The Exchanges

Q very kind of you, but I do want to start with a little bit on you. So tell me, how did you come to lead some of the most powerful growth orgs, and yes, I have had many coffees before this interview, how did you come to lead some of the most powerful growth orgs with the likes of Instacart and Instagram, What was the entry to growth for you?

A Yeah, it's an interesting story. You know, mine was kind of a classic, in some ways, Silicon Valley experience. I did my own startup in 2011. It was an early competitor to what is now Trunk Club and Stitch Fix. So subscription e-commerce, right time, right vertical, maybe wrong strategy. I didn't do so well, admittedly, and, you know, ended up having to close down after a couple of years. And it kind of fueled me. It fueled me to really understand kind of like, well, what makes these startups work? How do you grow these startups? How do you actually, you know, once you find product market fit, how you make them take off? And so fast forward a couple years later, I ended up at Facebook. This is about spring of 20 14. And when I joined Facebook, you know, I was, I think, one of a hundred PMs at that point. The company was only 6000 employees and they were still hiring in these kind of generalist pools. Let's see the generalist pools. They would just like hire a PM and then you had to go and find a team. But I just kind of happened to hit this slow spot in hiring. So I was like the only PM hired for like six weeks and there was like 15 jobs open. So I was like, well, let me just go and talk to a bunch of these Teams. And, you know, I thought I would only be at Facebook for about a year and a half or so. And so I figured I wanted to learn something that was really tangible. So I fi…

AI assessment note: “I figured I'd either learn the growth or monetization, and I joined the Facebook growth team.”

Q a decision there, which bluntly you got wrong, and Kevin was right. If you think back to the many decisions that you have got right, and it doesn't have to be without data this time, but the many decisions you have got right, which one are you most proud of? You can have a brag session there. Which one are you like, I nailed this one, and I was smart.

A I nailed this one, and I was smart. What was the thing that I'm most proud of? This is a good question. I'd say one of the things that we actually nailed, which I'm pretty proud of, but it's probably actually a little bit controversial now is the kind of the concept of like leaning into multiple accounts at Instagram. You know, the reason why I say this is because when I was there, we had a team that was responsible for what I call access churn. Access churn was basically you Harry are in Instagram. You sign out for whatever reason, right? Like you just don't want background data. You want privacy. And we started seeing that just a ton of people, hundreds of thousands of people a day who would never get back into their account because they forgot their password. So we fixed that, which was actually a massive win. But what we learned was that in fixing it, we saw a bunch of data and we're like, wait, now that we get people back into their accounts, we're actually starting to see content production go up. And we're starting to see engagement go up. And we're starting to see all these other kind of knock-on effects that we had no understanding of why this was happening. And so we kind of like leaned in and said like, We need to figure out why this is happening. We devoted, like, a roadmap to just, like, understanding what was happening, and what we realized is that, like, the peop…

AI assessment note: “the concept of like leaning into multiple accounts at Instagram”

Q What is the optimal onboarding process look like for a growth rep or a growth leader? How should we structure it, and what has it done well?

A I think it's like a listening tour, plus a little bit of a data tour, I'd call it, plus, like, customer conversations. You've got to learn the business, right, and learn really what makes the business tick, and understand what Your cross-functional stakeholders are saying, especially in marketplaces, because, you know, you need to understand, like, what's happening on both sides of business. And then also, you know, does the data really support this or not? Or do you even have enough data? Do you even have clear enough data to actually make any informed decisions? And then talking to customers and understanding, like, what they're saying and, you know, is their feedback make sense? Ultimately, what you're looking for is you're looking at what to, like, push the team forward and say, here are the bets that we need to start making. And, you know, what you're trying to do is just get context as fast as possible.

AI assessment note: “listening tour, plus a little bit of a data tour... plus, like, customer conversations.”

Q In terms of that relationship, how do you know whether to hire a growth engineer, and, you know, and maybe someone more junior in growth, Or bluntly, are you, Casey Winters, Elena, and have a growth leader? How do you know whether to start senior or start junior?

