Jessie Woolley-Wilson, Chair, CEO & President, DreamBox Learning
Throughout her life and career, Jessie Woolley‑Wilson 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. She believes that by supporting great teaching and learning, everyone wins: kids, families, communities and the world. Jessie has worked in the education technology space for nearly 20 years to support school and district leaders in efforts to improve learning and life outcomes for K‑12 students.
Jessie joined DreamBox Learning in 2010 as president and CEO. The start-up software company had pioneered Intelligent Adaptive Learning in 2006 and began partnering with schools soon after Jessie joined in 2011. DreamBox currently serves nearly 2.2 million K-8 students and approximately 80,000 teachers, and provided over 255 million math lessons in the 2015-2016 school year across the U.S. and Canada.
Prior to joining DreamBox Learning, Jessie served as president of Blackboard’s K‑12 Group and president of LeapFrog SchoolHouse, the e‑learning division of LeapFrog Enterprises. Jessie also served in leadership positions at collegeboard.com, the interactive division of the College Board, and at Kaplan, the leading test preparation company in the U.S.
Jessie supports the broader K‑12 industry by serving on the boards of several educational organizations, including the International Association for K‑12 Online Learning (iNACOL), Camelot, the Woodrow Wilson Foundation, and Islandwood. Jessie has been a featured speaker at international events, including TEDx Rainier, SXSWedu, and DENT. She was awarded the 2015 Executive Excellence Award in the CEO of the Year category by Seattle Business magazine. She was also on the Forbes “Impact 15” list for being a disruptor of education, and was honored as a “Woman of Influence” by Puget Sound Business Journal for making an impact in the EdTech industry. Jessie was also recognized by 425 Magazine as one of eight “Unstoppable Eastside Women,” for having a clear focus on the greater good.
Jessie holds an MBA from Harvard Business School and a BA from the University of Virginia. She is also a 2007 Henry Crown Fellow and moderator of the Aspen Institute.