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Scaling Startups with Stripe’s Claire Hughes Johnson

After joining a 160-person startup in 2014 as COO, Claire Hughes Johnson later found herself fielding countless questions about how exactly she helped Stripe co-founders Patrick and John Collison scale to more than 7,000 people.

Now a corporate officer and advisor at Stripe, Claire has bundled all of those strategies, frameworks, and memories into a book, “Scaling People: Tactics for Management and Company Building.” The textbook-like guide also draws on many of the lessons that Claire learned in her nearly 11 years at Google, which at one point included leading a 2,300-person sales team with a $11 billion quota. 

Based on our conversation with founders and leaders at GGV portfolio companies, read on for some of Claire’s best advice—and check out her book for 1,000-plus other topics related to scaling yourself and your teams:

Create—and document—your startup’s operating principles

“It's one muscle to get product-market fit,” Claire says. “Building the product, testing with users, iterating, figuring out the opportunity, getting a team behind that, and marching through what I think probably feels like wilderness sometimes to get there is an amazing skill set. And guess what? It's not the same as building a company.

During this critical company-building phase, start with documenting your startup’s beliefs, values, and operating principles. For Claire, she begins by building self-awareness.

From Myers-Briggs to DISC and other personality type tests, Claire typically dedicates 25% of a daylong planning meeting to leadership assessments and conversations about ways of working, which are “important but never urgent. If you do not carve out the time to do this work for yourself and with your team, you will pay a price. You will just not pay it tomorrow.” 

Don’t assume you need to add experienced executives right now

Founders and CEOs at startups with under 150 employees can find themselves in the “uncanny valley,” or where they struggle to draw experienced executives and operators from established tech companies. Will a person who is accustomed to bigger teams and more resources be able to adapt? 

In reflecting on her own career trajectory, Claire says her post-college experience of working on “very scrappy, very entrepreneurial” political campaigns trained her well for high-growth startups. But if a startup brings in someone who hasn’t been a builder, you can expect “a lot of organ rejection,” Claire says, adding that an executive from a FAANG company is likely to be a fish out of water if your startup’s infrastructure isn’t ready. 

So when is the right time to add an experienced exec to your leadership team? Consider bridging the gap with “someone who can give you a few years of building or an up-and-comer,” Claire says. When evaluating an executive’s impact, she also suggests tracking telltale signals like:

  • Is this person attracting any talent in the first three months? (Are people following him or her to your startup?)
  • Is this person adding observations about gaps in talent? (Is this person then recommending people to recruit?)

To attract and retain employees, Claire recommends going beyond compensation, benefits, and perks—“have a good parental leave policy, but you do not need laundry service”and focusing on these three areas instead:

  • Purpose: Does this person feel like he or she is working on something that matters?
  • Mastery: Is this person learning? Do you consistently invest in him or her with stretch assignments?
  • Autonomy: As Claire says, “the reason that many people go to a startup is to get more learning and responsibility. That’s why I did.”

Build a solid operating system for every team

As you’re building self-awareness, you should also be building a repeatable operating system for every team. This may include fundamentals like: 

Establishing a communication cadence: Rituals and traditions like all-hands meetings and 1:1 meetings can “create some solid ground within which chaos and ambiguity can exist,” Claire says. When it comes to distributed workforces and return-to-office policies, “be intentional about what you choose. Build systems and processes around [that] … People don’t organically collaborate well across time zones. Time zones aren’t going away.” 

Carving out space for in-person collaboration: If scaling globally, you may find yourself with a leadership team spread across multiple countries and regions. Claire recommends budgeting for in-person collaboration every quarter and regularly monitoring: “Does my team need more in-person time?” 

Creating prioritization frameworks: Claire recalls that in her first month or so at Stripe, she drew up a list of priorities knowing that “I will get three done if I’m lucky.” As she learned, it’s equally important to align on what projects fall below the line.

Developing systems to unblock your teams: Fast-moving teams can lose momentum when disagreeing on who does what and when. “When you’re hitting friction or are blocked, it is not weakness or failure. It is how to make the system better,” Claire says. She suggests processes like writing up both perspectives and escalating to the decision maker who is the “common node” (or the person who everyone ladders up to). 

Embrace the difference between managers and leaders

Philosophically, Claire believes that most people grow up with a natural tendency to lean one way or the other, calling herself “more naturally a manager. I’m very organized. Give me a goal. I will figure out how to get there.”  

For some people, being a leader can be uncomfortable because “you are setting a vision and demanding things that you don’t know if it’s possible. You’re turning up the heat. I want more, better, faster.”

As a leader, it’s also your job to address the existential threats (i.e. tech debt) that others are not talking about. By setting the standard, you’re “going to say an unpopular thing,” Claire says. “It’s like making kids eat vegetables. You have to lead people through it.”

Ask yourself: 

  • Do you know how to adapt your leadership style to show up differently at times? 
  • How do you flex on that continuum?

Remember: As a founder, your job is to try to get people to go somewhere they don’t see. You may never fully achieve that vision, but you still have to convince people that the mission is worth tackling.

“Culture eats strategy for breakfast,” Claire adds. “How do you get the work done? What do you agree on as a collective? Build those norms—that's what is really going to matter.”