How Calendly is building a platform by turning scheduling into a center-stage event

The tools you use most often are the ones you think about the least. Calendly, an app that helps people plan, schedule and follow up on meetings, may be a perfect example of that.

Today, some 10 million people send Calendly links to millions of others to sort out meeting slots. But perhaps because its purpose is to get people from one step to the next in their day, and from using one piece of software to the next, Calendly tends not to get much attention.

That was the case, at least, until last year. The COVID-19 pandemic sent many of us home to work, and as commutes were cut out and people couldn’t meet at work, we suddenly found ourselves in a meeting frenzy. Calendly came into its own, and investors took notice.

“We are seeing strong usage in spite of the changes in how people work for the simple fact that human connection and collaboration are ultimately what drives a business forward.”

Created out of founder Tope Awotona’s need for a tool to organize his life better, Calendly by nature kept a low profile even as it grew. But the combination of pandemic-fueled growth and major funding effectively changed that overnight. Earlier this year, we explored how the Atlanta-based company came virtually out of nowhere to raise $350 million at a $3 billion valuation.

That’s a heavy load to lay on a founder and a startup, and it was the starting point of our fireside chat at TechCrunch Disrupt 2021. If the product works well, how do you take it to the next level — and frankly, why should you?

“The question I had at the time [of that funding round] was, will the company take it as a distraction and become enamored with the publicity that comes with that? Or will we stay focused and continue to work really hard for our customers and partners and ourselves?” Awotona said. “Nine months later, it’s very clear that we’ve done the latter. Our culture and values have more or less remained the same.”

The company continues to stay focused on the “prosumers” who fueled its growth. These are individuals who gravitated to Calendly not because their company mandated it, but because they may have been sent a link for a meeting by someone else, became impressed with the UX, and started using it themselves — the classic kind of virality that has spurred a lot of technology to ubiquity.

Alongside that focus on prosumers, Calendly is also doubling down to build tools to address groups of users — starting from teams and going all the way up to large organizations.

“As a matter of fact, one of the fastest-growing segments of our business is the enterprise segment; the customers that pay us over $100,000 a year,” Awotona said. (Calendly doesn’t break down the share of enterprises in its paying customer base.)

However, enterprise users and prosumers are the same when it comes to the basics, Awotona said. “Even when we go into midmarket and enterprise customers, it’s still ultimately the end users that that take us in there, and it’s still the end users that we seem to make really happy,” he said. “The way we grow is to start with individual users.”

However, in a more practical sense, building for groups presents a new set of challenges and opportunities. It brings a deeper focus on security and building tools that help larger teams coordinate as well as individuals can on Calendly, and so these are now a large part of the startup’s product development focus.

The company is also taking a deeper approach by building services that cater to specific verticals and specific types of users. While sales people — who arguably live and die by how many meetings they have — are some of Calendly’s biggest and earliest adopters, the company is building experiences that fit more naturally with what other professionals, like teachers, service professionals and researchers, might want out of a meetings-and-scheduling tool.

Other startups have also focused on planning and booking for specific verticals: Fresha and Booksy are two of many in the beauty sector; Doctolib is among the options for medical professionals; and ServiceTitan targets home services professionals and contractors. Building for specific verticals may put Calendly into competition with any number of such alternatives, but it also brings potential acquisition and consolidation targets.

Calendly’s position as a more general meeting and scheduling platform is interesting in that regard. We spoke at some length about whether Awotona sees Calendly’s service as a feature or a platform.

It’s a big question for software entrepreneurs, investors and, to an extent, end users, too. “Feature” implies a limit to the amount of development that there is left to do on the product, as well as its extensibility and ability to be independent longer term. “Platform” is, well, somewhat the opposite of that — there’s a ring of ambition to it, though features can still be critical and extremely valuable. Both carry their own kinds of risks.

Awotona told me he sees Calendly as a platform, a very service-oriented one, which is not just about how it will bring more services on to its own platform — you can already launch your Zoom meetings from there, and build integrations with other apps. Rather, it’s how Calendly is also used elsewhere, which can let it become a repository of all your meeting activity.

“Calendly is becoming a platform in the sense that we have many, many partners who have taken our APIs and use them to enhance their products,” he said. “For them, that’s an exciting extension of their platforms. And I think that’s the definition of a platform.”

This could also help Calendly stave off significant competition not just from other meeting and scheduling startups, but also massive tech platforms like Google and Microsoft that also play in this space (even as their products also integrate and play nice with Calendly).

Awotona draws from the lessons of other products when he thinks about how his company might fare in a David versus Goliath scenario when I ask him whether Google Calendar feels like a threat:

We think about competition to the extent that, you know, we feel an urgency to serve our customers. Well, when we do that, we naturally box out the competition and make their lives difficult. I really like the Google Calendar example, because yet another product that Google offers is Google Forms, for free. But in spite of that, Qualtrics is a multibillion dollar company. And think about SurveyMonkey. There’s power with focus. When you focus singularly on the problem with scheduling or surveys, for example, you’re able to build a much more complete solution. And you have this understanding of the customer and the end user that allows you to be efficient with your solutions and solve the most notable problems. That’s the same parallel that we see for Calendly. When we talk to our users, they say we have the most complete product on the market, and that’s our goal.

Longer term, like any other startup, Calendly will also need to contend with consumer and business habits and how they are changing. The company definitely saw spikes in usage and adoption at the start of the pandemic — two hockey-stick-shaped growth charts that definitely contributed to its changing fortunes.

Awotona says there was less of that than you might think, though.

“We are seeing strong usage in spite of the changes in how people work for the simple fact that human connection and collaboration are ultimately what drives a business forward,” he said. “And so whether those meetings happen virtually or they happen in person, the value proposition of Calendly was strong before the pandemic, it’s strong during the pandemic, and will remain strong after the pandemic.”

But will users want to keep meeting in any format? Or will other software and/or business practices come along that remove the need for this altogether?

Pointedly, Awotona reiterated the idea that using Calendly can lead to more than just a meeting.

“We’ve never taken a position that more meetings are better, right?” he said.