Jessie Woolley-Wilson is CEO & President of DreamBox Learning. Jessie brings nearly two decades of experience in K-12 eLearning and education technology to DreamBox Learning. Throughout her career in the education industry, Jessie has held several leadership roles in general management, sales & marketing, operations and business development. Most recently, Jessie served as President of K12 & K-20 Strategy at Blackboard where she led Blackboard’s growth and development strategy for the K12 group. Prior to joining Blackboard, she served as President of LeapFrog SchoolHouse, the schools division of LeapFrog Enterprises, where she was instrumental in establishing SchoolHouse as a leader in education technology and one of the fastest growing educational software producers in the U.S.

Jessie has also held leadership positions at collegeboard.com, the interactive division of The College Board; MyRoad.com, an e-learning company that helped middle school, high school, and college students prepare for college and careers; and Kaplan, the leading test preparation company in the US.

Jessie received her MBA from Harvard Business School and her BA in English from The University of Virginia. She is a 2007 Henry Crown Fellow of the Aspen Institute and serves on several boards of non-profit organizations, including the National Education Association Foundation, the Partnership for 21st Century Skills, the Ron Brown Scholars Program, and Editorial Projects in Education Inc. (EPE), which publishes Education Week. Jessie has also served on the World Economic Forum’s Global Agenda Council on Technology and Education, an independent international organization committed to improving the state of the world by engaging leaders in partnerships to shape global, regional and industry agendas.