With Henry Ward and Tope Awotona
Helping people schedule meetings, Henry said, is so simple—but Calendly turned it into a business with millions of customers. “People had been struggling with this for a long time,” he said, so there were scheduling products already out there. But they were hard to use. “In the early days, we just really bid on simplicity.”
Easy scheduling was great, but customers also wanted to solve their real problem. How could Calendly help them achieve the outcome of those meetings? So for the last six years, they’ve created tasks and insights that connect to business outcomes, like revenue growth, customer attention, and customer satisfaction.
Tope’s advice to founders facing a lot of competition: “Take a very, very strong position very early on about why you’re differentiated. What are you doing differently that makes people willing to bear the switching costs—to go from however they’re solving that problem today to using your product or your service?”
Take a very, very strong position very early on about why you’re differentiated. What are you doing differently that makes people willing to bear the switching costs—to go from however they’re solving that problem today to using your product or your service?
Calendly’s first differentiator was simplicity. The second was price. Calendly deliberately launched 100% free, only introducing paid plans after about two years. The third differentiator, Tope said, was “Power. That power came in the form of pre- and post-meeting workflows—automating the tasks around the meetings.”
“Founders, by default, love winging it and getting things done. But when you have 700 people, it’s important that everyone is aligned.” So Calendly changed as it scaled, adopting a detailed three-year strategy doc with specific ways to measure their progress.
Change is also about rejecting complacency. “If I, and the executive team, are acting as though we’ve made it, and we just need to kick back and reap the rewards of the work we’ve done—that feeling permeates throughout the organization. But I don’t feel that way at all,” he said, nor does the rest of the team. “It’s incredibly rare to be a part of creating something that millions of people use. Soon enough, billions of people will use the product in some form or fashion. I could have never imagined I would have that opportunity. It’s an incredible responsibility to see it to its greatest form.”
Tope sees his role as setting the vision. He’s very passionate about some parts of the business. For others, he just wants to know that it’s being done well, and that he and his team agree on what success looks like. “What I’m evaluating when I hire people is that I can trust that they understand—that when I’m not in the room, they’re making great decisions. And by the way, 99% of the time, you’re not in the room.”
What I’m evaluating when I hire people is that I can trust that they understand—that when I’m not in the room, they’re making great decisions. And by the way, 99% of the time, you’re not in the room.
One thing that keeps both Tope and Henry going is what they learn from their teams. “I’m so happy to not be the smartest person at Calendly,” Tope said. “My role today is less having the best ideas, but being the editor of the ideas.” The best value he can provide is sharing what he knows about the customer journey and letting executives make trade-off choices of their own.
“Everything seems bigger up close,” Tope said. “I had many moments in which I thought, ‘This is gonna crush the business.’” In the grand scheme of things, those problems will probably resolve themselves.
But nobody knows what the next year or so will look like, so staying thoughtful is key. “We should err on the side of being very conservative with our assumptions and being prudent,” recognizing that customers are looking to do more with less right now and finding opportunities to help.
“People who will tell me what I need to hear, not what I want to hear. That’s the most difficult thing in our roles. People don’t want to upset you or disappoint you. It’s important to create an environment that allows people to give you candid and honest feedback that you need to hear, and deliberately, seek those people out.”
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