Calendly at $270M ARR

TL;DR: Sacra estimates that Calendly hit $270M in annual recurring revenue (ARR) at the end of 2023, up 46% year-over-year, as they push into the enterprise and fend off challenges from the bundles of Microsoft and Google. For more, check out our full report and dataset on Calendly.

Key points via Sacra AI:

Calendly (2013) replaced the traditional email back-and-forth around scheduling meetings with a shareable link that displays the sender's availability and allows recipients to book a time slot directly, growing to $40M in 2019 and accelerating through COVID to $125M ARR by 2021. Calendly grew to 20 million users in 200+ countries through an viral organic growth loop—users signing up for Calendly after receiving a scheduling link themselves—that enabled highly capital efficient growth (just $550K raised to get to $60M ARR).
Calendly has continued to grow close to 50% year-over-year at $100M+ revenue scale, hitting $270M ARR at the end of 2023, by integrating into hardcore B2B workflows that write to the calendar like sales (CRM), recruiting (ATS), and marketing (MAP). Compare to sales & marketing tools with in-built scheduling apps like HubSpot (NYSE: HUBS) at $2.5B ARR, up 20% year-over-year, Outreach at $250M ARR at the end of 2023, up 11% year-over-year, and Gong at $285M ARR, up 43% year-over-year.
Google and Microsoft are weaponizing their bundlenomics with GSuite and Office 365 and existing distribution & engagement with Google Calendar and Microsoft Outlook by building in native calendar booking to commoditize Calendly. At the same time, Calendly has moved upmarket to the enterprise, capitalizing on its strong bottom-up adoption in large organizations—with users in 86% of Fortune 500 companies—and leveraging its cross-functionality across different productivity suites and systems of record.

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