Jessie Woolley-Wilson

Jessie joined DreamBox Learning® in 2010 as Chair, President, and CEO. The startup software company had pioneered Intelligent Adaptive Learning™ in 2006 and began partnering with schools soon after Jessie joined. Thus far, DreamBox serves nearly 3 million K-8 students and approximately 120,000 teachers. The company provided more than 350 million math lessons across the U.S. and Canada in 2017.

Jessie recently secured a $130 million investment in DreamBox from The Rise Fund, a global impact investing fund managed by TPG Growth. Prior to joining DreamBox, Jessie served as president of Blackboard’s K-12 Group and LeapFrog SchoolHouse, the K-12 division of LeapFrog Enterprises. Jessie also served in leadership positions at collegeboard.com, the interactive division of The College Board, and at Kaplan, the leading test preparation company in the U.S.

Jessie supports the broader K12 industry by serving on the boards of several educational organizations including Rosetta Stone, Newsela, the Western Governors University Board of Trustees, and Ursuline Academy. She is also a board member for Boeing Employees Credit Union, Pacific Science Center, and The Bullitt Foundation. She has been a featured speaker at international events including TEDx Rainier, SXSWedu, DENT and GeekWire Summit 2018.

Jessie is a two-time recipient of EdTech Digest’s EdTech Leadership Award for her work in transformative innovation in education and honored her as one of 2018’s Top 100 Influencers in EdTech. Seattle Business Magazine awarded Jessie the 2015 Executive Excellence Award in the CEO of the Year category and Forbes placed her on its “Impact 15” list for being a disruptor in education. The Puget Sound Business Journal honored Jessie as a “Woman of Influence” and 425 Magazine named her as one of eight “Unstoppable Eastside Women” for having a clear focus on the greater good. Additionally, The New York Times has profiled Jessie and her leadership style in their Corner Office column.

Jessie holds an MBA from Harvard Business School and a BA from the University of Virginia. She is also a 2007 Henry Crown Fellow and moderator for the Aspen Institute.