The DreamBox Learning Management Team

Jessie Woolley-Wilson

Jessie Woolley-Wilson

President, CEO, and Board Chair

Jessie Woolley-Wilson is Chair, President, and CEO of DreamBox Learning®, Inc., the company that pioneered Intelligent Adaptive Learning™—heralded as a “game changer” in the ed-tech sector by nationally renowned academic and technology experts. Jessie has nearly two decades of experience in K–12 e-learning and has held several leadership roles in prominent education companies.

Before joining DreamBox Learning, Jessie was President of Blackboard’s K–12 Group where she led the company’s growth for the virtual and blended online learning market. Prior to Blackboard, she was President of LeapFrog SchoolHouse where she established SchoolHouse as a leader in ed-tech and one of the fastest growing educational software producers in the U.S.; Jessie also held leadership positions at, the interactive division of the College Board, and at Kaplan, the leading test preparation company in the U.S.

As an ed-tech industry leader, Jessie serves on the boards of several educational organizations including the International Association for K–12 Online Learning (iNACOL), Camelot Education, and the Woodrow Wilson Foundation. Locally, she serves on the boards of IslandWood, an environmental learning center that connects children to the outdoors, and Seattle Venture Partners International. Jessie has also served as a member of the World Economic Forum’s Global Agenda Council on Technology and Education, and has presented at TEDx Rainier, SXSWedu, and DENT. She was awarded the 2015 Executive Excellence Award in the CEO of the Year category by Seattle Business magazine; she was also on the Forbes “Impact 15” list for being a disruptor of education, and was honored as a “Woman of Influence” by Puget Sound Business Journal for making an impact in the ed-tech industry.

Jessie has an MBA from Harvard Business School and a BA in English from the University of Virginia. She is a 2007 Henry Crown Fellow of the Aspen Institute.

Peter Biere

Peter Biere

Chief Financial Officer

Peter comes to DreamBox from Gottschalk Hardesty where he was a leader in optimizing financial structures, corporate development and strategy and creating sustainability in start-ups.

Peter is an operationally focused senior financial executive with a 30 year track record building value in middle market, emerging growth and early formation companies in both private and public ownership structures, including 8 years as CFO of two NASDAQ traded companies. Peter’s industry expertise includes retail-direct, high technology R&D and services, software, natural resources, financial services and food manufacturing, with experience spanning a range of business life-cycles from start-up to transition to high-growth to turn-around. Peter’s leadership experience includes business formation, cash management, multiple-stage capital funding, business support systems, teambuilding, exit strategies including IPO and M&A, SEC reporting, SOX implementation and compliance as well as performing interim CEO, COO and general management assignments.
Peter holds a BBA and MA in Accounting from the University of Iowa, and is a CPA.

Jason Bedford

Jason Bedford

Senior Vice President, Client Engagement and Success

A leader in sales, strategy and operations in education technology for more than a decade, Jason brings vast experience and expertise providing software-as-a-service (SaaS) solutions to the K-12 market. He directs client partnerships and leads the sales, marketing, professional services and support teams at DreamBox Learning while managing the company’s eastern regional office in Raleigh, NC. As a former teacher in urban and suburban public schools, Jason offers a unique perspective on the value of integrating DreamBox Learning Math in the classroom and supporting educators with instructional quality transformation.

Before joining DreamBox Learning, Jason served as VP Global Sales for Blackboard, a prominent learning management system provider. He was previously General Manager and EVP at Alert Now, a leading alert notifications solution.

Todd Howson

Todd Howson

Vice President of Engineering

Todd brings 15 years of software development experience ranging from start-ups 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 start-up that was acquired by Amdocs.

Todd holds a BA from Washington State University with an emphasis in information systems and computer science.

Dr Gregory Firn

Dr. Gregory Firn

Superintendent in Residence

Prior to joining DreamBox Learning, Dr. Gregory Firn served as Superintendent, Deputy Superintendent, and in several other educational leadership roles in Texas, North Carolina, Connecticut, Washington state, Nevada, and overseas. Grounded in the school effects research, Dr. Firn’s leadership resulted in school system improvement as measured by student achievement and performance results, increased parent, community, and school engagement, increased graduation rates and decreased student suspensions. A pioneer in digital conversion, he twice led system-wide digital transformation initiatives, including the design and implementation of robust human capital development programs. Dr. Firn earned his doctorate from Seattle Pacific University, where his research focused on learner-centered education.

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.