Annie Pearl

Annie Pearl is Corporate Vice President of Copilot Product at Microsoft AI, where she leads product strategy and execution across Microsoft’s Copilot product. Prior to Copilot, Annie led product, engineering, and design for Azure Experiences at Microsoft, focusing on developer platforms and AI infrastructure. Her team launched Azure Copilot, bringing agentic capabilities to cloud operations, evolved 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 served as Chief Product Officer at Calendly, helping scale the platform during a period of rapid growth to establish the platform as a market leader. She also served as Chief Product Officer at Glassdoor where she helped shape the product vision for millions of job seekers and employers worldwide. Earlier in her career, Annie led Enterprise product