Jessie Woolley-Wilson
President, Blackboard K-12
As President of Blackboard's K-12 Group, Jessie Woolley-Wilson brings more than fifteen years experience in the education industry to Blackboard. In her role, she oversees Blackboard’s growth and development strategy focused on elementary and secondary education. Jessie brings a tremendous amount of knowledge and experience in helping schools implement technology programs that positively impact student learning.
Prior to joining Blackboard, she served as President of LeapFrog SchoolHouse where she was instrumental in establishing SchoolHouse as a leader in education technology and as one of the fastest growing educational software producers.
Throughout her fifteen-year career in the education industry, Jessie has held several leadership roles in general management, marketing, and business development. She has extensive experience managing start-ups, turnarounds, and high-growth environments. Prior to joining LeapFrog, Jessie was Vice President of Marketing College Solutions at collegeboard.com, the interactive division of The College Board. In addition, Jessie was part of a three-member executive team that built MyRoad.com, an e-learning company that helped middle school, high school, and college students prepare for college and careers, before it was acquired by The College Board in 2001.
Jessie began her career in education at Kaplan, where she held roles as Regional Area Director of the Southern California Test Prep Service Centers and Executive Director of Pre-College and Pre-Graduate testing programs. She was also President of Crimson & Brown Associates, a diversity recruiting firm and Kaplan's first acquisition in the career industry.
Jessie received her MBA from the Graduate School of Business at Harvard Business School and her BA in English from The University of Virginia. She is a 2007 Henry Crown Fellow of the Aspen Institute and is on the Board of the National Education Association Foundation, Junior Achievement of the National Capital Area and the Partnership for 21st Century Skills. Jessie most recently was appointed to the World Economic Forum’s Global Agenda Council on Technology and Education. The World Economic Forum is an independent international organization committed to improving the state of the world by engaging leaders in partnerships to shape global, regional and industry agendas.