Claire Hughes Johnson on being a “learning organism” during Stripe’s growth, and more scaling advice for leaders

 Thank you, Brett. great to be with first round.

 so I thought one interesting place to start is, you know, every startup when they get into this growth phase begins to, to build their executive bench.

 And in, in our experience in working with a lot of companies, this process often leads to sort of this rotating cast of characters where execs come and go, a CEO's incredibly excited about, exec X, and nine months later, they're no longer at the company.

Um, and I'm curious, when you reflect on this transition, you know, you, you, you had this big chapter of your career at Google and then went to Stripe. There's so many amazing people that were at Google and then take a big exec job, and it blows up in nine months, as I was saying. And so I, I'm curious, w what do you think when you reflect on your own, either ways that you behave or what's kind of going on for you that you were able to stick and have this many, many year career at Stripe?

 A a lot of people have tried to ask me that question, but not so artfully Brett. Um, well, I appreciate the underlying thing, which is, yeah, it didn't blow up. Um, and I'm still involved with Stripe, but I don't know if I will ever not be, because I, I feel so tied to, 

To the company and the founders and everyone there and what we've built. I'll give you my assessment. I think there was an amalgamation, as you suggest, of some things that had to do with my sort of d n A and makeup. Some things that had to do with, uh, the hiring process, honestly, and how much time I spent with, uh, the founders of Stripe.

And then I think the third part is probably actually cultural, a little bit in Stripe. so yeah, in part one, I was, you know, pretty early. First of all, I, I, my career is not a very. Straight line. And I took a lot of different kinds of risks. I graduated from college without a job and started working on political campaigns.

Uh, I kept getting into law school and then saying no, and realizing I should try to go to business school, which based on my upbringing was like a very radical thing to do. Obviously not radical when you say it out loud, but, uh, but my parents were appalled. Anyway, uh, I go to business school, I end up, uh, working for like a startup consulting firm that was pretty scrappy and also had technical, had engineers, right?

So I started getting into technology. Um, but point is I think I'm pretty entrepreneurial. I think I'm a more of a risk taker, uh, than your average quote unquote executive. I've never been comfortable, even still today, once people call me an executive, I, I kind of start laughing. Uh, so I think that that spirit in me, I mean, it was just crazy to me when Google, Google was the biggest place I'd ever worked and I joined, it was about 1800 people.

Um, and then when I left, it was almost 60,000 people. And I was just flabbergasted that I worked at a company that was that big because it just wasn't my jam. Um, so I think I'm pretty entrepreneurial. I'm not afraid of risk. I saw the opportunity for Stripe, even though it was so early on, it was like 160 when I first started talking about Patrick.

It was like 80 people, barely. Um, so that's part one. Part two is, yeah, the hiring process. I mean, we just, the collisons, I mean, if you were gonna fault our hiring of leaders is that we always took way too long, uh, because there was a little bit of looking for that perfect candidate. And then you realize, of course there's no one perfect.

And I wasn't either. But we certainly, there's a lot of diligence done on both sides. Uh, a lot of conversations. We even sort of practiced working together. Like I drive to SF from Menlo Park and hang out in the office with them for a couple hours, a few nights, and we like wrote company goals together. So I think the hiring process was very thoughtful, lots of mutual diligence.

There were no surprises really. When I joined, um, I'd seen a lot of the data and written, again, I helped write the company goals before I joined. Um, so that, uh, was pretty critical. And I think, um, and I think the third part is, We really worked hard as a leadership team to be introspective about giving each other feedback, but also shifting our portfolios, thinking differently each year about what people's value would be and where they could have an impact, which was good for my development and my growth, but also I, I'd like to think I helped create some of that open environment and that willingness, at least I think early on, we didn't hire anyone whose ego got in the way of the right thing for the company. Um, and if we did hire that kind of person, we would part ways with them. And I really thrive in that kind of environment. And I think, so my cultural alignment, but also the fact that the culture, uh, kept, you know, the spirit that the founders had, we were just like all really in it for the long term. Uh, and that, that meant a lot.

