Innovators of Color

Jessie Woolley-Wilson


DreamBox Learning

Jessie is president and CEO of DreamBox Learning. Prior to joining DreamBox, Jessie held executive positions in leading EdTech including, Kaplan, LeapFrog SchoolHouse and Blackboard's K-12 Group. Jessie supports broader K12 industry serving on boards for educational organizations including Rosetta Stone, Western Governors University Board of Trustees, and Ursuline Academy. She was a featured speaker including TEDx Rainier, SXSWedu, DENT and GeekWire Summit. She is a two-time recipient of EdTech Digest's Leadership Award, and 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 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".