Jessie Woolley-Wilson

Trustee at Overlake Hospital Medical Center

Jessie Woolley-Wilson is President and CEO of DreamBox Learning®. Prior to joining DreamBox, she held executive positions at leading EdTech companies, including Blackboard, LeapFrog, and Kaplan. She has been a featured speaker at TEDx Rainier, SXSWedu, and the ASU GSV Summit, and Ernst & Young named her “Entrepreneur Of The Year®” in the Pacific Northwest region.

Jessie serves on the Board of Trustees for Rosetta Stone and Western Governors University.

She holds an MBA from Harvard Business School and a bachelor of arts degree from the University of Virginia.

Timeline

  • Trustee

    Current role

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