TECH TITANS: Mastering Hybrid Culture with David Singleton, CTO at Stripe

(Intro Narrator at 00:00:01) Today, we're bringing you an episode of Tech Titans. David Singleton, CTO of Stripe, joins us in this episode to share his best advice on how he cultivated a strong hybrid work culture. You're listening to Joel Beasley, Tech Titans.

(Joel Beasley at 00:00:20) Do you have any ideas, and this is pretty far out there, so how do we get—I get to talk to great leaders like you, right? And we talk about these operating principles, and then how do we get those to elementary or middle school kids? How do we get those concepts earlier into our culture and society?

(David Singleton at 00:00:45) So it's a really great question. It's actually, I mean, it's been very fun for me seeing my daughter. So she's in kindergarten and about to go into first grade at school, and seeing, certainly, the experience of school—she goes to school in San Francisco—but the experience of school that she's having compared to what I had as a kid is very different. There is a huge amount of affirmations of the kids that they can learn.

(David Singleton at 00:01:14) At this, that growth mindset thing I mentioned, that's something I've thought about for years. I was actually pretty blown away that in the first couple of weeks of school, my daughter came home and told me what the growth mindset was. Maybe her school is unique in that regard, but that's something I think all school kids should know. And can I call her school? She is not. She's at a private school. But the public school on my block, where we have neighbors, friends, and I've gone in and helped with a few of their events, do exactly the same thing, same materials that my daughter's school uses. So that's awesome. I do think it is a very important thing to emphasize when folks are setting on the learning journey that everyone has.

(Joel Beasley at 00:02:03) I love it because, you know, I'm not there yet. I just have what happened to me thirty-two years ago, and that seems pretty—there just wasn't any conversation about it. I mean, it was just here's the basics that we know in math, here's the basics that we know in science. Good luck, right?

(David Singleton at 00:02:22) Right, and the art teacher who said, "Oh, that picture is terrible, so you're never gonna be an artist."

(Joel Beasley at 00:02:29) I left art and then went into the drama club thing because it was more interesting, to be honest with you. I had to do a monologue. I was really, really shy, and so I figured, okay, if I go over there and they force me to do a monologue or something, that would help me on my growth.

(David Singleton at 00:02:54) And it did, that's cool. I guess I actually had a very similar experience. I had a particular teacher, one of my languages teachers, and she noticed, I guess, that I was a bit shy about, mostly about speaking in a foreign language, to be clear. I don't know that I was particularly shy in English, but she made me go to the speech and drama club. "Made" is maybe a strong word, but strongly encouraged. And that actually has been a very formative experience for me because the ability to speak with very little preparation was something we practiced there. The ability to act and kind of have a bit of confidence in yourself I have found quite important in both, as a manager, how I work with people in a one-on-one setting, but also being confident enough to get out and talk to a big team and answer questions that might be pretty tough questions off the cuff. And again, just like we were talking about with art or science or math, whatever, it is something where practice really helps. And it certainly has helped me do what I do today.

(Joel Beasley at 00:04:03) Yeah. I noticed when I did 50 talks last year in person, and then since the COVID stuff, I haven't been doing talks, and I remember, you know, looking three years back, I had done virtually no talks in person, like one or two. And looking at, once you get into that routine of going on the stage and going to the different city and then speaking, you get so incredibly comfortable with getting to talk to complete large audiences of strangers. And I think the thing that's helped me most or the thing that built my confidence from being so shy and quiet is I put myself through, or I found myself in difficult situations in life, and those were opportunities to get to know who I am. And so I just became really confident in who I am as an individual and knowing myself and knowing that sometimes I'm up and sometimes I'm down, or sometimes I go through these patterns where I'm more interested in these certain topics. And, you know, there were times getting to know myself where I tried to fight that, be like, "No, I'm just gonna be this one thing. I'm just gonna go a mile deep." And then there were times where I realized, you know, there's this balance that I have to achieve within myself. And so when I step back and look at life from this continuous journey of getting to know myself and understand myself, that allows me to interact with other people in a more fluid sense.

(David Singleton at 00:05:25) Yeah. That's really awesome. People often ask me what my management style is, and when I was probably first asked this, fifteen years ago, I tried to answer the question literally. I was like, "Well, I do this and this and this." And that's not untrue, but if people ask me that today, the answer I give is adaptive. I know that doesn't sound very interesting, but it's true. I really, over time, just as you described, spent time introspecting on what is the right way to engage and mirror my own energy and my own passions in all the different ways. So yeah, great observation.

(Joel Beasley at 00:06:02) Has introspection provided you a lot of benefit in your experience?

(David Singleton at 00:06:07) It certainly has, and it was not something that came naturally. I think, so I grew up in Ireland. It wasn't a particularly introspective culture. I did a lot of the stuff we were talking about, you know, speech and drama stuff, which never really invites you to look into yourself. It's more kind of looking outwards. But through the first maybe five years of being a manager in particular, I realized I'm encouraging folks that I work with to introspect. I should do more of that myself, and it's been very valuable.

