Unlocking Learning Potential with Dreambox

DreamBox Learning is an exciting company that provides engaging, individualized and, yes, effective learning experiences for young students. This nimble technology infuses fun into learning and delights students, parents and teachers alike. For years, education technology has existed on the periphery of instruction, often providing after-the fact, rear-view perspectives on a child’s progression. Today, we know we need more: real time, personalized data that shapes the individual learner’s educational path and guides them toward mastery. This is what we do at DreamBox. Our K-3 math curriculum impacts learning at the point of instruction, and in doing so, unlocks learning potential in all learners at all levels – regardless of zip code or background. This is transformative and will help to reshape the future of learning in the US and abroad.

At DreamBox, we are closing the gap between the way students live and the way they learn by leveraging new adaptive technologies that promote student success. I am thrilled to be joining such a talented and committed team. I look forward to participating in future dialogues with school administrators, teachers, parents and students to grow this company so that more and more students can benefit from the unique DreamBox Learning experience.


Jessie Woolley-Wilson
CEO DreamBox Learning

Jessie Woolley-Wilson

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 to improve learning and life outcomes for K-12 students.

Jessie joined DreamBox Learning® in 2010 as Chair, President, and CEO. The startup software company had pioneered Intelligent Adaptive Learning™ in 2006 and began partnering with schools soon after Jessie joined. Today, DreamBox serves nearly 3 million K-8 students and approximately 120,000 teachers. The company provided more than 350 million math lessons across the U.S. and Canada in 2017.

Jessie recently secured a $130 million investment in DreamBox from The Rise Fund, a global impact investing fund managed by TPG Growth. Prior to joining DreamBox, Jessie served as president of Blackboard’s K-12 Group and LeapFrog SchoolHouse, the K-12 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 K12 industry by serving on the boards of several educational organizations including Rosetta Stone, Newsela, the Western Governors University Board of Trustees, and Ursuline Academy. She is also a board member for Boeing Employees Credit Union, Pacific Science Center, and The Bullitt Foundation. She has been a featured speaker at international events including TEDx Rainier, SXSWedu, DENT and GeekWire Summit 2018.

Jessie is a two-time recipient of EdTech Digest’s EdTech Leadership Award for her work in transformative innovation in education and honored her as one of 2018’s Top 100 Influencers in EdTech. Seattle Business Magazine awarded Jessie the 2015 Executive Excellence Award in the CEO of the Year category and Forbes placed her on its “Impact 15” list for being a disruptor in education. The Puget Sound Business Journal honored Jessie as a “Woman of Influence” and 425 Magazine named her as one of eight “Unstoppable Eastside Women” for having a clear focus on the greater good. Additionally, The New York Times has profiled Jessie and her leadership style in their Corner Office column.

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 for the Aspen Institute.
Jessie Woolley-Wilson