth world is I did this thing at this company, it worked, therefore this thing works. Instead of doing the next step, which is like, well, why did it work here? And in what other context will it work versus potentially not work? Right? You know, a lot of these differences are based on the type of business you're in. Right? So like b to b SaaS versus a marketplace versus like a consumer social company. There are different things that tend to be successful, and there might be some primitives that are causing that. Right? Like intent to the user. If intent to the user is high, you can do all this stuff. Intent to the user is low, you kinda need to do the opposite. Right? What I really try to do is build frameworks that are battle tested across many different models and stages of company before I'm, like, really certain that, like, you should do x thing. Because so much of this is context specific, and so few people in the startup community know even which context they're in. So they might, oh, I read Facebook does it this way, and it's like, great. You're an enterprise SaaS company. What Facebook does has, like, no material impact to your strategy at all. Like, it couldn't be a more different business. Right? But unless you, like, explicitly call that out to a founder, won't, like, piece those two things together themselves a lot the time.

**Harry Stebbings** [35:25]:

I know. I'm totally with you. I do wanna touch on one final thing before the the quick fire. I could chat to you all day about this. But it's like, you know, you angel invest now and you have made some great angel investments. How is the investing as an additional hat? How has that impacted or altered your mindset towards growth and really kind of company building?

**Casey Winters** [35:43]:

Yeah. So when I think about, you know, joining companies in the past or even like a lot of the companies I've advised, it was really about confirming that there was already super strong product market fit, and then I can help them take that product to as many people as possible. Whereas in a lot of the investing game, you're dealing with companies like a little bit earlier. They might not be sure if they have product market fit yet or definitely are still figuring it out. Part So of the question for me is like, should I work with those companies at all or not? And I think the answer is like sometimes, especially if it maps to like, you know, some of my previous experience, which is user generated content in marketplaces. So really what I've had to do is build my own framework on what product market fit looks like, you know, how we get there if we're not there yet, which is not something, you know, I had done much previous in my career. And the other element is the difference in kind of being the owner versus being there to advise. Because, like, whether you're advising or you're investing, like, you can't go own that problem. You can't say, like, well, I know how to figure that out. Therefore, the company should figure it out. Like, if you're investing, a lot of times, it's like, well, I can give some counsel, but can they really pull this off themselves? Not can I jump in there and do the job full time because I'm not available to that? It's like, are they gonna be able to figure this out themselves? So that's kind of a a difference in kind of the the structure of, like, you can't go solve it for them. You might be able to point them in the right direction, but they have to run that direction. Yeah. And then, you know, the other is, like, in other companies, like, I could rely on my rate of execution, you know, like, my speed, my learning loop, but now it's become this different element of I'm really trying to gauge how quickly they learn, how quickly they execute. And that's, like, the the biggest factor. And how do you do that, you know, as part of, like, a lot of the networking that is angel investing is something I'm still trying to figure out.

**Harry Stebbings** [37:21]:

I'm totally with you, but I love it. It's such a good additional hand. I think you learned so much additional from doing it. I do wanna move into my favorite though, Casey, which is the quick fire. So I say a short statement, and then you give me your immediate thoughts. Does that sound okay?

**Casey Winters** [37:33]:

Alright. Let's do it.

**Harry Stebbings** [37:34]:

Okay. So what tactics have not changed in growth over the last five years?

**Casey Winters** [37:38]:

I would say SEO has been pretty stable as a platform, email also. AdWords has had a little bit of change, especially on the mobile side, but all in all, a relatively stable channel.

**Harry Stebbings** [37:49]:

Okay. What tactics have died a death, which was super hot and now super not?

**Casey Winters** [37:54]:

Generally, anything organic social related just doesn't exist anymore because the social networks are so good at taxing any reach that you wanna have on the social channels. So that's one that feels relatively dead. And then there was a time where a lot of, like, consumer SMS was a big thing, and that channel got burned pretty quickly as well. Clubhouse is really the last one that's had any success with any, like, invite related things, but that was, like, super hot for a while. And then everyone was like, no, I'm not gonna, like, spam my friends with SMSs. That one's definitely cooled off a lot too.

**Harry Stebbings** [38:25]:

What would you say is the biggest mistake founders make when hiring growth teams?

**Casey Winters** [38:29]:

I think picking the wrong metric to focus on is super common. And, you know, I try to make sure founders are picking an activity metric that best correlates to value being experienced at an appropriate level of frequency. Like, how often do you expect people to experience that value? But there's so many people that are optimizing for MAU when it doesn't make any sense or for GMV when, you know, that's not really the right signal. So that's a big problem. The other one is just optimizing only for short term. Like, you're ultimately optimizing for how stable the company is seven to ten years from now. Right? So optimizing only for metrics that are gonna look good for a fundraising deck or over the next quarter, a lot times ain't the right call.

**Harry Stebbings** [39:06]:

What one piece of advice would you give to a growth leader today starting a new role?

**Casey Winters** [39:10]:

I think it's this concept of spending as much time as you can communicating what you were doing as much as the what you're actually spending your time on to grow the business. Because there's still that lack of understanding of growth strategy that, you know, people like me are working on changing across the industry, but it's just more nascent. So really managing those relationships and communicating the why is the thing that I find most growth leaders under invest in.

**Harry Stebbings** [39:32]:

What would you most like to change about the world of growth?

**Casey Winters** [39:35]:

This concept of growth hacking. I hate the term. First off, growth is done in a team, and it's not just hacks or experiments. Like, it requires understanding the growth model of the business, where the constraints are, and potentially doing quick hacks. But a lot of times, deep engineering work to to actually scale the business. That one's definitely an important one. I'd say the other one is just like the default towards performance marketing is the only channel that matters. It creates a lot of issues long term, especially if you're not network effect driven where it's gonna work really well in year one, not as well in year two. And in year five, you're underwater. Because it's quick, that's a lot of the ones that everyone goes to and it, yeah, creates some problems down the line.

**Harry Stebbings** [40:13]:

Tell me, my friend, final one, what one company growth strategy have you been most impressed by recently other than Eventbrite?

**Casey Winters** [40:21]:

Yeah. I'll talk about my book a little bit. So a couple of the companies that I've advised, part of the reason I started advising them is because of how impressed I was with how well they were doing on this. So Faire is a a b to b wholesale marketplace. Been really impressed with how they get both sides of the market to invite each other into, you know, the superior way to transact. Canva is, you know, a company that on the outside looks like more of a consumer subscription company, but it's able to grow like a network because of all the amazing content that's created through the service. Really, really impressive group. And then Ritual is a company I work with in Toronto. You know, they definitely have hit on some hard times due to COVID, but they essentially are an order ahead app for, you know, coffee shops and lunch places. You could think of it like the Starbucks loyalty app for every other place around you. Just super impressive with how well they understand, you know, their core acquisition loops and how to, like, tune them faster, whether that's through promotions or loyalty points and their speed of execution. So those would be a few that jumped top of mind for me.

**Harry Stebbings** [41:22]:

Casey, this has been so much fun. Honestly, I can't thank you enough for unveiling all the secrets, but, really, this has been awesome. So thank you so much for joining me today.

**Casey Winters** [41:30]:

Yeah. Thanks for having me. It was fun.

**Harry Stebbings** [41:33]:

And there we have it, the first from 20 growth. This will be a monthly show where we have the best growth leaders in the world, and we will feature the 10 best growth leaders to provide that benchmark for you of what truly great looks like in growth. But before we leave you today,

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