(Joel Beasley at 00:06:39) Yeah. You know, I find that too. I find that sometimes I'll hear myself talking and I'm saying, am I talking to this person or am I talking to myself? Because the advice that's applicable to them is the same thing that maybe I should be working on. It's not all the time, but sometimes, that sleepy process that's in the back of your mind that's running autonomously will kick up and say, "Hey, this is a hook. This is one of those moments where you need to actually implement that advice in your own life."

(David Singleton at 00:07:04) Right. Well, right now, I get asked a lot—so you mentioned you haven't done a lot of talks since COVID and our regular schedule has kind of changed up from that as well—but I spent quite a lot of time talking with other CTOs recently, and I guess we've spent a lot of time talking about how all of our various different companies are responding to COVID. And at Stripe, you know, all the stuff that I just talked about, really paying attention to how we're working, has really worked very strongly for us. So we have been, we invested last year a tremendous amount in setting up a remote hub. So we had been building offices as hubs for Stripe product development around the world for, I don't know, six to nine months before that. So today, our engineering offices, if we're not all working from home environment, are in San Francisco, Seattle, Dublin, Singapore as hubs around the world. Then we've got some smaller offices across the US and internationally.

(David Singleton at 00:08:13) Remote engineering has been a big part of the culture at Stripe since the early days. And I think we first came to that because there were just people that were particularly talented that we wanted to bring to Stripe, and they were not in the Bay Area. And so some very early engineers at Stripe were remote. And we did a lot in the culture to make that work well. So for instance, the document-based culture I talked about earlier, to some extent, came about to help folks who are not physically in the room be able to follow along and be part of a discussion. So also, when Stripes have a discussion maybe in the corridor or in a one-on-one setting, we'll tend to exercise what we call email transparency. So we'll actually send a note about that to the team mailing list so that folks who are not physically co-present can follow along. So there was a lot in our culture already.

(David Singleton at 00:08:45) Exactly a year ago, so it's May last year, we decided to start treating our remote population just like we do a hub office that we're trying to stand up. Because there was a lot of work that we did to get those off the ground. So in particular, we would appoint a site lead. We would make sure that folks in the leadership team were traveling there a lot to help, you know, share information and make sure that there was good connectivity with the team and the rest of the company. We would also do events with the local community, which obviously was both to let folks know Stripe is here and we can help you use Stripe, but also for hiring purposes as well. And in retrospect, it seems kind of obvious, but it didn't occur to us, to me, until a year ago that we should think of remote just as another hub. And so we did that a year ago, and we appointed a site lead, and we've been really leaning into making remote even more successful.

(David Singleton at 00:10:01) And it's been, I think, very successful for us. So over the past year, we have three times as many remote Stripes as we had a year ago. It's now 22% of our engineers are remote, which means that other than San Francisco, it is our biggest office if you think of it that way. And those same things I talked about turned out to be super valuable for this population of Stripes. Having a site lead who can actually go talk to people and understand what's working well and what's not working so well, connect the patterns, see the themes, build the systems that help, has been tremendously valuable.

(David Singleton at 00:10:30) And some things that have come out of that include, we now have really good guidelines for what AV equipment you should use. We have a bunch of norms now around team Slack channels. So most team Slack channels might have a social channel alongside the main work channel where folks can connect as human beings and stay in touch with how each other are doing. We also have, we've kind of learned from our remotes that not every meeting needs to be a meeting. You know, you can work in a document at the same time and make a tremendous amount of progress when you're collaborating and you're maybe talking in a Slack channel, actually working on a document together.

(David Singleton at 00:11:18) So that's been really valuable for us in really making remote work great at Stripe. It's been extremely valuable for us as we pivoted the whole company for working from home in the current COVID environment. So really a tremendous number of the tools and systems that we had set up because of having the remote hub have been extremely valuable there. And this culture of talking to people and seeing what's working well and not working so well has been pretty remarkable.

(David Singleton at 00:12:05) So we've been doing weekly pulse surveys since everyone went remote at Stripe. And the data that we hear back from folks is actually quite different to what I might have expected before we kicked this all off. So we survey on things like, how would you rate your connectedness to your team, and how would you rate your productivity in your current environment. And right away, so early March when we all went to working from home, the initial results were quite surprising. So the initial results for connectedness to the team were actually, the majority of people felt either as connected as they did before, or more connected.

(David Singleton at 00:12:47) And that has just been monotonically improving over time. So now a significant majority of folks at Stripe feel more connected to their teams in this environment where folks are working from home than they did before. I think that's pretty remarkable, and it's not what I expected. But there's also a sizable group of folks that we work hard to really enable and support, and we listen very carefully to their feedback, that feel less connected. And there's a lot of work to do still to have the right setup to make this work better.

