Jessie Woolley-Wilson

Jessie Woolley-Wilson is President and CEO of DreamBox Learning®. Prior to joining DreamBox, Jessie held several executive positions in leading EdTech companies including, Blackboard’s K-12 Group, LeapFrog SchoolHouse and Kaplan.

Jessie supports the broader education community by serving on several boards including 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.

Jessie 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 and The New York Times featured Jessie in its Corner Office column. Regionally, Jessie 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.