About
Jessie supports the broader K12 industry by serving on the boards of several educational organizations including the International Association for K12 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 has an MBA from Harvard Business School and a BA in English from the University of Virginia. She is a 2007 Henry Crown Fellow of the Aspen Institute. 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.
Position in the VCSift Database
- • 2 investors at DreamBox Learning are tracked.
- • 51 investors hold the CEO & President role in VCSift. Jessie Woolley-Wilson is one of them.
- • 1,032 investors are based in Seattle, Washington, United States.
Data sourced from 410,343 investor profiles. Updated June 2026.
Investment Focus
- Location
- Seattle, US
Contact Information
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