DreamBox Learning

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DreamBox Learning – Why Work For Us?


DreamBox Learning’s Vision for the Future of Learning

Every student can excel in math, no matter where they start, where they live, or who they are. And every teacher, principal, and parent wants the children in their care to realize this potential. Yet every child must be challenged, encouraged, and engaged in their own way.

At DreamBox Learning, we’ve developed the adaptive learning technology that can change the paradigm of learning, by integrating individualized instruction with continuous embedded assessment, and with a rigorous curriculum presented in an engaging, motivating way. The DreamBox adaptive learning platform is the only product that has the power to deliver millions of different learning paths, each one tailored to a student’s specific learning needs and level of comprehension. The result is an effective, engaging, and highly individualized learning environment for every student.

Core beliefs that guide our vision

  • Children persist in learning when they are engaged, challenged and having fun.
  • Students are teachers as well as learners who can drive their own progress.
  • Teachers need support for differentiating instruction to a broad range of learners.
  • To thrive as life-long learners requires mastery of math concepts and problem-solving skills.

Our future depends on helping the next generation learn how to learn. DreamBox Learning believes that all students can exceed their own and others’ expectations. With the right learning environment, one adapted to each child’s unique skills and needs, we can help millions of students achieve this vision.

DreamBox Learning is looking for you

Think you have something special to share? Want to make a difference in the online learning space? We'd love to hear from you!


DreamBox is on a mission to radically change the way students learn by developing an industry-leading adaptive learning program that combines online gaming technology with a rigorous curriculum designed by nationally board-certified teachers — the best from across the country.

What's the best part? You’ll be blazing the trail toward improving the way kids learn.

We believe we can really make a difference in education. If you do too, come join us!

Grow Your Career

  • We embrace cultural diversity
  • We operate in a fast-paced, energetic, unique and fun environment
  • We've grown to 50+ people – small enough to innovate like a start-up; big enough to operate like a business
  • We vow to support your professional development to help you grow and succeed
  • We provide full health benefits and competitive compensation

DreamBox Learning is proud to offer employees and their families a comprehensive benefits package.  We pay 100% of the monthly employee premium and 50% of the premium for enrolled dependents.


  • Medical
  • Dental
  • Vision


  • Short Term Disability
  • Long Term Disability
  • Life Insurance
  • Accidental Death & Dismemberment


  • 401(k) & Roth 401(k)


  • Health Care
  • Dependent Care
  • Point-of-Service Debit Card for Health Care expenses


  • Paid Time Off
  • Paid Holidays & a Floating Holiday
  • DreamBox Heroes Volunteer Time
  • Bereavement Leave
  • Leaves of Absence


  • Employee Assistance Program
  • Emergency Travel Assistance (Business & Personal)
  • Identity Theft Protection
  • On-Site Parking
  • Transportation Subsidy
  • On-Site Shower Facilities
  • Dogs @ the office

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

Jessie Woolley-Wilson is Chair, President and CEO of DreamBox Learning®, the company that developed the Intelligent Adaptive Learning™ platform 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 and education technology to DreamBox Learning. Throughout her career in the education industry, Jessie has held several leadership roles in general management, sales and marketing, operations, and business development.

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 several boards for nonprofit organizations including the International Association for K-12 Online Learning (iNACOL); Editorial Projects in Education, which publishes Education Week; the Education Innovation Network; Camelot For Kids; the Software & Information Industry Association (SIIA); and Technology Access Foundation (TAF).  Jessie has also served on the World Economic Forum’s Global Agenda Council on Technology and Education.  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 with him 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 then 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 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.

DreamBox Learning Reviews

19 Reviews
19 Reviews
Rating Trends

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Jessie Woolley-Wilson
5 Ratings

    DreamBox is a great place to work

    • Comp & Benefits
    • Work/Life Balance
    • Senior Management
    • Culture & Values
    • Career Opportunities
    Current Employee - Anonymous Employee
    Current Employee - Anonymous Employee

    I have been working at DreamBox Learning


    I am excited to come into work each and everyday. We do great things for children. The people I work with and the service we provide are incredible. The company culture is unmatched. A deep sense of purpose is shared across the organization and the employees.


    None that I can think of.

    Advice to ManagementAdvice

    Keep the bar high and let the product and the mission speak for itself.

    Positive Outlook
    Approves of CEO

DreamBox Learning Awards & Accolades

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Tech Impact Award, Seattle Business Magazine, 2013
Reader's Choice: Top 100 Products, District Administration Magazine, 2013
Return on Education (ROE) Innovation Award, ASU/GSV, 2013
Impact 15, Forbes, 2012
CODiE Award Finalist (Best Mathematics Instructional Solution), SIIA, 2013
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Additional Info

Website www.dreambox.com
Headquarters Bellevue, WA
Size 6 to 15 Employees
Founded 2006
Type Company - Private
Industry Education
Revenue Less than $1 million (USD) per year

At DreamBox Learning, we are dedicated to delivering an effective, engaging learning experience that will enable millions of students to have fun learning math every day.

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