Jessie Woolley-Wilson

President & CEO

DreamBox Learning

Jessie Woolley-Wilson is President and CEO of DreamBox Learning®. Prior to joining DreamBox, she held executive positions at leading EdTech companies, including Blackboard, LeapFrog, and Kaplan. She has been a featured speaker at TEDx Rainier, SXSWedu, and the ASU GSV Summit, and Ernst & Young named her “Entrepreneur Of The Year®” in the Pacific Northwest region. She has supported the broader education community by serving on several boards, including Quizlet, Rosetta Stone and the Western Governors University Board of Trustees. She holds an MBA from Harvard Business School and a BA from the University of Virginia.