I think there are some people who get a certain type of career success and they th they think like, well it means, you know, big money, big title, big company. Right? And, and to me, career success is big impact and I don't really care what seat I'm in.

 There's a lot to kind of dive in on there. I, I'd be interested to, to hear at, in a more granular way what that hiring process looked like and when you were kind of getting together, even if it was more about time and less about structure, what was going on in that time, uh, when you were together, what are the types of things that you explored together?

 Yeah. Um, as I say, you know, in the book, in Scaling people, I have, I have a little section on, um, me joining as coo cuz there's a lot of questions about that role and should you hire one and, and I'll give you what I think the context was at Stripe at the time because I think it, it is relevant to what you're, you're asking, which is the company had started to really, obviously had product market fit, was getting real traction.

Um, and my sense was that the investors were rightly and the one board, the one board member who is Mike Moritz from Sequoia, um, were starting to, to give a lot of strong, strongly worded advice to the founders. Like, you gotta grow a little faster, like you gotta invest. Um, strip's always been quite conservative, at least ally early on in, in sort of the p and l, but also just in adding people.

Um, and, and I think there was a real need acutely to really build out sort of sales in particular. And so Patrick and John Patrick in particular was on a journey, from what I could tell, meeting sales candidates and or COO candidates. And I will share a lesser known fact, which is Stripe had a coo. O uh, so Stripe, my colleague, who by the way was, has been at Stripe longer than I have, uh, is a guy named Billy Alvarado who was hired.

He's like a bd Jedi. I mean, the guy is a master and very strategic and also very smart about payments. And he, um, and, and in another story about doing work before you're hired, so I helped write the company goals. Billy helped do a deal with Wells Fargo before he was hired, which I love. Uh, he, and somehow the Collisons have that effect on people.

You just start working for them before you're working for them. Um, but anyway, Billy was the coo and Billy was, this is what I mean, I guess, about the culture, which is Billy was really aware that there were aspects of what the COO role needed to be for Stripe as it hit the scale moment that were not his favorite.

Like not, not only did he not love them, he, he, you know, often the things we aren't as passionate about, we're not as strong at. And um, he. Was part of my interview process, right? Like, that's a big deal. Like, he was like, look, I want you to take my job. Um, and, you know, he became the chief business officer. He, again, critical colleague, critical builder of Stripe, really needed to focus on our payments and our product partnerships on some of our sort of international payment infrastructure work.

Um, but point is he actively recruited me to be the coo o and then when I joined, there was this awkward thing where Patrick's like, well, we don't really feel like we should give you the COO title when you first start. This is after I'd been recruited for like six months as the coo, and I said, Uhhuh, and I'm, for a minute, I'm, I'm thinking, wow, I really trusted these guys.

Is this a bait and switch? But they, I think Patrick had a, a legit concern, which is the company didn't know how long I'd been talking to them and how we'd all gotten to know each other. And obviously Billy was an important figure. And they're like, Patrick's like, I think people might think you're taking his job.

You know, and that it, it reflects on him. And, and so we came up with chief of Business Operations. That was my initial title.

 Very fancy and very kind of amorphous, which type likes either no titles or something really amorphous. So, um, and then we, like a few months in, actually not long, Patrick just sent a short note out to the company.

He's like, Claire is no coo and Billy is now, you know, chief business officer. Goodbye. You know, like whatever. No big deal. Um, but I think that the interview process really, we spent a ton of time on the sales stuff, actually building sales, what would go to market build look like. Also internationalization, which was really happening at the same time.

And they're related of course, cuz you need to build, go to market in all those countries. And I think this is part of, they were talking to a lot of sales leaders and then talking to me and of course I've built sales teams and I've been a sales leader, but I actually didn't want a job as a head of sales.

And I was very clear about that. I was like, I know that I can do it and I will help build sales for Stripe, but I'm not gonna be the ultimate like revenue officer. Um, just because it's not everything that I care about. And, you know, I'm, I'm more operationally wide, I guess was what I was trying to say.

And they had a decision to make, which is, well do we go for, do we give this. You know, ostensibly bigger title COO to, uh, to this person and trust that they will be able to put the scaffolding and start to build this critical function. Again, at the time was sales. They were really fixated on, um, and then eventually that she or we will hire, you know, who is needed to help lead that function.

