The DreamBox Learning Management Team

Jessie Woolley-Wilson

Jessie Woolley-Wilson

Chair, CEO and President

Jessie is president and CEO of DreamBox Learning. Prior to joining DreamBox, Jessie held several executive positions in leading EdTech companies including, Kaplan, LeapFrog SchoolHouse, and Blackboard’s K-12 Group.

Jessie supports the broader K12 industry by serving on the boards of several educational organizations including the International Association for K12 Online Learning (iNACOL), the Woodrow Wilson Foundation, and Islandwood. Jessie 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.

Jessie holds an MBA from Harvard Business School and a BA from the University of Virginia. 

Jennifer Agustin

Jennifer Agustin

Vice President of Marketing

Jen brings more than 15 years of experience as a B2B marketer to DreamBox, most recently growing the Marketing Solutions business at LinkedIn. Prior to LinkedIn, Jen was the senior director of marketing at Bizo, where she helped the company build its content and lead generation functions, managed the social and product marketing teams, and ultimately helped contribute to Bizo’s $50m+ revenue run-rate until the LinkedIn acquisition. She currently leads marketing at DreamBox including PR, demand generation, content marketing, product marketing, and social strategy. Jen holds a BA in English Language and Literature from the University of Chicago.

Mark D Agostino

Mark D’Agostino

Vice President of Product Management

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 User Experience

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 Amazon.com. 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

Controller

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

Senior Vice President of Product Development

Todd Howson brings 15 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

Vice President of Learning

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.

Maris Krieger

Maris Krieger

Director of Human Resources

Maris Krieger brings 15 years of human resources management experience to DreamBox Learning.  She has deep experience in talent acquisition and onboarding, leadership development, performance management, and employee engagement and retention.  Maris also brings expertise in organizational development and cultivating collaboration between HR and functional teams. She has experience at both private and publicly traded organizations and has played pivotal roles in multiple merger processes, organizing growing teams and aligning processes.  Before joining DreamBox, Maris worked as HRBP at ECONET and lead HR functions at Fazer, Nortal, and Swedbank (IT & Product Development division).

James Stoffer, Vice President of Business Development

James Stoffer

Vice President of Business Operations

James brings nearly 15 years of business development, operations, and high revenue growth experience ranging from start-up to mature enterprise technology companies. He was most recently at edtech SaaS company MasteryConnect, where he served as VP of Sales to scale revenue and client success teams from five to over 40 employees. Before MasteryConnect, he spent over 10 years at Hobsons, where he served in many sales and business development leadership roles across K-12 and higher education divisions. James shares in DreamBox’s deep passion for scaling education solutions that transform lives by changing the way people learn. He currently leads business development, sales operations, client success/experience, client support, and professional services at DreamBox. He holds a BS from Clemson University and an MBA from Xavier University.