The DreamBox Learning Management Team

Jessie Woolley-Wilson

President and CEO

Jessie Woolley-Wilson is driven by a singular belief that all children deserve high-quality learning opportunities, regardless of who they are or where they live. For more than 20 years, Jessie has worked in the education technology space to support school and district leaders in improving learning and life outcomes for K-12 students.

Jessie joined DreamBox Learning® in 2010 as Chair, President, and CEO. 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. The company’s pioneering Intelligent Adaptive Learning™ platform has won more than 40 top education and technology industry awards and is used by 200,000 teachers and nearly 5 million students in all 50 states and throughout Canada and Mexico.

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 held leadership positions at, 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 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. 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 supports the broader education community by serving on several boards, including Rosetta Stone and the Western Governors University Board of Trustees. 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 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.

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.

Jamie Gier

Jamie Gier

Senior Vice President of Marketing

Jamie’s career encompasses more than two decades in marketing leadership roles with privately-held and publicly traded healthcare technology companies ranging in size from start-ups to Fortune 500. Prior to joining DreamBox, Jamie held executive-level positions at SCI Solutions, Microsoft, GE Healthcare, and IDX Systems Corporation. She has been involved in a number of industry mergers and acquisitions.

For three years, Jamie served as a board member for Page Ahead, a nonprofit focused on the literacy needs of at-risk kids in Washington state, and chaired its marketing and fund development committee. She graduated summa cum laude from Washington State University with a bachelor’s degree in Communications.

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.

James Stoffer, Vice President of Business Development

James Stoffer

Senior Vice President of Sales

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, and renewal businesses at DreamBox. He holds a BS from Clemson University and an MBA from Xavier University.

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.