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The DreamBox Learning Management Team

Jessie Woolley-Wilson

President and CEO

Jessie Woolley-Wilson is President and CEO of DreamBox Learning®. Prior to joining DreamBox, Jessie held executive positions at multiple leading EdTech companies, including Blackboard, LeapFrog, and Kaplan.

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 a “Top 100 Influencers in EdTech.” Forbes placed her on its “Impact 15” list for being a disruptor in education, and The New York Times featured Jessie in its Corner Office column.

Regionally, Jessie has received many accolades, including Seattle Business Magazine’s Executive Excellence Award in the “CEO of the Year” category, GeekWire’s “Big Tech CEO of the Year” award, Puget Sound Business Journal’s “Women of Influence” and “Innovator of the Year” awards, and the Ernst & Young “Entrepreneur Of The Year®” award in the Pacific Northwest region.

She has served on several boards, including Rosetta Stone and the Western Governors University Board of Trustees. She has been a featured speaker at many events, including TEDx Rainier, 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.

Nigel Green

Nigel Green

Senior Vice President of Personalization and Learning Innovation

Nigel’s experience encompasses a career in both education and software development. 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 later worked at several technology startups, along with spending eight years at Amazon. Throughout his career, Nigel has designed several award-winning products and is the sole or joint inventor of more than 20 patents. Among these many accomplishments, Nigel was instrumental in developing DreamBox Learning’s Intelligent Adaptive Technology platform, which provides kids with a personalized math learning experience. Today, Nigel remains closely involved in driving enhancements to the Intelligent Adaptive engine and the user experience for students, educators and learning guardians. He is a graduate of the University of Melbourne.

Todd Howson

Todd Howson

Chief Technology Officer

Todd Howson brings 20 years of software development experience ranging from startups to large-scale enterprise systems. Prior to joining DreamBox, Todd held the role of 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.

Lance Ludman

Lance Ludman

Chief Financial Officer

Before joining DreamBox Learning, Lance spent almost nine years with Blackbaud (NASDAQ: BLKB), most recently as the CFO for its Enterprise Markets Group. He also served as the CFO for Blackbaud’s International Markets Group for three years and as Corporate Development Director for three years. Blackbaud is the largest pureplay software provider to the nonprofit market.

Lance joined Blackbaud after five years in corporate and business development with Savi Technology, a venture capital-backed logistics software company acquired by Lockheed Martin in 2006.

Lance received his B.A. in International Affairs from the University of Richmond and his M.A. in International Economics from the George Washington University. He has numerous nonprofit interests, and serves as the Treasurer of the Lowcountry Children’s Museum in Charleston, SC.

Dianna Winegarden, Senior Vice President of Client Success

Dianna Winegarden

Senior Vice President of Client Success

Dianna is a proven leader of global Client Services organizations, bringing experience from a range of high-growth technology startups to global enterprise companies. Prior to Dreambox, Dianna served as COO for Level Technologies, a Techstars company with a mission to redefine financial services for the gig economy. Dianna and her family previously lived in London, where she was the Global Client Services and Solutions leader for Investis (now Investis Digital).

As Senior Vice President of Client Success, Dianna leads the Client Support, Client Experience and Professional Development teams at Dreambox that deliver a wide range of services to delight our clients.

Dianna holds a BA in International Relations from Drake University, and an MBA from University of Washington. Dianna is active in the Seattle community, serving as a board member for Ventures and a volunteer for Farestart.