Calendly’s evolution from scheduling tool to meeting engagement platform

Barb Mosher Zinck Profile picture for user barb.mosher September 6, 2023
Scheduling a look at Calendly's changing identity...


Calendly was founded ten years ago by Tope Awotona. At the time, he was in sales, and one of his biggest challenges was scheduling with prospects and customers. Calendly, a scheduling automation platform was his answer to this challenge. But Awotona’s vision for Calendly has come a long way in ten years, shifting from a simple scheduling tool to a meeting engagement platform for SMBs and enterprises alike. 

I spoke with Stephen Hsu, Chief Product Officer at Calendly, about the company's increasing focus on the enterprise, including several new features announced for enterprise customers and the thinking beyond basic scheduling. 

A focus on sales, customer success, and recruiting 

Calendly serves over 20 million users, from 'solopreneurs' to big enterprise teams, but its sweet spot remains sales, customer success, and recruiting. Hsu argues that as more advanced capabilities were added to the platform (including workflows and integrations) over the years, it was natural that salespeople wanted to use these tools with their teams. 

At the same time, there was also a shift in the way companies sold, from the single salesperson to what Hsu calls a “collaborative selling model” where you have a team of people, including SDR, BDR, AE, and Customer Success, involved in a sale. With this new approach to selling came the need to integrate with systems of record. 

Calendly is not the only platform offering scheduling capabilities. That said, the hardest ones to solve have very complex scheduling scenarios, and they come from Calendly’s three core personas. One example Hsu cites is a financial services customer who asked Calendly to open its APIs so they could call them from Appian (a business process management solution) to integrate Calendly with Microsoft Dynamics. 

Calendly has realized over the last couple of years that it is becoming a critical business process. Before that, they were doing straight integrations with CRMs. Customers were making these types of requests, Hsu recalls, and the firm recognized the opportunity.

Building for the enterprise

Calendly is introducing new enterprise features that build on Calendly as a critical business process.

Connectivity enhancements

Calendly has announced a number of connectivity enhancements to support enterprise customers. Along with integrations with over one hundred technologies, including CRMS, Zoom, and Greenhouse (applicant tracking), Calendly also has a Developer Portal, which enables enterprises to use Calendly APIs to create custom integrations and connect with other internal tools.

Improved routing

A lot of customers were trying to use Calendly’s APIs to get a lead from the website to a particular SDR or AE. These were homegrown solutions or through partnering with another technology. So Calendly decided to build their own capability because lead routing is essentially scheduling. 

This routing capability comes as a form that customers can configure through integrations and APIs to move that lead through Pardot or Marketo and then Salesforce, getting assigned to a rep's Google or Microsoft schedule. The Pardot integration is new, and the Marketo integration now includes syncing meeting data. Calendly has also improved Salesforce-lookup filtering to match known leads with the right sales rep.

Hsu explains: 

Calendly is in a unique position here because we sit on multiple calendars and systems of record. There's a start-up founder, Parker Conrad. He described something called a compound startup, which is basically a feeding experience layer that sits on all these systems of record that are siloed off. And so we sit on top of a calendar, we sit on top of the CRM, we sit on top of an ATS.

We sit on a bunch of different systems, but ultimately all that data surfaces in a scheduling layer because so many of so many external facing users like salespeople or recruiters rely on this data, but they're all kind of siloed off in these clunky databases. So we provide this one experience that you can manage the integrations and then schedule, and so it's just more of, like, efficiency and productivity.

Bringing all employees under a single domain account

As a product-led growth company, Calendly still sees a lot of viral growth within enterprise companies. That means there are different people in a single company using separate instances of Calendly, even though they are using the same domain. 

To address this, Calendly built Domain Control - the ability for an admin to bring these separate instances into the same instance. Employees can also request to join this IT-managed account. Hsu provides a few benefits to using a single instance:

  • It supports IT governance, which is critical in enterprise companies
  • It allows people to discover each other and collaborate. For example, a salesperson hiring can collaborate with an HR recruiter to get a candidate into the pipeline. 
  • Group people together (Sales, Recruiting, Marketing) to support improved discoverability and collaboration.

AI capabilities improve scheduling

A lot of Calendly's plans involve bringing more data into the platform, hence all the integrations. Microsoft Dynamics will soon be integrated, and they are doing some enhancements to Zapier to support SMB mid-market companies. Hsu explains that with all this data plus the ten years of meeting data, Calendly is working on some AI tools to help make it easier for users to schedule meetings using generative AI. These tools aren't available yet but are expected to go public beta next month. He says: 

So if you and I are on an email thread together, and Nicole's there, too, and was like, 'Hey, let's meet up next week', our Chrome extension will be able to read the context of that email thread and then provide the availability for all three of us. It will pull up all of our existing event-type infrastructure and the number of people in it, and then if we know that we all use Zoom, it'll say, 'We'll do this on Zoom' too. And then in that email experience, it’s like let's just book it right there, instead of having to go back and forth like that.

From scheduling tool to meeting engagement platform

Calendly is building its version of collaboration across departments, but it's a big change from what many people know it to be - scheduling calendars. Hsu says that they have to be careful how they make the shift to a meeting engagement platform because going too fast might overwhelm people. But other solutions are offering some of these capabilities, so going too slow will put them behind: 

I think a lot of people, rightly so, perceive Calendly as a calendar solution. Yes, most of the letters are in our name. So that is not surprising, and we have views of the calendar. But I think what's transforming for us right now is that we're less a calendar solution. We're more of a like, how do you have a successful meeting solution? In some of the capabilities that are coming out now in the next several months, you'll see us transform into a people-centric meeting-centric solution, versus a calendar solution. We just happen to have calendars as an integration point.

According to Hsu, Calendly has the advantage of being at the top of the meeting funnel - scheduling is the primary pain point they solve. So they already have mindshare, and they have customers doing a lot of these integrations on their own already. They will continue to build partnerships and do some organic development that directly brings the necessary features and capabilities into the platform, transforming Calendly into a true meeting engagement platform.

My take

A survey Calendly did of its customers revealed saving nearly 35 days and $21,000 in scheduling costs per year. That shows the power of automation. The new enterprise routing, connectivity, and meeting analytics features demonstrate Calendly's intentions toward supporting enterprise customers. But they also haven't forgotten their primary base - SMB mid-market. Hsu shared a vision that shows how Calendly can support companies of all sizes and requirements. 

You wouldn’t think scheduling would be that big of a deal. But when you step back and think about trying to schedule a meeting with more than one person and everything that happens around that meeting, you start to build a better appreciation for what needs to happen and how a platform like Calendly can make it much more efficient and productive. 

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