Jessie Woolley-Wilson

Chair, Chief Executive Officer and President, DreamBox Learning

Jessie Woolley-Wilson is Chair, CEO & President of DreamBox Learning. Prior to joining DreamBox, Woolley-Wilson held several executive positions in leading EdTech companies including, Kaplan, LeapFrog SchoolHouse K-12 division and Blackboard’s K-12 Group. Woolley-Wilson supports the broader K12 industry by serving on the boards of several educational organizations including Rosetta Stone, Newsela, International Association for K12 Online Learning (iNACOL), the Woodrow Wilson Foundation, Western Governors University Board of Trustees and Islandwood. The New York Times has profiled Woolley-Wilson and her leadership style. Woolley-Wilson holds an MBA from Harvard Business School and a BA from the University of Virginia.