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Calendly welcomes new Chief People Officer: Jeff Diana

Caitlin Brett, September 18, 2020

Calendly has experienced rapid growth in both its customer base and its talent despite the challenges of 2020. The number of Calendly employees has grown from 82 at the end of 2019 to 182 in September 2020, on a trajectory to reach more than 200 before the end of the year.

To continue to nurture its blossoming employee culture, Calendly has named Jeff Diana to the role of Chief People Officer in this latest expansion of its executive team. Jeff lends more than two decades of experience to Calendly’s strategic vision, having previously served as a consultant to Calendly as well as many other high-growth pre-IPO software companies and venture partners.

“Calendly is a special place indeed — our mission, our people, our culture, and our product are second to none,” Jeff wrote in an email to the Calendly team shortly after the announcement was made. “I’m honored to join the team and I look forward to achieving even more incredible heights as we change how the world connects and works together.”

Prior to joining Calendly, Jeff was the Chief People Officer at Atlassian. He was responsible for HR, Real Estate, Employee Experience, and Shared Services worldwide. Jeff was instrumental in driving a successful IPO and growth agenda over four years, enabling Atlassian to go from 300 team members and $100M in revenue to 2000+ and over $600M in revenue.

Earlier in his career, Jeff was CPO at SuccessFactors, an SAP company, as well as Chief HR Officer at Safeco, a personal insurance company. Jeff has also held various HR leadership roles at Microsoft, General Electric and Bell South.

Join our team! Curious about our open positions, company culture, and perks and benefits? Learn more at Careers at Calendly.

Caitlin Brett biography
Caitlin Brett

Caitlin Brett is a senior copywriter, content marketing professional, and Calendly alum. Learn more at

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