President & CEO // DreamBox Learning
Jessie Woolley-Wilson is Chair, President, and CEO of DreamBox Learning®, Inc., the company that pioneered Intelligent Adaptive Learning™—heralded as a “game changer” in the ed-tech sector by nationally renowned academic and technology experts. Jessie has nearly two decades of experience in K–12 e-learning and has held several leadership roles in prominent education companies.
Before joining DreamBox Learning, Jessie was President of Blackboard’s K–12 Group where she led the company’s growth for the virtual and blended online learning market. Prior to Blackboard, she was President of LeapFrog SchoolHouse where she established SchoolHouse as a leader in ed-tech and one of the fastest growing educational software producers in the U.S.; Jessie also held leadership positions at collegeboard.com the interactive division of the College Board, and at Kaplan, the leading test preparation company in the U.S.
As an ed-tech industry leader, Jessie serves on the boards of several educational organizations including the International Association for K–12 Online Learning (iNACOL), Camelot Education, and the Woodrow Wilson Foundation. Locally, she serves on the boards of IslandWood, an environmental learning center that connects children to the outdoors, and Seattle Venture Partners International. Jessie has also served as a member of the World Economic Forum’s Global Agenda Council on Technology and Education, and has presented at TEDx Rainier, SXSWedu, and DENT. She was awarded the 2015 Executive Excellence Award in the CEO of the Year categoryby Seattle Business Magazine; she was also on the Forbes “Impact 15″ list for being a disruptor of education, and was honored as a “Woman of Influence” by Puget Sound Business Journal for making an impact in the ed-tech industry.
Jessie has an MBA from Harvard Business School and a BA in English from the University of Virginia. She is a 2007 Henry Crown Fellow of the Aspen Institute.