(David Singleton at 00:13:19) When it comes to productivity, again, right on the very first week that we were doing this—and, frankly, I think a year ago, this would have been extremely challenging for Stripe—but because we had gone through the process of really standing up a first-class citizen remote hub and then taking those patterns and applying it to the rest of the org, we found that right out of the gate, the majority of people were either more or at the same level of productivity, self-reported, as before. And again, we've seen that monotonically increase over time. So it's been a great experience over the past year in enabling our remotes and growing our remote population, and then it has stood us in remarkably good stead for what's going on right now.

(Joel Beasley at 00:14:03) For this remote hub thing, did you talk with other CTOs, or are other CTOs doing that? Have you shared this with them?

(David Singleton at 00:14:11) Yeah. So again, we really believe in learning from others' experience. So before we do anything major like this at Stripe, we'll tend to go out and try to talk to as many other companies as we possibly can who may have seen similar things to us before and try to learn from their experience. Before we did this, as I mentioned, we did already have a relatively large number of remote Stripes. So it wasn't the case that we were making a decision of are we gonna do this at all or not, but we did want to figure out what we could do to make it as effective as possible.

(David Singleton at 00:14:45) So we talked to people who were at fully remote companies, companies like Automattic who build WordPress, GitLab, which is fully remote, and also some earlier-stage companies like Coda that's fully remote.

(Joel Beasley at 00:14:59) Oh, I know Coda. Are you kidding? What? You just tickled my brain in the best way. I'm sorry to interrupt. I was like, Coda? I used to love them.

(David Singleton at 00:15:07) Yeah. Well, they are a fully remote company, and they actually, I think it's pretty valuable for their product because their product is all about how people collaborate in those ways. So the point is, there are a lot of folks who thought hard about this, and we tried to both learn from their experience and figure out what would transfer well to Stripe. We also talked to companies that were not doing this to understand why were they not doing it and make sure that we didn't feel like we're gonna hit any rocks in the road. But we ultimately, of course, decided that we were gonna do this.

(David Singleton at 00:15:24) I think some of the most important lessons that we've learned are, and I think this could be of particular interest to folks thinking about what they're gonna do as COVID restrictions start to relax, we were in a mixed model, right? So a lot of CTOs I talked to would say, "Hey, it's great if the whole company's remote, and it's great if the whole company is kind of office-centric, but in between is harder." And it is for sure. But we are obviously working hard to make that work. One of the things that we've noticed is it really is the case that one is the loneliest number. So if you're a single remote engineer or designer or whatever your job is, working with a team that is primarily based in offices—they may not even all be at the same office, but in offices—then the burden tends to fall on that person to be the kind of momentum to shift the way the team works, even with a tremendous amount of organizational support.

(David Singleton at 00:16:33) So we just don't do that. We make sure that teams that have remote members are at least half remote, as much as we possibly can. And we've also stood up a large number, in fact, of entirely remote teams, so that the way that they work is kind of tuned to the way everyone will most benefit from. We've also really found that investing in tools and communication norms is important. So, I mean, one example of tools. One of the things that I heard from someone in another company was, we were really, really worried about having lots of remotes because we still depend on all getting together in a room when there's a crisis.

(David Singleton at 00:17:21) So instant response. And we were still doing some of that at Stripe before we started our remote hub. But we really put a lot of investment into tooling for incident management. So today, if something happens that we need to respond to as an emergency, people at Stripe can press one button, and it stands up a virtual war room. So a set of Slack channels with tools to help with collaboration.

(David Singleton at 00:17:48) And, I mean, I don't really know what the counterfactual is. Maybe we would have built that anyway, but we definitely built it because of hearing some of these insights. And we use it as our primary mechanism for doing these things because of hearing some of those insights. And that's been valuable. And communication norms, I mentioned already, like, having a doc that you're collaborating in. One of the things that has been, I think, pretty valuable comes from treating the remote population as a hub is having leadership Q&As with the team, where we're just trying to create really transparent two-way communication.

(David Singleton at 00:18:26) That is something that we started doing over Zoom. So if I would visit an office, I would leave my home office, typically, like, you know, get everyone together in a room and, you know, have a little bit of spiel of what's going on right now, but then, you know, answer questions. It turns out you can do that just as effectively over Zoom. You can have a 100-person Zoom meeting. You can shepherd questions in a Slack channel so that everyone's not interrupting each other and kind of agree who's gonna go next to ask their question and have a really high-bandwidth, large conversation.

(David Singleton at 00:18:59) And so we started doing some of those things for our remotes. And now that the whole company is working remote, we started doing that at a company-wide level. So our company Q&A, which Patrick, our co-founder, runs each week, is now really kind of a big rallying point and sort of focal point of the week. I love it. It's probably my favorite meeting of the week.

(David Singleton at 00:19:22) And again, we kind of learned some of those techniques through making the remote grid super effective.