And, and I think what happened also, so one is I think they became convinced that I knew enough that I could in fact build it and I haven't built it before. Um, but then they also got some bonus topics essentially, which is one I had a lot of support and operations experience. And our support situation was a little bit of a tire fire at the time.

Uh, and I had some real opinions about what we'd have to do there. And then the third was that I cared so much about company building. you know, I care about the people side, the org side, the, the structures you needed to put in place to have a healthier company. And to their credit, they came back to me and they're like, you know, you kind of talk about some of this stuff on the company side and we just don't talk about it.

We don't, we haven't been thinking about that and we realized we have a blind spot and you care and you could fill it. Um, and that meant a lot to me cuz it meant they were really listening. They were paying attention to what I cared about. And they were looking for a way to put a portfolio together of what they needed, but what I cared about.

But also admitting that maybe the company needed some things they didn't know. Um, which shows that they're learners, right? They're curious, um, they're interested in, in changing how they think about the world. And so in the end, the portfolio I walked in with was sort of a combination of those things. Um, and as I said, and it evolved over the years.

Uh, I added, you know, marketing, I added at one point risk, um, our workplace and real estate stuff. But I also gave stuff up. You know, we, we've moved things around. Um, but it, it, it was that iterative process of what does the company need? What is my career aspiration and skillset? And then what might I bring that, that they didn't even know the company needed, and could I take responsibility for that?

So Billy ended up handing over some things to me, um, that were all in his, he was holding them as well, um, that we weren't sure would be in the COO remit, but it started to make more sense as we got to know each other.

 What did you learn from Patrick about wooing exceptional talent that maybe is differential than, you know, you, you already had a big career coming in and you've recruited in that role. Lots of exceptional people. Were there net new insights in studying what he does That is part of your sort of, um, repertoire now.

 Yeah, I, I mean that is a fantastic thing to try to package up. I mean I think the number one thing is I think he will relentlessly pursue until he can get the conversation with the person that he is heard great things about he'll relentlessly research, right?

Who are the best people? Um, in fact, I was talking to an engineering leader who worked for me at Google a month ago who I met up with cuz he was in Boston and he was describing Patrick's reference call for our current C t o David Singleton, who we both worked with at Google. David. Um, I was part of the reason David came into the Stripe orbit, but Patrick certainly really hired him and closed the deal and Patrick did a reference call with Richard and Richard said to me, this is, by the way, this reference call was years ago now.

And Richard was like, this reference call feels like it was yesterday. He is like, look, it was the hardest reference call I've ever experienced in my life. I was, felt so much pressure, not just cuz it was Patrick Coll and, and because I care about David and the right thing happening. He's like, but because it was like intense and he said that, um, Patrick at the end asked him, you know, a lot of very detailed questions about how David works, but then at the end said, who have you worked with?

And this is mostly at Google, right? Richard had been at Google for a while at Google, who David is better than, and who is better than David. Um, you know, engineering leader wise, right? But if you think about that as a research project, if you do enough of those calls, you're gonna be mapping a certain type of talent, uh, in a pretty interesting way, right?

Which is you're, you're interviewing these folks about other people, and then you're asking them who do you know? Um, and then these people are are, you know, one would think pretty talented themselves if they're being offered as references for executives, right? So there's this very interesting, but anyway, Patrick does the research.

He's relentless in the pursuit of getting the meeting with the person. He's incredibly persuasive in the initial meeting. Not in a take, take this job, you know, but in sort of, you know, his own manner. I mean, he's just a very, um, incredibly intelligent, but also curious and worldly. And, and he has a lot of ideas and he has a really nice mix of his own opinions and things he's curious and interested in that are not just Stripe, but also about any individual he meets.

You can just feel like he's just collecting knowledge. And I feel like, great, but you know, we have, you have these. Dynamic conversations and you learn about what he sees for Stripe, which is inevitably bigger than what you thought it could be. Um, and then I remember distinctly, like after one of our, our first conversations, he was talking, um, about Stewart Brand and the whole Earth Catalog and then computer lib this, this old sort of newsletter that was created that was really formative to his interest in technology.

