Operator Spotlight

Meet Stripe Corporate Officer, Advisor, and former COO Claire Hughes Johnson

Caroline Caswell

“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

This month, we spoke with Claire Hughes Johnson, longtime advisor and founding LP to OpCo, and as a member of the Board of Advisors frequently supports our PortCos on operational excellence. She is a corporate officer and advisor at Stripe. Previously, Claire was Chief Operating Officer from 2014 to 2021, helping the company grow from fewer than 200 employees to more than 7,000. At various times, she led business operations, sales, marketing, customer support, risk, real estate, and all of the people functions, including recruiting and HR. Prior to Stripe, she spent 10 years at Google leading business teams, including overseeing aspects of Gmail, Google Apps, and consumer operations, as well as serving as a vice president for AdWords, Google Offers, and Google's self-driving car project. She serves on the boards of Ameresco, the Atlantic, Aurora Innovation, and HubSpot. She’s the author of Scaling People: Tactics for Management and Company Building - out now! 

Having been in senior operations leadership seats for over a decade, how have you seen the COO role evolve over time? How do you think it may change in the future? 

I think the COO role is the most unknowable role on the executive team. I find myself fielding questions about it a lot. I’m not going to say I’m an expert, other than having been a COO. 

In the bigger picture of businesses, it's actually not a very prominent role, if you look at the Fortune 1000, for example. In fact, it's a role that over the last decade has decreased slightly. COO is not always a common choice, and I don't think it should be thought of as such. The context in which I was a COO is a more common one, which is when you're a younger company, recently founded in a high-growth or even a medium-growth moment, where your CEO, who is often your founder, is having to simultaneously build the product and the company and the business. The combination of building the product and the company is a lot for one or even two founders to do. It is a tremendous amount of work to foundationally deliver and be there for your customers externally and be there internally, and you haven't yet built all of the structures and the teams.

When I first joined Stripe, I like to joke that one of my jobs was as a recruiter. I really was. I was the head of recruiting and I was the head of people and I was the COO. We didn't have any of that in the stack yet. We had some fantastic recruiters, by the way, one of whom ended up running recruiting. But I needed to get in there at multiple levels to help with the scale, so I was less of a layer than an actual contributor in multiple dimensions. You want to be really aware of when the role is that versus when the role is an operating layer that is a complementarity. And here, the reality is it's both.

To the question of how I think it will evolve: I think the more that the CEO is really self-aware, which is one of my themes in Scaling People, and understands where they’re best positioned to spend their time and where they have blind spots or need someone who's going to more deeply devote themselves to certain parts of running the company or the business, that self-aware CEO hopefully finds someone and has a structure that meets the strategy of what they need to build for the next five to 10 years. In those cases, you're going to have a very successful partnership that may evolve into something different over time, as all companies should. But COOs will always be a critical potential tool that you use, especially when you're having to build fairly rapidly. If done well, I think it gives you an acceleration and foundations that you might not have gotten to build if you were trying to do it all on your own. But thinking the COO is going to solve all your problems—unfortunately, they're not. Because you have to be there at the table too. 

Also, as your company matures, which has been the case for Stripe, you could actually elevate those individual functions and organizations. And you probably should. And I hope whoever is your COO will help you recognize, “Hey, maybe I shouldn't run all of these things.” I've also seen some different twists on it, which I like seeing. I coach and mentor a few COOs; some of them are more classically focused on go-to-market and some of them are more internally-focused. More recently, I've seen a few that are more product- and technical-focused, and I want to see more of that too.

That's really the theme of what I'm saying: As your company evolves, as it grows, if you're not assessing who is at the table, in which seat, and what role should I play as the CEO or the founder, what role should this individual play, you're doing your company a disservice. Because growth is dynamism and dynamism means change. If you get too wedded to your particular seat at the table, you may miss opportunities that might be how you build the next stage.

What’s a leadership lesson you experienced during hypergrowth at Stripe that surprised you? 

So many lessons. I think one lesson is when people tell you “You’ve got to look around the corners, what you’re doing today you’re going to need more people to do in six months, think about planning for that growth”—one, I think if you have any measure of humility or paranoia, which a lot of us do, especially Stripe’s founders, you don’t want to get ahead of yourself. You don’t want to overhire, you don't want to assume success. That’s a natural reaction. But even though I knew that, even though I knew I should be hiring myself out of a job, we did not develop enough talent internally. We did invest, but never enough. Nor did we hire externally at the right moments. There was a point where I think I had 23 direct reports, which, if I had given myself advice walking in the door, I would've said, “Never do this.” That wasn’t great, because that meant I had no time to think. I wasn't thinking around the next corner.

