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Jessie Woolley-Wilson

Chair, CEO & President

Jessie Woolley-Wilson is President and CEO of DreamBox Learning®. 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...

Roles at DreamBox Learning

  • Chair, CEO & President

    Current role


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