The Exchanges

Q Yeah. So how did, how do you structure an org to build three and launch? I didn't realize they launched around the same time. It's like, I'm picturing, uh, Elon Musk launching three rockets at once. How do you, uh, how do you allow for that to happen?

A Yeah, I'm sure our product marketing team felt that way. Um, Yeah, a couple of things. We, we started really small with all of these initiatives. So, you know, I think I mentioned we, we really had one or two people working on, on each of these products for like the first six months. Um, so it was like one engineer and one designer or one engineer and one PM. And they really didn't get funding until it was clear that there was something there. So they just, those teams just, they spent a ton of time with customers, spent a ton of time building, a ton of time prototyping. And it was kind of the moment where I was like, okay, like there is a there there that, that we started bringing more people onto the team. So it was the first piece. The second piece is that we really treated them Like startups where like retools the VC and like retool funds with like resources and retools existing customer base, which is obviously quite valuable because you kind of have all these customers you can, can market to and promote to. But then the teams really had to prove out ROI either in engagement or eventually revenue in order to be able to move forward. And then the third thing, and this one actually I think It can be quite controversial is we were really deliberate about keeping these teams separate from the rest of the org, especially early on. And now a lot of them are, they're, they're ver…

AI assessment note: “we were really deliberate about keeping these teams separate from the rest of the org”

Q Hilarious. You talked about this idea of first principles. People talk about that often as we want to be first principle thinkers. We're going to think from first principles. How did Stripe actually operationalize that implement that? Was that just like founder top down continue questioning people and that trickles down? Or is there anything else they did to kind of instill that mentality?

A I definitely think it's founder top down. They were really good about hiring people who thought that way too. So it's just all that stuff. It just really, really trickles. And actually to this day, when I'm preparing like a memo or like a, a board deck or something, I imagine in my head, I'm like, what if I had to present this to Patrick? And like, my ideas just get so much better because it just like, sort of, I know like you can kind of think about sort of the questions they would ask. So I think that was one, you know, I think the other one was just a sort of this writing culture piece. Like people would just like, once you start writing things down, you realize like, hey, that actually doesn't make a lot of sense. And then I think the, the third thing actually was there was just always a lot of questioning about like the status quo. So if something had been done in an industry for a long time, people would always be like, well, why was it done that way? And I mean, I think this is kind of actually how Stripe got its start, right? Like I think when Stripe started, If you want to set up a merchant account, it could take weeks. And everyone just assumed, like, that's, that's what it took. And, you know, of course, John and Patrick were like, well, it doesn't actually make that much sense why it should take that long, so.

AI assessment note: “I definitely think it's founder top down. They were really good about hiring”

Q a very reasonable, conservative way to think about fundraising. And so I guess just thinking about innovation in general, why do you think some teams are able to run, like, like innovation machines continue to put out new products, disrupt industries, while other companies kind of plot along, stay conservative? Is there anything you've seen, something you bring to teams you work on to help foster innovation and big thinking?

A Yeah. I actually think about the, the extremes of that question. So, so not, you know, why are some teams innovative, but like, why isn't every team innovative? Like, I feel like no one wakes up in the morning and thinks like, yeah, today I want to work on like boring incremental stuff, but most teams do end up working on like pretty incremental stuff. I always wonder, like, what is it that's stopping folks from being creative and, and thinking bigger? And I think it comes down to like a couple of things that You know, companies do sort of unwillingly or not even sort of realizing it. And one is this fear of failure. Like, I think leaders want the upside of innovation, but they're not really willing to deal with the cost of innovation, which is like, look, if you're going to swing big, you will invariably stumble sometimes. So, you know, I think if you want to mitigate that, you have to start shining light on failure. That's, that's really the only way. Like, you have to start normalizing it a little bit and Obviously, like, if an individual or if a team is, like, consistently failing and not learning, that you need to, you know, you need to sort of deal with. But I think sometimes it's, it's good to fail. So, you know, like, and, and when, when you do feel it, like, use it as an opportunity. Like, don't squander that moment to, to not learn. But I think, like, one, one example…

AI assessment note: “And one is this fear of failure. Like, I think leaders want the upside”

Q I can't wait to see a picture of this. Final topic. You have this concept that you call the product talent portfolio. What does that mean? And how have you found that useful in your product leadership life?