There was also a version of this that happened to us as a company. At the time, I was responsible for annual planning and getting our strategy together for the next year. We tried to delegate that to people we perceived to be leaders in the company. I think we didn't delegate very well, first of all, but we ended up micromanaging a bunch of people writing a bunch of plans, and I don't think that felt good for them. It certainly didn't feel good for the leadership team. When I look back on it, it just wasn't fair. Like, they weren't well positioned to know the bigger picture of where their work fit, and we hadn't communicated enough of the strategy to them. The lesson overall is whatever process you're building—your planning process, your goal-setting process—it’s got to match where you are at that moment.

That was, to me, a version of never getting where you know you need to go fast enough. Maybe you don't have all the people, but you might also be either over-rotating toward certain processes or under-rotating. It’s like a Goldilocks problem. What you just have to decide is when am I really, really going to try to get it right, versus when to give yourself some grace and make some trade-offs. Especially when you're in a high-growth environment, if you’re looking for perfection, you'll be so beaten up by the end of every day you will not be able to execute at all. You'll either be frozen seeking perfection or you'll be exhausted and unable to really function because you cannot do it all. You’ll burn out. 

There’s someone who had been at Stripe when I was fairly early in my role who then went on to another company in a more senior role that was similar to my role at Stripe. She called me and was like, “Oh my gosh, how did you live with everything being broken all the time?” I laughed and said, “Well, you do have to get used to it.” It’s painful, because you're looking at something and you're like, “This is not good for everyone.” You can't achieve perfection, but you can't give up on it. The Jedi move is to be able to say that to the company: “I get that this part is not perfect, and it's painful, and you're all complaining about it. We are not going to fix it this year. We're going to do it the way we designed it, and then next year we're going to be better. Give me your feedback and we'll iterate.” 

I think the other thing leaders do is think they have to solve it all for everyone. Actually, the most effective company is one where people feel ownership for everything that is affecting them in the organization and build a way for people to make things better with you. I think I sometimes didn't do that enough.

What’s a piece of advice you would give to yourself 10 years ago, if you had the opportunity? 

10 years ago? That was when I was deciding to join Stripe! 

Ten years ago I was at a stage in my career where I was getting interesting opportunities and I really had to get in touch with who I was and what I was good at and what I wanted, not what an image of me might be to others, which can be a strange phenomenon. One of the tenets of the book is “Build self-awareness to build mutual awareness with your team.” Building self-awareness is key, because you’re going to be more effective as a leader and a manager, but you’re also going to manage your career more effectively. 

What I liked when I was talking to John and Patrick about joining Stripe was how much they were seeking to know me and what I viewed my strengths to be. At the time I was getting recruited by some companies that were putting me in central casting, like, “You will run all the things that we don’t want to run.” And I said, “Well, I'm not necessarily good at all those things. Let’s talk about what I think I'm good at, where I can add value, where I might not, where I might need to learn.” I was really working hard to understand what I wanted. 

The other thing that happens—and I think this happens every decade or so of my career—is your ambition starts to change. Part of this is aging, I guess, but your ambition is like, “What is success? What is important to you? What mark do you want to leave on the world?” I think it’s important to be really in touch with the fact that what is important to you and what success is to you is not the same as other people, and also it will change, and that's okay. Some people expect everyone to be going for the same brass ring, and that's not really what success is. I felt fortunate that I got to start to make choices later in my career, but also I felt lucky that I took the time to think about what those choices really meant. 

What makes a great leader?  Can great leadership be learned?

I do think leadership can be learned. I think management definitely can be learned. A lot of management is hard to learn because it happens behind closed doors. You’re not in someone else's 1:1s or in their performance reviews. The book tries to demystify that and say, “This what happens behind those closed doors,” or “This is what you might say and what the other person might say.” In my early career, I had the chance to shadow people or practice conversations with people. I thought it was hugely beneficial. I still do that with some hard conversations: I play them out with someone I trust.

Leadership is a little bit different. Management is a lot about systems and people and talent and caring about them, and matching the work with the individuals and monitoring the work. Leadership is about culture and setting ambition and setting vision and, frankly, sometimes making people uncomfortable. I would say I came to management more easily and I was less comfortable as a leader. To be a really effective leader, you have to push people and make them uncomfortable and ask them to do things they don't think they can do. That wasn't a natural ability of mine, and I had to practice that. 

