Jessie Woolley-Wilson
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Jessie Woolley-Wilson is Chair, CEO & President of DreamBox Learning. Prior to DreamBox, Jessie held several executive positions in leading EdTech companies including, Kaplan, LeapFrog and Blackboard.
Jessie supports the broader K12 industry by serving on boards of several educational organizations including Rosetta Stone, Western Governors University, the Woodrow Wilson Foundation the International Association for K12 Online Learning (iNACOL), and Islandwood. She is also a board member for Boeing Employees Credit Union. Jessie has been a featured speaker at international events including TEDx Rainier, SXSWedu, and DENT.
Jessie is a two-time recipient of EdTech Digest’s EdTech Leadership Award for her work in transformative innovation in education. 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's leadership style.
Jessie holds an MBA from Harvard Business School and a BA from the University of Virginia. She is a HCF and a Pahara Fellows Moderator.
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