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Jessie Woolley-Wilson serves as Operating Partner at Owl Ventures, the leading EdTech VC in the world. With nearly $3B assets under management, Owl is one of the largest VCs dedicated to investing in software companies serving the global EdTech sector. From 2010-2023, Jessie served as President and CEO of DreamBox Learning® before selling it to Discovery Education. Prior to joining DreamBox, Jessie held executive positions at multiple leading EdTech companies, including Blackboard, Leapfrog, and Kaplan.
Jessie is a two-time recipient of EdTech Digest’s “EdTech Leadership Award” for her work in transformative innovation in education, and she has been named a “Top 100 Influencers in EdTech.” Forbes placed her on its “Impact 15” list for being a disruptor in education, and The New York Times featured Jessie in its Corner Office column.
Jessie is a 2023 Forbes 50 Over 50 Honoree and Jessie has received several industry and leadership awards, including Seattle Business Magazine’s Executive Excellence Award in the “CEO of the Year” category, GeekWire’s “Big Tech CEO of the Year” award, Puget Sound Business Journal’s “Women of Influence” and “Innovator of the Year” awards, and the Ernst & Young “Entrepreneur Of The Year®” award in the Pacific Northwest region.
Jessie serves on several boards, including Quizlet, Discovery Education, Charter School Growth Fund, and class.com. She also serves as Trustee at The Aspen Institute, the Western Governors University Board, and the Pahara Institute. Jessie has been a featured speaker at many events, including TEDx, SXSWedu, DENT, GeekWire Summit, and the ASU GSV Summit.
Ms Woolley-Wilson holds an MBA from Harvard Business School and a BA from the University of Virginia.
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