Owl Ventures, the largest EdTech venture capital firm globally with over $2 billion assets under management, announced the addition of Jessie Woolley-Wilson as Operating Partner. Jessie brings a wealth of experience to Owl Ventures and its portfolio companies as she has worked in the education technology space for over 20 years to support school and district leaders in improving learning and life outcomes for K-12 and higher education students. Jessie is driven by a singular belief that all learners deserve high-quality educational opportunities, regardless of who they are or where they live.
Jessie was most recently the CEO and President of DreamBox Learning, an Owl Ventures portfolio company since 2015 that was acquired by Discovery Education in 2023. In addition to being a former Owl Ventures portfolio company CEO, Jessie currently serves on the boards of Owl Ventures portfolio companies Quizlet and Class Technologies. In her new role, Jessie will have an integral role in sourcing and evaluating new investment opportunities for Owl Ventures, providing strategic guidance and mentorship to Owl’s portfolio companies, and actively participating on their boards. Jessie will be a valuable resource to the investment team and a trusted advisor to Owl portfolio founders/CEOs as they scale their businesses.
“Jessie is one of the great education entrepreneurs and leaders of our generation. She created enormous enterprise value alongside deep scaled social impact at DreamBox Learning”, said Tory Patterson, Co-Founder & Managing Director at Owl Ventures. “She is a values-driven mentor to many of us who have been working hard to evangelize and scale the power of technology to drive broad equity and access in education. She is a hero of mine, and I am deeply honored to now call her a Partner at Owl Ventures. I am most excited for the next cohort of founders and CEOs who will benefit from her established excellence in leadership and powerful network within the education industry as she works to scale the next wave of great innovation.”
“I was introduced to Owl Ventures in 2015 when Tory Patterson decided to make a bet on DreamBox Learning and me as a CEO”, said Jessie Woolley-Wilson. “As an Owl Ventures portfolio company, we benefited from the partnership and sage counsel of the distinguished team at Owl who offered us capital, K12 sector expertise, as well as invaluable insights on consequential operations, go-to-market, product innovation and financial matters — all while supporting our mission to radically transform the way the world learns. I look forward to beginning this new and exciting chapter as Operating Partner to help identify, fund and scale the next generation of innovative companies that will transform the EdTech landscape in the US and abroad.”
Jessie joined DreamBox Learning® in 2010 as Chair, President, and CEO. She worked closely with board members such as Reed Hastings and Tory Patterson of Owl Ventures. In 2018, she secured a $130 million investment in DreamBox from The Rise Fund, a global impact investment fund managed by TPG Growth, making DreamBox the most well-funded education startup that year. The company’s pioneering Intelligent Adaptive Learning™ platform has won more than 40 top education and technology industry awards and is used by more than 500,000 teachers and 6 million students across the US and throughout Canada and Mexico. In 2023 DreamBox Learning was acquired by Discovery Education, becoming part of a global learning platform with access to 45 million students and over 4 million educators.
Prior to joining DreamBox, Jessie served as president of Blackboard’s K-12 Group and LeapFrog SchoolHouse, the K-12 division of LeapFrog Enterprises. She also has held leadership positions at collegeboard.com, the interactive division of The College Board, and at Kaplan, the leading test preparation company in the U.S.
Jessie is a two-time recipient of EdTech Digest’s “EdTech Leadership Award” for her work in transformative innovation in education, and she has been named one of 2018’s “Top 100 Influencers in EdTech.” ASU GSV honored her with the “Innovator of Color” and “Power of Women” awards. Forbes honored Jessie as a “50 Over 50” honoree for her innovation in education, and The New York Times featured Jessie in its Corner Office column. She has also been featured in CNBC, NPR, and Business Insider, among other leading news publications. Regionally, Jessie has received multiple accolades for her leadership, including Seattle Business Magazine’s 2015 Executive Excellence Award in the “CEO of the Year” category, GeekWire’s 2019 “Big Tech CEO of the Year” award, the Puget Sound Business Journal’s 2012 “Women of Influence” and 2020 “Innovator of the Year” awards, and the Ernst & Young 2019 “Entrepreneur Of The Year®” award in the Pacific Northwest region.
Jessie has supported the broader education community by serving on several boards, including Discovery Education, Quizlet, Class.com, and Western Governors University. She is also a board trustee of The Aspen Institute and the Pahara Institute. She has been a featured speaker at many international events, including TEDx Rainier, U.S. News and World Report’s STEM Solutions Conference, SXSWedu, DENT, GeekWire Summit, and the ASU GSV Summit. 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 for the Aspen Institute.
About Owl Ventures
Owl Ventures is the largest venture capital fund in the world focused on the EdTech market with over $2 billion assets under management. The Silicon Valley and London based firm invests in the world’s leading education technology companies across the education spectrum encompassing PreK-12, higher education, future of work (career mobility/professional learning), and “EdTech+” (intersection of EdTech and other major industries such as FinTech and healthcare). Owl Ventures has deep domain expertise and leverages a global network of Limited Partners, investors, and strategic partners to help entrepreneurs scale their businesses into transformative category leading companies. Learn more at www.OwlVC.com. Owl’s annual Education Outcomes Report can be viewed at www.OwlVC.com/outcomes.php.
