Calendly was founded in 2013 by Tope Awotona, a Nigerian-American entrepreneur who had previously worked as a salesperson at Dell EMC. Awotona was frustrated by the time wasted scheduling sales calls through back-and-forth emails and envisioned a simpler solution: a link that prospects could click to book time directly on his calendar.
Awotona founded Calendly with his personal savings and a small business loan, working out of the Atlanta Tech Village startup incubator. He hired Kyiv, Ukraine-based development firm Railsware to build the initial software platform. Calendly launched in 2013 with a freemium model, offering a free tier for individual users and paid plans for teams and enterprises.
Calendly grew steadily through the mid-2010s through word-of-mouth and viral sharing. The product's viral loop was inherent in its design: every time a Calendly user sent a scheduling link, the recipient was exposed to the product. This viral mechanism drove organic growth without heavy marketing spend.
In January 2021, Calendly raised $350 million in a funding round led by OpenView Venture Partners and Iconiq Growth at a reported $3 billion valuation. This was Calendly's first external funding round, remarkable given that the company had grown to significant scale without outside investment. The funding round made Calendly one of Atlanta's most valuable technology startups and one of the most valuable bootstrapped-to-funded companies in recent memory.
During the COVID-19 pandemic in 2021, Awotona closed the company's Atlanta headquarters and transitioned to a fully remote workforce, reflecting the shift to remote work that also drove demand for Calendly's scheduling tools.
In 2022, Calendly gained significant viral attention when a debate on Twitter about the etiquette of sending Calendly links (some users found it impersonal) led to widespread discussion and increased sign-ups. The controversy demonstrated the product's cultural penetration.
Calendly has continued to expand its platform with new features including routing forms (directing meeting requests to the right team member), collective scheduling, and integrations with CRM systems like Salesforce and HubSpot.