The Exchanges

Q others. I do just want to say we want that as the core skill and me and you are sitting on this side of the table and we've got our candidate 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?

A Yeah. So I have some battle tested questions here and I don't feel like I want to 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 walk in one morning and this metric went down by a material amount. How do you figure out what happened? And then you kind of walk through 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 podcast 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…

AI assessment note: “the first one that I really do is more of a diagnostic question”

Q 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?

A Yeah. So, and this was something we had to work on it 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, I think 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. You know, as my role as chief product officer, I manage the entire product management team, product design team, the growth marketing team, the research team. In 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 bus…

AI assessment note: “growth is about connecting people to the value that's already been created by the business”

Q 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. As a growth leader, how do you keep teams level when things are actually very volatile in terms of morale internally?

A Yeah, so I mean, you know, if you look at these companies from the outside, you see this consistent up and to 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 want to 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 going to translate into results. The flip side is if you celebrate results, a 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 to 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, …

AI assessment note: “You can't focus entirely on the results. What you really want to focus on is the learning.”

Q 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?

A 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 like 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 work 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 could improve. 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…

AI assessment note: “I actually started my career as an analyst at Apartments.com.”

Q 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?

A 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 a lot of founders, they're like, oh, I have product market fit, I need a head of growth. My response is like, well, good luck with that, because there are perhaps 50 people that are capable, that have shown previous, like, head of growth experience, and they're not going to 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 better. 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 a team around it.

AI assessment note: “as soon as possible after product market fit, that's when growth becomes”

Q How do I make onboarding as effective as possible?

A 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 want to 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. 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, et cetera, that already exist, you know, obviously the better. I joined early enough at Grubhub and Pinterest where usually that stuff just didn't exist, and 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 per…

AI assessment note: “You want to carve out a decent amount of time where, you know, this person can understand the data model”

Q How did it go? And what were some takeaways for you?

A Yeah. So it's funny. Every growth experiment I've recommended when I've joined a company, I'm fundamentally using more of my gut from previous experience. Every time that has not worked. What I remember, like the first thing I tried at Grubhub, failure. It was trying to set up some, some affiliate marketing relationships that I, 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 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'd never get connected to the true value of Pinterest, which is like getting better at recommending you content related to your interests. So as we did that, that was really successful. And we ended up signing up, you know, like over half of the U S 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…

AI assessment note: “Fundamentally, I think the data is the core of finding good, good ideas.”

Q 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, pfft, alright, mate. Is that wrong to ask people's two case studies if there is that kind of imbalance young startup to respect a growth leader? How would you advise them?

A 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 early in my career or whatever. It is too early. 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. Cause 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 want to 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 in 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…

AI assessment note: “I don't think it's inappropriate. I just think it's, there's a timing”

Q But you said there about kind of some of your 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?

A Yeah. So it's funny. Every growth experiment I've recommended when I've joined a company, I'm fundamentally using more of my gut from previous experience, right? Every time that has not worked. Like, what I remember, like, the first thing I tried at Grubhub, failure. It was trying to set up some, some affiliate marketing relationships that I, 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'd never get connected to the true value of Pinterest, which is like, you know, getting better at recommending you content related to your interests. 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. When you move into, you know, the second half of the …

AI assessment note: “Every growth experiment I've recommended when I've joined a company, I'm fundamentally using more of my gut”

Q I know. I'm totally with you. I do want to touch on one final thing before the quick front. 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 has the investing as an additional hat, how has that impacted or altered your mindset towards growth and really kind of company building?

A 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. Right. 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. So part 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 and 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. Cause 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 th…

AI assessment note: “really what I've had to do is build my own framework on what product market fit looks like”

Q the advisor 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. If you were 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?

A 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 want to bring it ahead of growth to start Kindling things. You want to 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, you know, 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 going to 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, you Let's think about which one's most important because there are specialists and that are better at some of those versus others. An…

AI assessment note: “then we could start to, you know, build a process around how big”

Q 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?

A 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 You know, he's a nice guy. I'll give him the benefit of the 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 it can still happen even if they have more of the cross-functional model I talked about earlier, where they're just 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's so bought in that, like, He'll do that work for you. But in most cases, the founders figuring this out too, and they'll listen to you. They'll listen to other leaders at 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 got to go solve those problems yourself. You got to go build those relationships. You got to e…

AI assessment note: “You got to go build those relationships. You got to explain why you're doing”

Q 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?

A Yeah, so that second one I would say is if there's specific subject matter expertise, you should really only be hiring a head 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 et cetera. 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 going to distribute our content to Google. We're going to distribute our content through social channels. I want to 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 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 five percent…

AI assessment note: “that second one I would say is if there's specific subject matter expertise”

Q 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?

A 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. Well, you know, Jack, who was ahead 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 of 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 with 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 one, two percent, fiv…

AI assessment note: “make sure they understand the strategy clearly, make sure they understand the metrics clearly”