A Yeah. Yeah. It's back to the, like all of product management is portfolios and funnels. I think it's really tempting as a manager to build a team in your image because you understand their skillsets and you value those skillsets and you're going to be able to detect and assess those skillsets better. But the best product teams in my mind have really figured out how to balance the, you know, the, the talent portfolio. So instead of sort of having a bunch of PMs who all spike in one particular area, figure out how you can, you know, have a, create complimentary skill sets For the whole PM team. So the whole is much stronger, and one way in which I like to do that is I really like to balance product teams with homegrown product managers who really get the product. They've, you know, probably been in it. They're amazing culture carriers often. They really set the tone, but they may not have seen product management at other companies, and they may not have some of the sort of more conventional traditional product management skill sets. So I want to balance that with product managers who've come From other companies and have done it and can bring a little bit more of that product manager rigor, even though they don't have that sort of, you know, the core and, you know, the retail case of the core retail product management, you know, vibe. So that's one example. I think there's like o…

AI assessment note: “instead of sort of having a bunch of PMs who all spike in one particular area”

Q And then on the second bullet point of urgency, creating, giving people a chance to think longer term, is there anything there that you found to be actually effective to create that culture and give PMs and product teams a chance to think longer term and not just be stuck in the fires that they're dealing with?

A There's a couple of top down things, and I think a couple of bottoms up things. On the top down, I think sometimes you just have to be willing to fund Some, someone with something. Like, they come to you with an idea, and you're like, look, yeah, like, take an engineer and, and go do it. And you just have to kind of give folks that, that sort of organizational buy-in. Like, actually, I was thinking back to that, that engineer, Brian Krause at Stripe, who started, you know, kind of poking around on these, on this marketplaces model. And I was thinking, like, I can't remember a moment when someone formally said to him, this is now your job. Like, I think he just kind of went and looked. And, and went and, and dug into them. At some point I think a manager was like, all right, this is now your job. But yeah, I, I think you have to be able to sort of like fund, fund folks' time and, and give them that. Hackathons I think are like pretty good for that stuff. It is kind of a moment for folks to, to take a step back. And then, you know, I think more than anything in people's planning processes, like I really like asking folks, you know, like the sort of the 20% more time question, or the other question is like, look, like if you doubled the team today, what would you do? That shows up in our planning processes as well. And I think it really helps people kind of break out of this. Like…

AI assessment note: “On the top down, I think sometimes you just have to be willing to fund”

Q of product at Retool, but before that you spend a lot of time at Stripe. You spent six years at Stripe. And so before we get to Retool, I actually want to spend a little time on Stripe. To set a little foundation, could you just talk about some of the things you worked on at Stripe and maybe some of the things you're most proud of during that time?

A Yeah. So when I joined Stripe, I joined Stripe in 2013. It's pretty small at the time, around 50 people. And Stripe didn't have any product managers at that time. And I think Stripe was kind of famous for that. And it really wasn't because, you know, we were anti-PM in any way. It was mostly just because we were building this product for developers. We had a lot of really talented engineers who were essentially doing the PM job. So I actually joined Stripe as the first account executive, which I think it's pretty funny now that I've seen, you know, real account executives do their jobs, because I, I really just had no business doing that job, but it also really wasn't your typical sales job, and that most of Stripe's volume was inbound, so I was really just spending all of my day talking to customers, helping them figure out how Stripe might work for their particular business flows and, and payments models, and a lot of it was, I think, you know, what PMs do, it's just like talking to customers, understanding their pain points, and, and really helping them figure out how the product might do that, so. And to this day, when people ask me, hey, like, what's your advice for going into product management? I'm like, well, you should go get a sales job. I think it's like pretty, pretty valuable. But it's kind of a long story, uh, to explain that at the time there were, uh, there was …

AI assessment note: “I actually joined Stripe as the first account executive”