Annie Pearl

Chief Product Officer Calendly

Annie Pearl is the Chief Product Officer at Calendly, where she oversees the product vision, strategy, and roadmap for Calendly’s product. Annie is responsible for leading and scaling the product management and UX teams to deliver best-in-class scheduling experiences for users. Annie Pearl brings nearly 15 years of experience at startups and enterprise organizations, most recently as Chief Product Officer at Glassdoor overseeing the product, UX, and content moderation teams. Before that, she led Enterprise Product Management teams at Box both before and after the company’s IPO. Earlier in her career, she was the VP of Product and a founding member of Xpert Financial. She is a Board Member of WorkRampWell Health, and holds several advisory roles. Annie Pearl has a Juris Doctor from Santa Clara University School of Law and a Bachelor of Arts from Claremont McKenna College. She is a recipient of the 2019 San Francisco Business Times Most Influential Women in Bay Area Business.