Jessie Woolley-Wilson

Jessie Woolley-Wilson is a learning innovator, speaker, and EdTech pioneer, who currently advises venture capital investors and C-suite leaders in their portfolio companies. She has spent more than two decades in the educational technology industry, and was previously President and CEO of DreamBox Learning®. Prior to joining DreamBox, Woolley-Wilson held several executive positions in leading companies including Blackboard’s K-12 Group, LeapFrog SchoolHouse and Kaplan.

Woolley-Wilson supports the broader education community by serving on several boards including Quizlet and Class, and formerly, Rosetta Stone, the Western Governors University Board of Trustees, and Ursuline Academy. She has been a featured speaker at events including TEDx Rainier, SXSWedu, DENT and GeekWire Summit, and is a Trustee of the Aspen Institute.

Woolley-Wilson is a two-time recipient of EdTech Digest’s Leadership Award and was 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, as well as their "50 Over 50: Innovation" list, and The New York Times featured her in its Corner Office column. Regionally, Woolley-Wilson has received multiple accolades, including Seattle Business Magazine’s Executive Excellence Award in the “CEO of the Year” category; GeekWire’s “Big Tech CEO of the Year” award; and the Puget Sound Business Journal’s “Women of Influence” award.

Woolley-Wilson holds an MBA from Harvard Business School and a BA from the University of Virginia.