Jessie Woolley-Wilson

Jessie Woolley-Wilson is the former CEO and president of DreamBox Learning and brings over 20 years of experience in K12 EdTech, having also served as President of Blackboard K12 and LeapFrog SchoolHouse. After selling DreamBox Learning to Discovery Education in 2023, Jessie joined Owl Ventures as Operating Partner. She also serves on other education boards including Quizlet, Presence Learning and Discovery Education. Jessie also serves as board Trustee at Western Governor’s University, the Pahara Institute and The Aspen Institute. Jessie is a two-time recipient of EdTech Digest’s “EdTech Leadership Award” for her work in transformative innovation in education, and she has been named one of 2018’s “Top 100 Influencers in EdTech.” ASU GSV honored her with the “Innovator of Color” and “Power of Women” awards. Forbes honored Jessie as a “50 Over 50” honoree for her innovation in education, and The New York Times featured Jessie in its Corner Office column. She has also been featured in CNBC, NPR, and Business Insider, among other leading news publications. Jessie holds an MBA from Harvard Business School and a BA from the University of Virginia. She is a 2007 Henry Crown Fellow and moderator for the Aspen Institute.