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Jessie Woolley-Wilson      

CEO, DreamBox Learning

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, 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 nonprofit organizations including iNACOL (International North American Council for Online Learning), Editorial Projects in Education (publisher of Education Week), the Education Innovation Network, Camelot For Kids and SIIA Software & Information Industry Association. Jessie has also served on the World Economic Forum's Global Agenda Council on Technology and Education. She was named a "Best Leaders to Watch" in EdNET's Best for 2011, a peer recognition program.

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.


Technology And Classroom Data
This piece was co-authored with Jessie Woolley-Wilson, CEO of DreamBox Learning. Gone are the days when the success of technology integration in ...
The Global Search for Education: Online Math Learning | The ...
I had the pleasure of interviewing Jessie Woolley-Wilson, the President and CEO of DreamBox Learning. Jessie has a long history with ed-tech (including work ...

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