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Jessie Woolley-Wilson
SaaS Innovator / Learning Technology Executive / GM / innovator; speciality in scaling companies
Jessie Woolley-Wilson is a prominent figure in the field of educational technology, currently serving as the President, CEO, and Board Chair of DreamBox Learning. With nearly two decades of experience in K-12 educational technology, she has been instrumental in driving innovation and improving learning outcomes for students.
Early Life and Education
Born in Texarkana, Texas, and raised in Wilmington, Delaware, Jessie attended the Ursuline Academy before pursuing higher education. She earned a Bachelor of Arts degree from the University of Virginia and later obtained an MBA from Harvard Business School in 1990.12
Career
Jessie's career began at Chase Manhattan Bank, where she worked in the Third World Debt Restructuring Group. She subsequently held positions at American Express and served as President of LeapFrog Enterprises from 2004 to 2005. Before joining DreamBox in 2010, she was the President of Blackboard's K-12 Group from 2007 to 2010.13 At DreamBox Learning, she has led significant initiatives, including securing a $130 million investment from The Rise Fund in 2018, making it one of the most well-funded education startups that year.3
Under her leadership, DreamBox Learning has developed an Intelligent Adaptive Learning™ platform that has received over 40 awards and is utilized by more than 500,000 teachers and six million students across North America.34 In 2023, DreamBox was acquired by Discovery Education, expanding its reach to a global audience.3
Awards and Recognition
Jessie Woolley-Wilson has received numerous accolades for her contributions to education technology. She is a two-time recipient of EdTech Digest’s EdTech Leadership Award and was named one of Forbes' "Impact 15" for her disruptive work in education. Additionally, she has been recognized as one of the "Top 100 Influencers in EdTech" and received several regional awards for her leadership.123
Board Memberships and Speaking Engagements
In addition to her role at DreamBox, Jessie serves on various boards, including those of Rosetta Stone and Western Governors University. She is also a Henry Crown Fellow at the Aspen Institute and a moderator for its discussions. Jessie is a sought-after speaker at major conferences such as TEDx Rainier and SXSWedu.23
Her commitment to educational equity is evident in her belief that all children deserve access to high-quality learning opportunities, regardless of their background.3