Jessie Woolley-Wilson

President and 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. Ms. Woolley-Wilson brings nearly two decades of experience in K–12 eLearning and education technology to DreamBox Learning. Throughout her career in the education technology industry, Ms. Woolley-Wilson has held several leadership roles in general management, sales and marketing, operations, and business development.

Before joining DreamBox Learning, Ms. Woolley-Wilson 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. As an education technology industry leader, Ms. Woolley-Wilson serves on several boards for non-profit 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; and the Software & Information Industry Association (SIIA). Ms. Woolley-Wilson has also served on the World Economic Forum’s Global Agenda Council on Technology and Education.

She was recently named as a “2012 Woman of Influence” by The Puget Sound Business Journal as well as recognized as a “Best Leaders to Watch” in 2011 by EdNET. Ms. Woolley-Wilson 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.