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Throughout her life and career, Jessie Woolley-Wilson has been driven by a singular belief that all children need and deserve high-quality learning opportunities, regardless of who they are or where they live. She believes that by supporting great teaching and learning, everyone wins: kids, families, communities and the world. Jessie has worked in the education technology space for nearly 20 years to support school and district leaders to improve learning and life outcomes for K-12 students.
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. Today, DreamBox serves more than 3 million K-8 students and over 120,000 teachers. The company provided more than 350 million math lessons across the U.S. and Canada in 2018.
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, 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 she has been honored as one of 2018’s Top 100 Influencers in EdTech. Forbes placed her on its “Impact 15” list for being a disruptor in education and The New York Times featured Jessie in their Corner Office column. Regionally, Jessie has received multiple accolades for her leadership, including, Seattle Business Magazine’s 2015 Executive Excellence Award in the CEO of the Year category,
GeekWire’s 2019 Big Tech CEO of the Year award, and the Puget Sound Business Journal’s “Women of Influence” award.
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.