Who Owns Calendly?

Tope Awotona founded Calendly in 2013 in Atlanta, Georgia. A former EMC salesperson, Awotona grew frustrated with the time-consuming process of scheduling sales calls through back-and-forth emails. He quit his job and poured his life savings, along with a small business loan, into building an automated scheduling platform.

Awotona initially hired Railsware, a software development company based in Kyiv, Ukraine, to build the first version of the Calendly platform. The product launched with a freemium model: basic scheduling was free, and premium features required a paid subscription. Calendly's first customer was BrightBites, an educational tools company that needed scheduling software for parent-teacher conferences. Teachers who used the tool began adopting it themselves, driving early organic growth.

In April 2014, Calendly raised $550,000 in seed funding from Atlanta Ventures. The company added premium tiers for individuals and teams that same year. For the next seven years, Calendly operated without additional external funding, relying on revenue growth to fund operations.

The COVID-19 pandemic dramatically accelerated Calendly's adoption. As remote work became widespread in 2020, demand for virtual meeting scheduling tools surged. Calendly's user base expanded rapidly as professionals, educators, and businesses needed efficient ways to coordinate online meetings.

In January 2021, Calendly raised $350 million in Series B funding at a $3 billion valuation. OpenView Venture Partners and ICONIQ Capital led the round. The funding made Awotona one of the few Black billionaire founders in the technology industry, according to Forbes. The company used the capital to expand its product capabilities, grow its workforce, and invest in enterprise features.

Calendly acquired Prelude, an interview scheduling platform, in September 2022. The acquisition added recruiting and hiring workflow capabilities to Calendly's product suite. In May 2021, the company also made a seed investment in Reclaim.ai, an AI-powered calendar management tool.

By 2024, Calendly employed approximately 650 people. The company has since reduced headcount to roughly 500 employees as of 2026. In May 2024, Awotona publicly set a goal of reaching $1 billion in annual revenue. To support enterprise growth, Calendly secured compliance certifications including SOC 2 Type II and ISO/IEC 27001, and aligned its platform with FINRA guidelines for financial services clients.

The company transitioned to a remote-first workforce model in 2021, closing its physical Atlanta office while maintaining Georgia as its official headquarters. Calendly continues to serve over 10 million users across 230-plus countries.