A Yeah, I usually actually tell people to start junior. The reason why is a couple things. One is, you know, when you hire people who are more senior, they tend to be really, really good at, like, understanding systems, building for scale, like, helping to enable teams in order to really, like, kind of get you through crazy scales of growth. But, If you're starting, if you're early stage, what you tend to need is like one person who's really good at your core mechanic. If you are a, for example, an SEO led business, and that's going to be your flow, like hire a world-class SEO person who also understands content marketing, right? So they have a little bit of like growth and they can also like room to grow, but you want someone who can really execute on the top, like thing that's going to move your business and move into adjacencies relatively easily, and then see if you can help them to scale themselves to being that kind of Big growth leader over time.

AI assessment note: “I usually actually tell people to start junior. The reason why is a couple things.”

Q Say we find this incredible growth leader. Thank you for helping me hire him. Great. He's coming in or she's coming in. For the first month, onboarding. What is the optimal onboarding process look like for a growth rep or a growth leader? How should we structure it, and what is it done well?

A I think it's like a listening tour, plus a little bit of a data tour, I'd call it, plus like customer conversations. You've got to learn the business, right, and learn really what makes the business tick, and understand what your cross-functional stakeholders are saying, especially in marketplaces, because you don't, you need to understand, like, What's happening on both sides of business? And then also, you know, does the data really support this or not? Or do you even have enough data? Do you even have clear enough data to actually make any informed decisions? And then talking to customers and understanding like what they're saying and, you know, is their feedback makes sense? You know, ultimately what you're looking for is you're looking at able to like push the team forward and say, here are the bets that we need to start making. And, you know, what you're trying to do is just get context as fast as possible.

AI assessment note: “I think it's like a listening tour, plus a little bit of a data tour”

Q If things are not going as planned, or it's not what you thought it might be for me as the CEO, how long does one give growth reps? How do you think about enough time to Allowing to prove themselves, but also not waiting too long. How do you think about that balance?

A I mean, this is a hard question. It's a frequent one. I have a, maybe a little bit of a controversial opinion here. And my controversial opinion is that great growth isn't built overnight. People, I think, are very antsy, and they want to see, like, kind of, like, see change. And see change doesn't happen overnight. Like, you know, it's always one of these things where, you know, Instagram, we were the fastest growing app in the world when I was there. And, you know, we grew basically 50% year over year for the first couple years while I was there. But, you know, we didn't even start making a dent into our numbers until like month four or five after I joined. That was worth a ton of data, right? So we actually knew where to make bets. And so, you know, sometimes it takes six to nine months to really start making progress if you don't have the right foundation. Now, it depends on what the company is. So when I say the right foundation, meaning like, do you have data logged? Even at the best companies, like when I joined Instagram, we literally did not have logging for all of the registration flow. It was incredible. We knew how many people started and how many people ended, but we did not know what was happening at every step of that flow. Right. And that's like a world-class company that was owned by Facebook at the time in 2016. And so like, you know, if you don't have the dat…

AI assessment note: “sometimes it takes six to nine months to really start making progress”

Q Can I ask, in terms of that, like, communication pathway, what's the right ongoing communication between the head of growth and the CEO and the leadership team? What is that? Is that a monthly check-in? Is that quarterly? How do you think about optimizing the CEO and the head of growth relationship?

A Like, I think it requires lots of communication, lots of transparency, lots of trust. I've never done it where it was less than once a week conversation, even if it's like 30 minutes here and there, because growth numbers change so much so quickly. There's so much demand for understanding kind of like how is the business moving that the ability to really stay aligned Around kind of like expectations, managed expectations and outcomes is critically important. What's also really important, especially the earlier on in the business you are, is really understanding the founder's vision and intuition to help inform growth bets, right? The earlier you are, the less data you have, and the more you need to lean on, like kind of qualitative stuff that you're seeing in the product or from customers or, you know, kind of the vision of the founders, because they will help to inform what you invest in. Whereas later on, when you have a lot more data, it's a lot easier to build roadmaps With really, truly bottoms up and data informed, and like, are actually right more often than not.

