Power of Women

Jessie Woolley-Wilson

President & CEO

DreamBox Learning®

When Reed Hastings of Netflix led the acquisition of DreamBox Learning® —a very promising, first-of-its-kind digital math company— through The Charter School Growth Fund in 2010, he set out to hire a truly visionary leader with extraordinary operating strengths. That person was Jessie Woolley-Wilson. She was the President of Blackboard’s K-12 Division and President of Leapfrog Schools Division before that. Now 12 years later, Jessie has been at the helm of DreamBox, driving it to substantial scale serving over 6 million students and 400,000 teachers with over 1.5 billion lessons completed.

In 2021, Jessie led DreamBox to broaden the product lines to include reading through the acquisitions of Squiggle Park and Reading Plus, making DreamBox the only provider of solutions rated “Strong” by Johns Hopkins’ EvidenceforESSA.org in both mathematics and reading. That year Evergreen Coast Capital also acquired a majority stake in DreamBox. TPG’s The Rise Fund retains a significant minority stake in the company.

Jessie has supported the broader education community by serving on several boards, including Quizlet, Rosetta Stone, and the Western Governors University Board of Trustees.