 Born in Texarkana, Texas, and raised in Wilmington, Delaware, 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.Jessie started her career at Chase Manhattan Bank, specifically working at its Third World Debt Restructuring Group, and later worked at American Express.Prior to joining DreamBox, she served as President of LeapFrog Enterprises from 2004–2005 and President of Blackboard Inc.'s K-12 Group from 2007-2010.