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Annie Pearl

Chief Product Officer

Before Calendly, Annie led Glassdoor’s product vision and user experience for job seekers and employers around the world. She has led enterprise product teams at Box, including before and after its 2015 IPO, and was the VP of Product and a founding member of Xpert Financial. Annie was honored as one of the Most Influential Women in Bay Area Business in 2019 by the San Francisco Business Times. She holds a J.D. from Santa Clara University School of Law and a Bachelor’s degree from Claremont McKenna College. She loves spending time outdoors, especially skiing, hiking, and running.


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Roles at Calendly

  • Chief Product Officer

    Current role


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