Annie Pearl is Corporate Vice President of Copilot Product at Microsoft AI, where she leads product strategy and execution across Microsoft’s Copilot experiences. Previously, she led product, engineering, and design for Azure Experiences, overseeing developer platforms and AI infrastructure. Her team launched Azure Copilot, advanced Microsoft Learn for the AI era, and strengthened Microsoft’s startup ecosystem and developer relations communities.

Annie brings more than 17 years of technology leadership experience across startups and global enterprises. Before Microsoft, she was Chief Product Officer at Calendly and Glassdoor, led Enterprise product teams at Box through its pre- and post-IPO phases, and was a founding member and VP of Product at Xpert Financial. She began her career as a lawyer and management consultant before moving into technology. In 2026, she was named one of the Most Inspiring Women of San Francisco.