Jessie Woolley-Wilson is Chair, President and CEO of DreamBox Learning®, the company that developed the Intelligent Adaptive Learning™ platform heralded as a “game changer” in the eLearning sector by nationally renowned academic and technology pundits. Jessie brings nearly two decades of experience in K-12 e-learning and education technology to DreamBox Learning. Throughout her career in the education industry, Jessie has held several leadership roles in general management, sales and marketing, operations, and business development.

Before joining DreamBox Learning, Jessie was President of the K–12 Group at Blackboard where she led the company’s growth and development for the virtual and blended online learning market. Prior to Blackboard, she was President of LeapFrog SchoolHouse, the schools division of LeapFrog Enterprises, where she established SchoolHouse as a leader in education technology and one of the fastest growing educational software producers in the United States.

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

As an education industry leader, Jessie serves on several boards for nonprofit organizations including the International Association for K-12 Online Learning (iNACOL); Editorial Projects in Education, which publishes Education Week; the Education Innovation Network; Camelot For Kids; the Software & Information Industry Association (SIIA); and Technology Access Foundation (TAF). Jessie has also served on the