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Clyde's Executive Power Lunch With Alibaba's John Caplan


What does the world’s largest online B2B marketplace and the platform democratizing access to quality extended warranty programs for merchants and customers alike have in common?

Besides John Caplan, that is?

Both businesses are built on the backs of strong teams. 

The strength of a team has never been more important for businesses in the eCommerce space. It’s an ideal time to be building an eCommerce business but the landscape remains decidedly competitive. For that reason, finding long-lasting success is impossible without a solid team.

For our first Executive Power Lunch, we brought together John Caplan, Clyde board member and’s President of North America & Europe and Brandon Gell, Clyde’s CEO and cofounder. The pair discussed the characteristics of a great team, how to build one through hiring, and how to lead one with your board and advisors.

Our own very Maddie Buras, Clyde’s Marketing Director, moderated the conversation, but if you couldn’t make it live, we’re here with a recap of what we talked about. And we’ll be having more of these conversations—from executive 1-on-1s to industry deep dives—including a behind-the-scenes look at Data Science on Tuesday, March 9th. Stay tuned to Clyde’s social channels and blog for more details in the coming weeks. 

The 3 requirements of a successful startup team

Be customer obsessed

At Alibaba, every employee, from a salesperson in Europe to an engineer in China to a product person in San Francisco, has to spend four hours a month interviewing customers and typing up what they’ve learned. 

That first seemed like overkill—Alibaba has thousands of employees!—but then it made sense.  Successful businesses are ones that deliver real value to customers.

“Literally every business that exists can spend more time on [customers],” said Brandon. Here are some ways Brandon and John talked about doing that:

  • Make sure your sales, marketing, and product teams are connected. “Hearing from customers their needs, and digesting and interpreting that input with the product organization to refine the marketing messages, can really help,” said John. “Sales folks having a seat at the table [is] a gift of actually being vocal about the value we're creating and providing real feedback.”

  • Serve the unserved customers. Part of Clyde’s differentiator in the warranty space is because we serve two customers: merchants, which have long been the main customer of the industry, but also the end consumer, who has long had to deal with complicated claims processes. “But the real way that you deliver the most value to the market—which is how you win the market—is to actually...spend all your time focusing on what the consumer actually wants and what that consumer experience is like,” said Brandon. “For us at Clyde, that’s product.”

Be inclusive and caring

Inclusivity at work can look like small, specific things, like John’s example of not using Zoom backgrounds in order to show his team the reality of his life (even if that includes his in-law walking in with a peanut butter and jelly sandwich during a meeting). 

But it’s also about investing in processes that make inclusion the default and leading with a genuine sense of care. Some examples:

  • Ask for regular feedback. John shared that Alibaba’s HR leader has every new hire make a presentation after 90 days at the company about how the onboarding process can be made better for the next cohort of new hires. “If everyone is inventing with a goal towards caring, the outcome can be pretty great,” said John. 

  • Be transparent. The whole Clyde team saw the pitch deck used as we were raising our Series A, and that’s just a small example of making everyone feel included. “It really creates a team that is oriented around sticking around through successes and [failures],” said Brandon. 

  • No fake care. Regular town halls, new hire buddy systems, social justice initiatives—all of those are great ways to show your employees that you are there for them. But only if you actually mean it. “It’s not, ‘Oh, we’re supposed to care, what should we do?’” said John. “If you actually care, do the things that a caring person will do.”

  • Make the space. Brandon’s cognizant of the openness that a communication tool like Slack can provide, and makes sure that more sensitive conversations—including ones about politics—don’t happen there in ways that make people feel excluded.

Grow at the right pace

John has a simple rule for whether his teams can invest in expanding: if they’re growing at 100% year-over-year, sure thing. If not, not yet. “Companies sometimes grow too fast, or hire too many people,” he shared. Here’s how to figure out whether your team is right-sized or not:

  • Set KPIs on velocity and impact. If you double the size of your product team but you’re releasing the same amount of new products as before, what’s going on there? “It's about momentum, and not getting stuck in your scale to slow you down,” said John.

  • Make sure that new people are caught up. Do your new hires know where you’ve been, where you’re going, and exactly how they fit in? “If not, you end up pulling instead of pushing,” said Brandon. “The only lever that I have or that any leadership has is making sure that our people are driving in the right direction.”

  • Stay small enough to be agile. The content marketing team at Alibaba completely shifted how they did business during the pandemic, going from putting out a piece once a week to publishing new stories multiple times a day on everything from fundraising to change management. That was only possible, said John, because that team was small and could pivot immediately.

How to hire a great team

Before you can build a business through a strong team, you first have to staff it. How can you separate the okay-but-not-great candidates from the people who will truly drive your success? John and Brandon had a few ideas to share:

  • Look for values, not skills. Skills can be taught. Values can’t. That means looking for grit and determination first, and then seeing if they meet your other shared values like Alibaba’s “no smart jerks” policy (to weed out the people you wouldn’t want to sit next to on a long-haul flight to China) or their “trust makes everything simple” mantra. 

  • Passion over product. Brandon was convinced that everyone he hired needed to be some kind of product person. Then he realized that he could live without a stable full of product superstars, but that he couldn’t live without a curious, passionate team. “I always ask, ‘What are you doing, what are you reading, what are you listening to?’ If the answer is ‘I’m not doing anything, I just want to make money,’ it’s like ‘Okay, you’re probably not the right person,’” said Brandon, who is looking instead for natural curiosity, even if on a subject he knows nothing about (see: heavy metal). 

  • Set a process. “If you’re not organized going in, what you get coming out is not really going to work,” John said. For his team, that means doing team interviews with four or five interviewers, each measuring something different.

  • Reference checks are crucial. “Even when someone is reluctant—people just want to say nice things—that’s one area to probe and find out,” said John. 

On leading a company authentically

“What you think building a company is, and the reality of building a company, are two different things,” said John. It’s not all high-stakes coding and legal battles in well-appointed conference rooms (or whatever else The Social Network implied). 

To lead well, CEOs need strong teams, as we’ve discussed. But that goes not just for their employees, but for their boards and their advisors, too. “The role of the board is to provide support to the leadership team,” said John. “It seems sort of basic, but it’s just to ask questions and have a conversation in an incredibly safe way.”

John, who calls himself an almost-unemployable lifelong entrepreneur, had three pieces of advice for CEOs starting out. Even if you’re not fortunate enough to have him on your board, we’re happy to share those with anyone else trying to build something cool:

  1. Focus on customers.

  2. Be your authentic self.

  3. Operate like your pants are on fire.

If you can do all of that, he said—if you can be “a joyful warrior building your business”—then you can get through anything, including a year of economic uncertainty, COVID, and social unrest. You, too, can be, as John said so well, “A customer-centric island of goodness and a great place for the humans that gather there on this noble mission.”

For a full recording of our webinar, click here .