The DreamBox Learning Management Team

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. Today, DreamBox serves nearly 3 million K-8 students and approximately 120,000 teachers. The company provided more than 350 million math lessons across the U.S. and Canada in 2017.

Jessie recently secured a $130 million investment in DreamBox from The Rise Fund, a global impact investing fund managed by TPG Growth. Prior to joining DreamBox, Jessie served as president of Blackboard’s K-12 Group and 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, the Western Governors University Board of Trustees, and Ursuline Academy. She is also a board member for Boeing Employees Credit Union, Pacific Science Center, and The Bullitt Foundation. She has been a featured speaker at international events including TEDx Rainier, SXSWedu, DENT and GeekWire Summit 2018.

Jessie is a two-time recipient of EdTech Digest’s EdTech Leadership Award for her work in transformative innovation in education and honored her as one of 2018’s Top 100 Influencers in EdTech. 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.

Mark D Agostino

Mark D’Agostino

Vice President of Product and Services

Mark D’Agostino has more than 20 years of experience helping organizations use data analysis and technology to solve complex problems and improve their effectiveness. Before joining DreamBox, D’Agostino was the Senior Vice President of Product Management at Applied Predictive Technologies. At APT he guided the development of innovative, software-as-a-service products that are used by more than 100 of the largest companies in the world to measure their impact and improve their effectiveness. In previous roles at Accenture China, Dean & Company, and Mercer Management Consulting, he consulted with leading companies in retail, consumer products, telecommunications, and other industries to identify and realize business improvement opportunities. D’Agostino is passionate about improving educational opportunities for all children and is a founder of the Grassroots Education Project, which has provided over 20,000 hours of volunteer service to students in Washington, D.C. He has a degree in Physics and Electrical Engineering from the Massachusetts Institute of Technology.

Nigel Green

Nigel Green

Vice President of Personalization

Nigel Green has extensive experience as both a teacher and software developer. Prior to moving to the United States in 1991 from his native Australia, Green was a K–8 educator and faculty member at the University of Melbourne. He has since worked at several startups, including spending eight years at Green has designed many award-winning products and is the sole or joint inventor of more than 20 patents, and is responsible for much of DreamBox Learning’s effective Intelligent Adaptive technology. Green currently oversees many areas at DreamBox that contribute to the user experience, from the Intelligent Adaptive engine to how lessons are designed and written to data mining. He is a graduate of the University of Melbourne.

Kelly Havens

Kelly Havens

Vice President of Finance and Operations

Kelly Havens brings over 10 years of experience in the accounting profession. She started her career in public accounting, serving clients of various sizes and industries in the Audit & Attestation practice. She has spent the rest of her career in Seattle’s gaming and tech industries. Kelly has a BA in Accounting from Seattle Pacific University and holds her CPA license in the State of Washington. Kelly heads up the Accounting and Finance team at DreamBox. With two young kids at home, she is deeply passionate about both children and their education.

Todd Howson

Todd Howson

Chief Technology Officer

Todd Howson brings 20 years of software development experience ranging from startups to large-scale enterprise systems. He was previously Director of Engineering at Amdocs Interactive, where he ran a global software development organization building high-scale mobile transaction processing, content management, content discovery, content delivery, and reporting products for customers, including AT&T, Verizon, Sprint, T-Mobile, and American Movil. Prior to that position, he held various technical and managerial positions for Qpass, a mobile commerce startup that was acquired by Amdocs. Howson holds a BA from Washington State University with an emphasis in information systems and computer science.

Tim Hudson

Dr. Tim Hudson

Chief Learning Officer

Dr. Tim Hudson is a learning innovator and education leader who frequently writes and speaks about the intersection of learning, schooling, and technology. At DreamBox, Dr. Hudson oversees the development of innovative learning experiences that engage students in mathematical thinking and provide teachers with useful information to support differentiation and personalization in their classrooms. He has spoken at national conferences such as ASCD, iNACOL, NCTM, and SXSWedu and along with DreamBox advisor Cathy Fosnot, co-authored the chapter “Classrooms Where Children Learn” in an NCTM book about Mathematics Intervention. Prior to joining DreamBox, Dr. Hudson spent more than 10 years working in public education, first as a High School Mathematics Teacher and then as a K–12 Mathematics Coordinator and Strategic Planning Facilitator for the Parkway School District in suburban St. Louis, MO. Follow his conversations on Twitter (@DocHudsonMath) and on the DreamBox Learning blog.

James Stoffer, Vice President of Business Development

James Stoffer

Senior Vice President of Sales and Client Experience

James brings nearly 15 years of business development, operations, and high revenue growth experience ranging from start-up to mature enterprise technology companies. Prior to DreamBox, James spent over 10 years at Hobsons in sales and business development leadership roles across K-12 and higher education divisions, and most recently scaled revenue and client success teams as VP of Sales at edtech Saas company MasteryConnect. Demonstrating DreamBox’s deep passion to change the way the world learns, James currently leads the new, expansion, client experience, and renewal businesses at DreamBox. He holds a BS from Clemson University and an MBA from Xavier University.