Jessie Woolley-Wilson

Jessie Woolley-Wilson serves as an Operating Partner at Owl Ventures and a Senior Advisor at TPG The Rise Fund, providing guidance to Venture Capital and Private Equity firms since December 2022. Woolley-Wilson is also a Board Member at Quizlet and a Board Advisor at Class, contributing expertise to various educational technology initiatives. From April 2020 to April 2024, Woolley-Wilson acted as an Advisor for GSV Capital Partners, supporting VC investors and C-suite executives. Previously, Woolley-Wilson was the President & CEO of DreamBox Learning, a leader in Intelligent Adaptive Learning for K-5 math education, and held roles including Board Member at Rosetta Stone, President of K12 at Blackboard, and President of LeapFrog SchoolHouse. Woolley-Wilson began a career in education leadership at LeapFrog Enterprises as EVP of Education & Training. Educational qualifications include an MBA from Harvard Business School and a BA in English from the University of Virginia.