As President, K12 at Blackboard Inc., Jessie Woolley-Wilson brings more than 15 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.  Woolley-Wilson 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 15 year career in the education industry, Woolley-Wilson 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, Woolley-Wilson was Vice President of Marketing College Solutions at collegeboard.com, the interactive division of The College Board.  In addition, Woolley-Wilson 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.

Woolley-Wilson 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.

Woolley-Wilson 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 boards of Junior Achievement of the National Capital Area and the Partnership for 21st Century Skills. 

Woolley-Wilson serves on the World Economic Forum’s Global Agenda Council on Technology and Education, an independent international organization committed to improving the state of the world by engaging leaders in partnerships to shape global, regional and industry agendas.  Most recently, she was appointed to the Board of Editorial Projects in Education Inc. (EPE).  EPE publishes Education Week, American education's newspaper of record, the Teacher Professional Development Sourcebook, Digital Directions, edweek.org, teachermagazine.org, and TopSchoolJobs.org.  Their primary mission is to help raise the level of awareness and understanding among professionals and the public of important issues in American education.