And next thing I knew in my office at Google, a package shows up where he has tracked down cuz computer lib is like not published anymore. He's tracked down and paid for a vintage old book copy of this newsletter and sent it to me with, you know, a note about what he thought I might, I might enjoy in. Um, after our conversation and you know, that's like an old tactic in the world, but it felt very genuine. It felt really authentic and it really related to our conversation and to his ability to share his knowledge and his passion and then connect it with someone else's. So part of that is just being himself, honestly.

And so you have to figure out how do I beat myself in a way that is really persuasive to someone? Um, and, and I think I couldn't say no to another conversation because I just like loved talking to him and I didn't feel like he was pushing the hard sell. He was, he was doing his own investigations.

That's the other thing is he's not, You know, blindly selling, he's really trying to make a match. Um, so I think those tactics and then being diligent throughout the whole thing, really, you know, probably too many interviews. Um, you know, I famously ended up interviewing with everyone at the company in one, you know, massive all hands meeting where I had to answer questions.

Um, and then also the diligence on the references. Uh, there was a point where I had mentioned offhand to Patrick and John that I'd send video messages to my global team because I was just sensing that my email updates, cuz you know, you have a global team, they're in all time zones, you can't get them all together at once.

So I do these email updates and they were getting kind of long and I was sure the open rate was crap and that no one was really reading them. And I was like, well, why don't I, I know this seems very trite right now, but this was actually somewhat innovative at the time. Like, why don't I just send a quick video message, which is much more efficient, they can watch it in their own time.

And like literally I would be with like an iPhone in my office on a like, you know, tripod recording these three minute messages, uh, to email out. And I offhand mentioned that to Patrick and John and they were like, can you send us something? and can you send us an email update that you sent to your team?

And I think like, I don't know if it was just that they wanted to see what I was like as a leader or they didn't trust that I did this, or they wanted to see, I think it was both by the way. Um, and so yeah, I ended up, uh, I had to actually edit, I had to edit out some Google specific content. Don't worry, Google, I protected you. Um, but I, uh, you know, I had to x out the numbers for the quarterly goals cuz that was a sales team. But anyway, point is, I did send a couple examples to them, but they were relentless. They were like, if I didn't send them, they'd say, well, can you send those things? Like, they were not gonna hire me without seeing examples of my work.

Uh, so that was, and we did that. We, there's a form of, that we've done with a lot of candidates to strive is we would like look for either a work sample or do a workshop with a candidate. Like, let's just take a real topic and sit in a room with you and give you some pre-reads and have you talk to us.

It's very effective. Um, you really do get a sense for not just the interview person, but the worker person.

 Yeah, you're touching on this a little bit, but sort of given what you shared h how did it map to some of the changes you made when it came to recruiting exceptional talent and, and you sort of mentioned this point about authenticity, which I think is really important. You often, I think one of the weird things is you see there are certain people who are around incredibly charismatic people and then they try to behave in that way.

 really, you know, somebody trying to be charismatic is probably from a hierarchy perspective, one of the worst things you can do. And so I'm curious maybe how did you adapt some of those insights that you picked up into what it looked like when you were going after talent?

 Yeah. Yeah. I, I would say, I think definitely being more patient and being more willing to pursue and being more willing to, I'm not someone who asks for help very easily, but I really, you need to use your network. You need to ask for introductions. So I learned that I, and in terms of the authentically showing up, I think that has always been a strength of mine, if I'm gonna be honest.

But what I will say is I learned pretty quickly, uh, Brett, that I needed to pitch Stripe in my own way, right? like if you put me in front of a candidate and I was parroting out Patrick's vision or John's vision, it was not as effective. And I, you know, there's one version of the story where you think, well, I've gotta say what the founders would say.

No, actually, it's not authentic to me. I had a reason I joined Stripe. I had a vision for Stripe, and that was much more compelling to candidates. I have this like whiteboard drawing that I would draw for what I thought was possible for Stripe. And I tried to draw it for Patrick and John once, and they were kind of like, yeah, okay.