I remember leading a pretty big team at Google, and my direct reports were preparing some presentations that were important for our strategy. They came in and presented them to me, and I just didn't feel like they brought their A game. I was like, “Well, I'm glad they feel comfortable showing their drafts to me, but this is important.” And then I happened to see a lot of them in a similar environment with a colleague of mine, and they brought their A game. I had to look at myself and say, “Why did I not set the bar high enough? Why is my team doing better work for this other person? What is that person doing that I'm not doing?” 

There was a question in Google's employee engagement survey, and now in Stripe’s, which is effectively about high expectations. Does your manager have high expectations and set a high bar? I would say that my bar at Google was not always consistently high, and it has been the entire time I've been at Stripe. So that means I learned something. I learned something about being supportive and being empathetic but also setting the expectation and the vision in a more aspirational and ambitious way. It took me time to get there, but I got better work out of people. There's a reason you work at it, which is to get results.

Operating leaders are often juggling multiple demands on their time. How do you manage your time and balance competing demands?

Managing time is a lifelong obsession of mine. 

My mother was a very successful student and ended up at Radcliffe and then at Harvard for her PhD. I asked her about the decision to pursue a PhD, and she said, “There’s a point in your life where you realize you get to choose between time and money, and I chose time. I wanted an academic career because I wanted time to think and do my work, and I wanted my summers off.” What stuck with me was less the time-money trade off—which may or may not be true—but more that controlling your time is controlling your wealth. It’s all you have.

I've heard a lot of people say that the most successful founders tend to be quite protective and controlling of their time. I'm not always successful at that, but what I am good at is, if I have to get this thing done, I have thought way in advance about how long it's going to take me, when certain things need to be done. It’s not just because I'm obsessive about hitting milestones, it's that I don’t want to end the day in a difficult situation, mentally or physically. So I have a calendar in my head of, “What's it going to take? What do I need to protect in my time? Who do I need to involve? How do I get from A to B? What is the clock that is required?” 

It’s a control-freak thing a little bit, but it's because I'm controlling my most precious resource. I'm preserving my mental health by planning, and planning gives me a sense that I can accomplish things. So, how do I balance all these competing responsibilities and different teams that need different things? I try to partner with people who help me manage my calendar, but that’s about being very clear. Frankly, I do this for the whole year: what are my top priorities and goals for the quarter, for the month, for the week?

People who've worked closely with me know that I have a lot of Post-Its, which feels very old-school, but it's because every week I write a Post-It that I put on the front of my notebook—yes, I take written notes: These are the top three things I need to get done this week. And I'm looking at it every day, and I am chastising myself if I'm not spending time on those three things. I also write, each day, the thing that is most important that I get done. Because otherwise my time just gets consumed by one-on-one meetings or whatever. Sharing a list of what I need to carve out time to do with someone who helps me do that has become a way that I operate. But it's also a way that I create balance, because I'm not feeling stressed that I won't have time to get it done. 

I think the mistake we all make is we're too generous. We give up time that we've been protecting. So don’t do that. Also we’re not realistic about what work is really going to take. I think that's been my biggest lesson: I never allocated enough time early on. Now I've come to respect that it takes a lot to get real work done. I'm never going to be perfect at protecting my time, but that's a skill that I think you can hone. Own your calendar. 

I think there's an assumption—and this is one of the really good things about the Valley that wasn't true when I lived in DC and worked there—that people will help other people, knowing it will lead to a virtuous cycle. But how do you balance that? 

I think my default is to say yes because I have seen that generosity from others and I want to repay it to others. And it does come back. You never know how someone comes back into your life. So, how do you manage saying yes and also having to protect your time? I think the answer is you cannot actually say yes to everything. 

I've worked with some people who will get a request and they'll say, “What exactly do you need from me?” And they'll essentially make it more efficient. So instead of saying, “Let's have a half-hour meeting,” or “Let's do a phone call,” they'll get the specific ask and try to answer it asynchronously or point to a resource or introduce them to someone. I think you need to learn how to triage: Is this something I could answer over text, or give them a book or an article to read, or introduce them to someone? 

I think the other way is, you might say yes to something but you might not do it for a few weeks. You might look at your list and think about the time you're protecting and say, “I want to help you, but can you wait to have this conversation?” And often people can.

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