AI assessment note: “I've never done it where it was less than once a week conversation”

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

A I think some of it is honestly the, how we talk about ourselves, the transparency about what we do. You know, Facebook created their first consumer product growth And they never really kind of took the lead in like talking about like what makes consumer product growth work well. So I think you still find there's a lot of people who think that growth is really about like dark patterns and just like tricking people into doing things and just like crazy tactics to grow at all costs. When in reality, it's a very thoughtful and very hard discipline, but no one really understands kind of all that goes into all of the models. That transparency about what we do would be great.

AI assessment note: “how we talk about ourselves, the transparency about what we do”

Q How do you think about the fundamental question, which is, do I have an isolated growth team, or do I have a growth team incorporated within my product and tech team?

A One, growth is always cross-functional, right? It should never be on an island, and this is a big, I think, mistake that founders make. It's like, oh, let's just go build a growth team and put them on an island, they'll be okay. You know, oftentimes, you know, you'll have growth will touch products, and it doesn't make sense, for example, for a growth team that's working on product to not talk to the product team, because the product team is working on deepening the engagement, and the growth team is just working on getting more people into the door and getting them better activated. So this is all one customer journey, and so this should be kind of functionally working all together, just like working in different stages of the customer journey, right? And so likewise, if you're doing it from a marketing perspective, The performance marketing team is needs to go work hand in hand with the brand team because the brand assets are going to help to constantly evolve the audience that the performance marketing team can reach. And so I think you have to kind of figure out how they connect and not think of a more online island. I think the question becomes, where do you house growth? And then like, how do you make sure that it feels like integrated and it feels like aligned with the, like the spirit of the business?

AI assessment note: “growth is always cross-functional, right? It should never be on an island”

Q What does it mean, sorry, to critically reason about your business? And if you were sitting in that founder's seat, what would you want to see? And what would impress you?

A When I say critically reason, I mean, oftentimes they have some direct or adjacent context where they can make some inferences about what's happening. For example, if you're running a marketplace business, They've worked in something that looks like a marketplace and they can say, Hey, I noticed that these three things are happening. And I think it's because you're having these network effects. And here's how I would like understand and measure it. And here's like, if this is true, we should double down, right? Like this is an early indicator of X. You know, they can make some kind of like really reasoned hypotheses because they've either seen it before or they understand the mechanics of business that looked like yours. Yeah. Obviously every business is very different. But, you know, these learnings do translate, and it compounds over time. And so the things that I learned at Instagram are very relevant still for, like, the work that I did for Stan and Jason and Discord, right? Like, even though it's a very different business, a lot of the insights, a lot of the questions they had, I actually had, like, a lot of very direct experience on four years ago. So what you're looking for is you're looking for some overlap in context that you think that they can get in the seat and actually start moving.

AI assessment note: “When I say critically reason, I mean, oftentimes they have some direct or adjacent context”

Q your North Star? Like you said there with Instagram, it's that kind of account of demographics and detailing. I think the trouble is a lot of founders don't know how to choose their North Star or choose the wrong North Star. How do you advise founders on how to choose the right North Star, and also how long to give it to know whether that's the right one to choose?

A Yeah, it's a great question. It's really quite hard, actually. Metrics are always a representation of your strategy, right? And so you shouldn't just choose a metric. You know, the thing that I talk to founders about is like, let's talk qualitatively about what is the magic of the product? What makes this product really tick? And how do we know that this thing makes sense? And what is our users telling us? And what do we see in the behavior of the product? And you can usually dial in kind of like your North Star metric by going through some qualitative exercises and saying, Hey, what is the magic of Instacart? What is the magic of Instagram? Like, when do you know that this thing is going to be really valuable to someone after they join, and that they've really found some long-term value? And if you can say that in words, then that really translates to a metric pretty easily. So for at Instagram, for example, you know, what we found was that people, after they join, after they see some amount of really interesting, visually distinct content in their feed from people they know, they want more. Right. And so like that qualitatively, that is a really easy thing to like be able to explain. So then what does it mean quantitatively? It means that like, well, you have to have a certain number of high quality connections who are posting pretty regularly for you to get that magic moment…

AI assessment note: “let's talk qualitatively about what is the magic of the product?”