You know, I mean, it wasn't the, just the way they tell the story. but I had to get comfortable that it's, it, that's my version of the story. And, and none of us are wrong, by the way. We hadn't built the thing yet. Um, and it was working. Like, I, I think that version of authentically talking about what the company could be, um, true to my own version of it was, was really important.

Um, I'd say that. And then I think just never stop the diligence, do the reference calls. I will say though, I don't think my leader hiring track record is as strong as my other hiring track record, and I don't know why that is. I think that I can, I'm very care, I care a lot about collaboration and if I'm hiring an executive, I think I'm thinking of them like, you're my team.

You know, you're kind of like my teammate and we're gonna work together. And I, I maybe didn't push hard enough on some of those and that, and Patrick would've, Patrick would've pushed harder.

 What else? When you. That sort of self-reflection comes to mind for you And and when you say hiring for other, you mean non-executives or something else? Specifically

 managers. Anyone else? Like I'm, I have a high hiring bar. I think I have a pretty good eye for talent. I will tell you that if I've worked with someone ever in my career, I have a very good eye for talent. Um, you know, it's a little different when you're in an interview process. But for example, we have this stripe, you know, in our applicant tracking system.

You can sort of say strong. Yes. And I have rarely ever used the strong. Yes. But when I used it on any candidate, let's say there were 10 maybe, so I'm not talking about a lot. They all ended up being top performers like I knew immediately. Right? But if you gave me an executive, I don't, I don't for some reason have that same insight.

Um, here's my theory. My theory is that in the same way that early in my management career, I had a thing about sort of wanting to be liked by my team and I was too nice, let's be honest, and not setting a high enough standard, uh, which I got over. And actually being at Stripe, I really got over it. I think I got a good balance between, I think I'm a very empathetic leader.

Um, but I have, I think my teams felt I had really high expectations of them, and I would give them the feedback if they weren't being met, right? I, I wanted results. Um, and I would think, I think in some of my errors at Google, that was not as true. Um, I certainly did well, but. You know, Google was on its own momentum.

Um, the point is, I think what happens to me in some of the executive hiring, or certainly earlier on at Stripe where I was, you know, at Google, I wasn't really hiring executives. Maybe at the very end I was actually, but, um, at Stripe, it was a new skill for me. It's a little bit of a different motion as, as they say, in sales.

Um, and I was trying to be liked, I was trying to recruit the whole time, right? I wasn't, I wasn't pushing hard enough on really getting underneath how they would work and how, and frankly, the other thing I wasn't pushing hard enough is I was making the assumption, okay, if you got to be this successful in your career, you're gonna adapt and be successful in our environment.

And guess what? As you said, Brett, a lot of those things blow up. You know, I adapted and was very successful in Stripes environment, but I am, apparently, I'm not the norm necessarily. Right? And I was doing that thing. This is another management lesson that I would share, which is you have to manage different people differently.

And too many managers have grown up being told the golden rule, right? Treat others as you want to be treated. in fact, the golden rule is not a great rule for management. You need to study those people and figure out what gets the best out of them and what gets the best out of them is not what gets the best out of you usually, especially if you've hired a diverse team, which I hope you have.

And so I think on executive hiring, I was making assumptions about my executive skills, um, and my personal skills and grafting them onto people who had, you know, great track records and saying, well, they'll, they'll have those same skills, you know, they can handle this environment, they can adapt. And that was wrong.

That was wrong. Some people, uh, no, the answer was no. Um, just flat out just being successful. You know, I think one of the, the most telling things, by the way, as a side note, but because we're on this topic, um, as you said, you can have this leader that you hired that you're really excited about, and then they flame out in, you know, six to nine months.

The biggest indicator that I could find in our time at Stripe when we had that issue was, uh, people who joined as leaders, as a, you know, executives and didn't hire anyone good in their first three to six months, that's an indicator that there's a problem.

 assume when you think about your directs, or even given the scale that you are operating, the directs of the directs, I would assume, and correct me if I'm wrong, an enormous percentage of their job is who's on the team, who's off the team, and how they're managing it.

