Jessie Woolley-Wilson ’81

Throughout her life, Jessie 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. After 20 years of working in education technology, Jessie joined DreamBox Learning® in 2010 as Chair, President, and CEO. DreamBox served more than 3 million K-8 students, over 120,000 teachers, and provided 350+ million math lessons across the U.S. and Canada in 2018.


Jessie holds a BA from the University of Virginia and a MBA from Harvard Business School. She is also a 2007 Henry Crown Fellow and moderator for the Aspen Institute.


Jessie serves on the boards of several educational organizations including Rosetta Stone, the Western Governors University, and Ursuline Academy. She is also a board member for Boeing Employees Credit Union, Pacific Science Center, and The Bullitt Foundation. Jessie has been a featured speaker at international events including TEDx Rainier, SXSWedu, DENT, and GeekWire Summit 2018. She is a two-time recipient of EdTech Digest’s EdTech Leadership Award for her work in transformative innovation in education and honored as one of 2018’s Top 100 Influencers, in addition to many other awards.