The DreamBox Learning Management Team

Jessie Woolley-Wilson

Jessie Woolley-Wilson

President, CEO, & Chairman of the Board

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 eLearning sector by nationally renowned academic and technology pundits.  Jessie brings nearly two decades of experience in K-12 e-learning to DreamBox Learning. Throughout her career in the education technology industry, Jessie has held several leadership roles in leading education companies.

Before joining DreamBox Learning, Jessie was President of the K–12 Group at Blackboard where she led the company’s growth and development for the virtual and blended online learning market.  Prior to Blackboard, she was President of LeapFrog SchoolHouse, the schools division of LeapFrog Enterprises, where she established SchoolHouse as a leader in education technology and one of the fastest growing educational software producers in the United States. 

Jessie has also held leadership positions at collegeboard.com, the interactive division of the College Board; MyRoad.com, an e-learning company that helps middle school, high school, and college students prepare for college and careers; and Kaplan, the leading test preparation company in the United States.

As an education industry leader, Jessie serves on boards for several organizations including the International Association for K-12 Online Learning (iNACOL); ASU/GSV Education Innovation Summit; Camelot Education; and the Woodrow Wilson Foundation.  Locally, Jessie serves on the boards of Islandwood, an environmental learning center that connects children to the outdoors, and Friends of Waterfront Seattle. Jessie also has 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.  In 2012, she was named to the Forbes “Impact 15″ list for being a disruptor of education and honored as a “Woman of Influence” by The Puget Sound Business Journal for making an impact in the education technology industry as well as the community.  In 2011, Jessie was spotlighted as a “Best Leaders to Watch” in EdNET’s “Best for 2011,” a peer recognition program.

Jessie received her MBA from Harvard Business School and her 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.

Daniel Kerns

Daniel Kerns

Senior Vice President of Product Innovation

Dan has over 20 years of software development experience. Previously, Dan was VP of Engineering for Pure Networks, where he was instrumental in identifying, securing and delivering their flagship AOL business. Dan was also Director of Engineering for VMware, and has consulted for a number of large clients through his firm Sand Point Engineering. He was also an Entrepreneur in Residence at Ignition Partners. Earlier in his career, Dan spent 9 years in a variety of roles at Pure/PureAtria/Rational Software, where he was the Chief Engineer on the Purify product for UNIX and Windows NT platforms and had significant experience managing interactions with strategic partners. Before Pure Software, Dan spent 5 years at Multiflow Computer and Data General Corporation, where he worked on microcode for computers including the DG MV/20000.

Dan earned his Bachelor of Technology in System Software in the School of Computer Science at the Rochester Institute of Technology, his M.S. in Computer Science from the University of Washington, and certificates in management and finance from Stanford University.

Jason Bedford

Jason Bedford

Vice President of Sales and Client Success

Jason directs national sales and training at DreamBox Learning, leading strategic accounts development and managing the company’s eastern regional office in Raleigh, NC. Jason brings over a decade of experience in sales, strategy and operations at leading education technology companies providing software-as-a-service (SaaS) solutions to the K-12 market.

Before joining DreamBox Learning, Jason served as VP Global Sales for Blackboard Connect, a leading learning management system provider. Jason was previously General Manager and EVP at Alert Now, a leading alert notifications solution. With more than five years of experience teaching in Wake County North Carolina Public Schools, Jason has a unique perspective on the value of integrating DreamBox Learning Math in the classroom.

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.