Jessie Woolley-Wilson

Chair, President and CEO, DreamBox Learning

Jessie Woolley-Wilson is Chair, President and CEO of DreamBox Learning, the company that developed the Intelligent Adaptive LearningTM 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, the interactive division of the College Board;, 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 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 TAF Educational LLC. Jessie has also served on the World Economic Forum’s Global Agenda Council on Technology and Education. In 2012, she was named to the Forbes “Impact 15” list for being a disruptor of education and honored as a “Woman of Influence” by The Puget Sound Business Journal for making an impact in the education technology industry as well as the community.

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.

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