Jessie Woolley-Wilson is the President, CEO, and Board Chair of DreamBox.
[1] Born in Texarkana, Texas, and raised in Wilmington, Delaware,[2] Jessie studied at the Ursuline Academy, then joined the University of Virginia where she received a Bachelor of Arts in English, then earned her M.B.A from Harvard Business School.
[5] She sits on the board of directors of Rosetta Stone and other education organizations.
[3][5] In 2012, Jessie was named one of Forbes' Impact 15 in education for her work at DreamBox.
Regionally, she received many accolades and awards for her leadership roles, including the Seattle Business Magazine's Executive Excellence Award in 2015 in the CEO category, and GeekWire’s 2019 Big Tech CEO of the Year.