Q be my advisor, and we're going to start this recruitment process. So I need a growth rep. Let's say it's the junior side, okay? Like we said, we're going to start with the junior. How should I structure the hiring process? What does first meeting look like? What does second meeting look like? If it was you running it, how would you structure this process to ensure the best candidates?

A Yeah, that's a great question. I actually fundamentally don't believe that the process is that different than hiring other execs or other leaders. I just think that for the most part, people feel that way because they don't really understand the concept of growth. So it feels like a little bit of a black box, you know, and it's also kind of hard because a lot of people will say, I'm a growth expert, but they're really only good at one thing. So you're like, well, who's really an expert? It's hard to calibrate. I'd say, you know, if the person is not working, which is a luxury or in between jobs, I find it better if you can do a consulting gig with a couple months, Have them come in house and basically give you basically an assessment of where they think, like how well your business is doing and what they would invest in. In a world in which they are working and you're doing a traditional interview loop, I would do kind of like first meeting is, you know, understanding what their background is, what their skill sets are, really walking through some of the things that they've learned and launched and how they kind of think about measurement and success. Honestly, like understanding like where they failed and what they've learned. What's really funny about growth is that like you have to be really humble about it because You don't know everything, and oftentimes you're proven wron…

AI assessment note: “I would do kind of like first meeting is, you know, understanding what their background is”

Q I mean this with total respect. When you look back at the different organizations you've been a part of, what made you join Pop Shop, having been in such different organizations? I'm just too intrigued about that one.

A You know, it was an interesting kind of path for me. I, you know, was thinking about what was next, and was doing a bunch of, I would say, passive recruiting, fielding some inbound, talking to recruiters, and I kind of realized a couple things. One was that, like, every job that I was Talking to was in some ways a turnaround, right? It was a turnaround because it was either there was an investment that needed to be made that hadn't been made, or you were replacing someone who couldn't scale, or they were like, you know, they were making a big pivot that they should have made like six months ago. So I realized that like, you know, every job, no matter what it was, like big fortune, 500 company, or like, you know, late stage private company required just like a lot of you to really help get the business going. And what I realized is like the thing that mattered the most is that you believe in the sector. You have an incredible relationship with the founder. That's gotta be something that you believe can be enduring because growth is hard and it doesn't work all the time and it takes a lot of cycles and a lot of trust to figure out the model. And so for me, you know, pop shop sat at the intersection of a lot of stuff that I had seen, right? Like when we were at Instagram, I was there when we launched IGTV and like, you know, heard Kevin Systrom's thinking around like the future of…

AI assessment note: “pop shop sat at the intersection of a lot of stuff that I had seen”

Q know, they have the data and they make bets, and bluntly growth go in, fuck up a load of code that the engineers have spent a load of time doing, and then try some bets, and then sod off. My question to you is, how do you think about that relationship between growth and engineering, how they can maintain a very productive and efficient relationship without antagonism between the two?

A Yeah, I mean, look, I come from a product-led growth background. Right. Where growth is a product function and it interfaces closely with marketing interfaces closely. And like, you know, when I helped build the growth team and Instagram, we were engineers, data science, product managers, growth marketers is like full stack, basically product group, but the engineers were growth focused engineers. There are different breed of engineers to be clear, right. That like get excited about doing different types of things than like an infra engineer or a traditional feature engineer. But you need to have a strong working relationship, and they need to be included in everything the same way you would with a traditional product or cross-functional team. And so it shouldn't, the growth team should not be a source of thrash. The growth team will be a source of thrash because the growth team's job is to always be pushing the envelope of what is possible. But it doesn't mean their process should be thrashy.

AI assessment note: “they need to be included in everything the same way you would”