DreamBox Learning Management Team

DreamBox Learning’s team brings an unprecedented combination of experiences. We’re entrepreneurs, educators, creative designers, and technologists. We’ve built successful companies from the ground up, developed world-class software products, taught in the classroom, published research on education, and produced award-winning children’s entertainment products and services. We’re also passionate about providing all children with the very best educational opportunities!

Jessie Woolley-Wilson
President, CEO, & Chairman of the Board

Jessie brings nearly two decades of experience in K-12 eLearning and education technology to DreamBox Learning. Throughout her career in the education industry, Jessie has held several leadership roles in general management, sales & marketing, operations and business development. Most recently, Jessie served as President of K12 & K-20 Strategy at Blackboard where she led Blackboard’s growth and development strategy for the K12 group. Prior to joining Blackboard, she served as President of LeapFrog SchoolHouse, the schools division of LeapFrog Enterprises, where she was instrumental in establishing SchoolHouse as a leader in education technology and one of the fastest growing educational software producers in the U.S.

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

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 and serves on several boards of non-profit organizations, including the National Education Association Foundation, the Partnership for 21st Century Skills, the Ron Brown Scholars Program, and Editorial Projects in Education Inc. (EPE), which publishes Education Week. She was named as one of five “Leaders to Watch” in EdNET’s Best for 2011, a peer recognition program. Jessie has also served on the World Economic Forum’s Global Agenda Council on Technology and Education, an independent international organization committed to improving the state of the world by engaging leaders in partnerships to shape global, regional and industry agendas.

Daniel Kerns
Vice President, Chief Architect

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.

Greg Long
Senior Vice President of Product Development

Mr. Long leads DreamBox Learning’s curriculum, software development, and engagement teams. He is a 15-year veteran of the education technology industry and has played an integral role in helping grow companies by building high performance development teams in areas including content, software development, quality assurance, product and program management. Previously, Greg served as Chief Product Officer for Rosetta Stone, spearheading product development and creating highly personalized interactive tools that unlock the natural language-learning ability in everyone; and most recently as Senior Vice President of Corporate Development, where he was instrumental in growing the company from $90 million to more than $250 million before it went public in 2009.

Prior to Rosetta Stone, Mr. Long was Senior Vice President of Product Development at LeapFrog SchoolHouse, where he led the engineering and content groups for the K-8 schools division. He partnered with Woolley-Wilson at LeapFrog for over three years and was part of the team that grew the company from a $12 to $80 million company in three years. Greg was also Vice President of Content Development at The Learning Company (a Mattel Company).

Greg holds a BA in economics from the University of Victoria, British Columbia, and an MBA from Queen’s University, Kingston, in Ontario, Canada.

Sherri Bealkowski
Vice President of Sales and Client Care

A technology executive with deep education experience, Sherri began her 30-year career at IBM in product development, enterprise sales, and regional channel development. During her 10-year tenure at Microsoft, she was responsible for the US Education Sales and Services and worldwide education strategy, growing the business to over $1b worldwide. She launched the Microsoft Partners in Learning program, a $250m investment in emerging markets and low-income schools, which increases access to technology in schools and empowers teachers to use it effectively in over 100 countries. Before joining DreamBox, Sherri was an educational technology consultant and served as Interim CIO at Seattle Public Schools and as Chief Operating Officer for an education software startup in Redmond, WA.

Sherri holds a Bachelor of Mechanical Engineering degree from the Georgia Institute of Technology, and a Master of Business Administration and a Master of Computer Science from Florida Atlantic University. She was inducted into the Georgia Tech Academy of Distinguished Engineering Alumni in 2003 and has a long history of professional and civic participation including the Society of Women Engineers, Big Brothers/Big Sisters, and many programs that empower middle and high school girls to excel in math, science and technology.

Patti Smith
Vice President of Marketing and Product Management

With 20 years experience marketing educational solutions in the K-16 market, Patti has devoted the past 9 years to developing and promoting products for K-12 institutional sales with particular emphasis on mathematics programs. As Vice President of K-12 Mathematics Portfolio at Houghton Mifflin Harcourt she was responsible for driving product strategy to improve financial performance including capital investment, product concept development, pricing and promotion throughout the product life cycle. For the past year she has been devoted to understanding current and future implications of the Common Core State Standards on classrooms and to developing a strategic response to this initiative.

As Director of Marketing at Thinkwell, a multimedia publisher, Patti spearheaded promotional efforts that led to growth from initial product launch to use in over 350 colleges and universities within 18 months.

Patti received her MBA from The University of Texas at Austin, her BA in English from The University of Virginia, and her BS in Education from Virginia Commonwealth University.

Anne Richard
Controller

Anne brings over 13 years of experience in finance and accounting at high-growth companies. Most recently Anne worked as controller for Naverus, Inc., where she played a key role in their successful acquisition by GE Aviation. Previously she held the role of controller for A Place for Mom and ShareBuilder Corporation, where she developed accounting systems and controls for these very early stage companies. She has deep experience in financial management and reporting as well as annual budget planning, revenue forecasting and due diligence associated with M&A activities. Additionally, Anne has enhanced internal education around finance and operations.

Anne earned an MBA from Seattle University and holds a CPA License in Washington State.