So obviously you're sitting down and you're thinking very critically about this person's ability to evaluate and recruit talent ahead of the process. And so you're hiring them with some level of conviction they can do it, and then it doesn't happen. So what's going on there?

 And actually Brett, one of my favorite executive interview questions, I now have like convinced people, I'm not credible on executive interviewing, but let's say I'm not that bad at it.

 but anyway, one of my favorite executive interview questions is tell me about your current team and why you chose the structure that you have everyone in, and then each team member, how they got in that role.

Right? You learn a lot. You learn, and because what happens is they say, well, I came into the job and here's what I had, and then here's the choices I made. And there was this person and I elevated them, and there was this person and I, you know, maybe fired them. And there was this like, and it's a real red flag if someone's like, well, this is the team I got, right?

Like, I would never hire someone, especially in a scale environment, like who said, I just took what I got, you know? Um, and also that means they're not developing people, et cetera, et cetera. So, so I'm really on the watch out for that. Um, so yeah, what happened? So why were those people who passed that interview test with me then not bringing in talent to Stripe?

I think that the answer is one, they, well, first of all, as you know, well, you, even if you ha, I mean Stripe, when I first started, barely just had a couple of recruiters. So I was the

 for all of my early hiring. So one is some executives, if you're pretty early on, have never had to actually do the recruiting process.

 They do not know, and Like they're used to showing up in a conference room and there's a candidate sitting there. Yeah. So that's number one is maybe they don't know how to recruit, which of course I talk to them about and teach, try to teach them. Uh, number two is that's just because they've been in a more scaled environment.

Uh, number two issue may be that we just read them completely wrong and they have no followership. Right? And followership is a sign of strong leadership. There are people who want to come work with you. If you've had a long enough career, you should be able to pick up them. I'm not saying they should all get hired, by the way, Stripe.

You know, even if I had someone, I was like, they're the best person I've ever worked with. We put 'em through the ringer. But, you know, I brought people into the company. And by the way, not just for my function, I brought them in in, in a lot of different places. And I think that's because Stripe is great, but I also would like to think it's because people wanted to keep working with me, right?

So did they somehow not inspire followership? And did we miss a flag that they're just not a compelling leader? Right? The third thing is a little like almost. A variant of that, which is, are they not happy at Stripe? Like, do they not know how to, uh, sell the opportunity or convince people on the company?

Is it because they don't see it, they don't get it? Is it because they're not thriving? And often I think that was what was going on is they weren't adapting, um, in, into Stripe effectively. And therefore we're unable to sort of call someone and be enthusiastic. Um, I don't know. I don't know. Believe me, if I had the answer, it would be a chapter and the hiring chapter in the book is actually quite long.

But, but I didn't do enough introspection in the book on sort of what goes wrong when you're, um, trying to hire, it's like the, the initial leader onboarding is so fraught, right? And how do you handle that? I do talk a lot about leader on onboarding, but the, the reality is you can do a great onboarding process that it's probably gonna last about, you know, three months maybe.

And most of the problems happen after that. Three months.

 So a bunch of things to sort of. Dig in on one is when you think about what you're looking in terms of foreign talent from raw ingredients, so not like the difference between you're hiring a revenue leader versus an ops leader and the differential skill sets, but like when you get down to sort of the threads that tie the very, very best people that you've ever hired, are there, are there sort of common traits?

And then if I were to talk to you after an interview and you thought that someone had those, like what is going through your brain and like what are you pulling at to get at that outside of the obvious, really important sort of functional area expertise that somebody needs to have.

 Yeah. Yeah. I mean, I think at the highest level, I mean, I, I have this expression where I say, is the person a learning organism? But like, are they curious? Are they a learner? Are they interested in getting better? Um, which is different than by the way, a certain type of ambition is like, are they interested in success?

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Claire Hughes Johnson spent seven years as the COO of Stripe, overseeing rapid growth as the company scaled from under 200 employees to over 7,000. She takes us behind the scenes at some of the most pivotal moments in her own life and career that catapulted her into the deeply curious leader she is today.