Clockwise

Clockwise was founded in late 2016 in San Francisco by Matt Martin, Gary Lerhaupt, and Mike Grinolds, three colleagues who had worked together at RelateIQ (later SalesforceIQ), a relationship-intelligence CRM startup Salesforce acquired for roughly $390 million in 2014. Martin, a former Am Law 100 civil litigator turned engineer/product lead, became CEO; Grinolds served as the company's first CTO before departing around September 2020; Lerhaupt, a Stanford-trained computer scientist, later held the CTO title. The company's founding insight was that individual calendar apps optimize for one person's convenience while creating chaos across a team or organization -- Clockwise set out to apply machine learning to reschedule flexible ('moveable') meetings automatically so that teams could reclaim contiguous blocks of uninterrupted work time.

Clockwise moved from private beta to general availability in June 2019, coinciding with an $11 million Series A co-led by Greylock (John Lilly) and Accel, with participation from Slack Fund, Jay Simons, George Hu, Soraya Darabi, Ellen Levy, Michael Ovitz, and SV Angel -- bringing total funding at that point to roughly $13 million. In January 2020 the company launched what it billed as an AI scheduling assistant for Google Calendar, then closed an $18 million Series B in mid-2020 (announced June 2020), led by Bain Capital Ventures with partner Ajay Agarwal joining the board -- notably negotiated and closed largely during the early months of the COVID-19 pandemic. As remote and hybrid work accelerated demand for calendar optimization and burnout prevention, Clockwise raised a $45 million Series C in January 2022 led by Coatue, with Atlassian Ventures, Accel, Greylock, and Bain Capital Ventures participating, taking total funding to approximately $76 million. At that point the company reported having rescheduled over 4 million meetings and created over 2 million hours of Focus Time across more than 10,000 organizations, including named customers Netflix, Twitter, Coinbase, Atlassian, Asana, and Airtable.

In the AI-copilot era of 2023-2024, Clockwise leaned into its seven years of proprietary scheduling-engine development to differentiate from newer entrants naively wiring large language models directly to calendar APIs. In August 2024 it launched Prism, a free, natural-language AI assistant layered on top of its existing scheduling engine that lets users create, move, and bulk-manage meetings through conversational commands (e.g., 'reschedule my afternoon,' 'set up 15-minute 1:1s with these four people'), with CEO Matt Martin positioning the seven-year-old scheduling engine as the 'reliability layer' that keeps LLM-driven actions from breaking calendars. This launch came against a shifting competitive landscape: rival Reclaim.ai was acquired by Dropbox in August 2024, leaving Clockwise as one of the more prominent independent, venture-backed players in AI calendar optimization alongside newer entrants like Motion and Vimcal.

Business model

B2B SaaS sold on a freemium/tiered model -- free for individuals, paid Teams/Business/Enterprise plans sold on a per-seat basis to companies seeking organization-wide calendar optimization.

Subscription (per-seat SaaS pricing across free, team, and enterprise tiers); exact public pricing/ARR not disclosed in sources reviewed.