The DreamBox Learning Board of Directors

Jessie Woolley-Wilson

Jessie Woolley-Wilson

Chair, CEO and President

Throughout her life and career, Jessie Woolley-Wilson has been driven by a singular belief that all children need and deserve high-quality learning opportunities, regardless of who they are or where they live. She believes that by supporting great teaching and learning, everyone wins: kids, families, communities and the world. Jessie has worked in the education technology space for nearly 20 years to support school and district leaders to improve learning and life outcomes for
K-12 students.

Jessie joined DreamBox Learning® in 2010 as Chair, President and CEO. The startup software company had pioneered Intelligent Adaptive Learning™ in 2006 and began partnering with schools soon after Jessie joined. DreamBox currently serves nearly 2.2 million K-8 students, approximately 80,000 teachers and provided over 255 million math lessons in the 2015-2016 school year across the U.S. and Canada.  Prior to joining DreamBox, Jessie served as president of Blackboard’s K-12 Group and president of LeapFrog SchoolHouse, the K-12 division of LeapFrog Enterprises. Jessie also served in leadership positions at, the interactive division of the College Board, and at Kaplan, the leading test preparation company in the U.S.

Jessie supports the broader K12 industry by serving on the boards of several educational organizations including Rosetta Stone, Newsela, International Association for K12 Online Learning (iNACOL), the Woodrow Wilson Foundation, Western Governors University Board of Trustees and Islandwood. She is also a board member for Boeing Employees Credit Union. She has been a featured speaker at international events including TEDx Rainier, SXSWedu, and DENT.

Jessie is a two-time recipient of EdTech Digest’s EdTech Leadership Award for her work in transformative innovation in education. Seattle Business Magazine awarded Jessie the 2015 Executive Excellence Award in the CEO of the Year category and Forbes placed her on its “Impact 15” list for being a disruptor in education. The Puget Sound Business Journal honored Jessie as a “Woman of Influence” and 425 Magazine named her as one of eight “Unstoppable Eastside Women” for having a clear focus on the greater good. Additionally, The New York Times has profiled Jessie and her leadership style in their Corner Office column.

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.

Reed Hastings

Reed Hastings

Co-founder, Chairman and CEO of Netflix

Reed co-founded Netflix in 1997 and led the successful growth of the company to over 10 million subscribers. Reed is an active educational philanthropist and board member of many non-profits. He was President of the California State Board of Education from 2000 to 2004. He has led successful statewide political campaigns for more charter public schools and easier passage of local school bonds. In addition, Reed is a founding member of, Aspire Public Schools, Pacific Collegiate School, and

In March 2010, Barron’s included Reed among its 30 most respected CEOs of the year. Reed is also on the board of directors of Microsoft and Facebook. Earlier in his career, Reed founded Pure Software, which he built into one of the world’s 50 largest public software companies.
Reed received a BA from Bowdoin College in 1983 and an MSCS degree from Stanford University in 1988. He holds several patents. Between Bowdoin and Stanford, Reed served in the U.S. Peace Corps as a high school math teacher in Swaziland.

Kevil Hall

Kevin Hall

CEO and President, Charter School Growth Fund

Kevin has been CEO and President of Charter School Growth Fund since 2009. Previously, he served as Chief Operating Officer of the Broad Foundation. Kevin is also a co-founder and former senior vice president of business development of Chancellor Beacon Academies, which manages public charter and private schools across the United States.

Earlier in his career, Kevin served as senior vice president of infoUSA, a publicly traded information services company, as well as held positions at McKinsey & Co., Goldman, Sachs & Co., and Teach for America. He has served as an elementary school teacher and as a teaching fellow at Harvard University.

Kevin received a bachelor’s degree with honors in political science and economics from Swarthmore College and an M.B.A. from Harvard Business School.

Paul Holland

Paul Holland

General Partner, Foundation Capital

Paul Holland joined Foundation Capital in 2002. Before joining Foundation Capital, Paul was Senior Vice President of Worldwide Sales at Kana Communications, a leading supplier of Enterprise Relationship Management solutions to strategic e-businesses. Paul built a team of over 350 people that secured more than 900 customers worldwide, helping Kana become one of the top ten IPOs of 1999.

Before Kana, Paul was a Vice President and General Manager for another highly successful start-up, Pure Software, helping raise its market value from $2 million to over $1 billion in his five-year tenure there. Pure had the second most successful IPO of 1995 and was later acquired by Rational Software. Paul began his professional career at SRI International (formerly the Stanford Research Institute).

Paul currently serves on the board of directors for Averail, CalStar Products, Coverity, Inside View, and Serious Energy; is a board observer for Chegg and MobileIron; and was previously on the board of directors for Talking Blocks (acquired by Hewlett-Packard), RouteScience (acquired by Avaya), TuVox (acquired by West) and Ketera (acquired by Rearden Commerce). Paul is also the former President of the board of the Western Association of Venture Capitalists.
Paul received a BS from James Madison University, an MA in Foreign Affairs from the University of Virginia; and an MBA from the University of California at Berkeley. Paul was the originator and co-executive producer of the highly acclaimed documentary on early days of the Silicon Valley called, “Something Ventured”.

Tory Patterson

Tory Patterson

Co-Founder and Partner, Owl Ventures

Tory Patterson is the Managing Partner of Owl Ventures. Tory is actively involved and serves on the board of directors of Newsela, MasteryConnect, PresenceLearning, EdSurge and LearnZillion.

Prior to founding Owl Ventures, Tory was a Partner at Catamount Ventures, a San Francisco based venture capital fund focused on mission-driven companies. While at Catamount, Tory advised several start-ups from the idea stage through launch, financing and commercialization. Tory was a key member of the team that incubated, supported and built Plum Organics, from early vision to becoming the world’s largest organic baby and kids’ food company, to eventual successful exit to Campbell’s. Tory founded and ran Catamount’s education investment practice where he led investments in leading education companies MasteryConnect, PresenceLearning, EdSurge, TenMarks (acquired by Amazon) Upworthy and Declara.

Tory earned a BA from Williams College and an MBA from Stanford’s Graduate School of Business.