DreamBox Learning Video

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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 100+ 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
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 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 collegeboard.com, 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


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


Senior Vice President, Client Engagement and 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


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.

DreamBox Learning Reviews

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Jessie Woolley-Wilson
10 Ratings
  • Helpful (1)

    Fast, Furious and Fun Ride

    • Work/Life Balance
    • Culture & Values
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    • Comp & Benefits
    • Senior Management
    Current Employee - Sales
    Current Employee - Sales
    Positive Outlook
    Approves of CEO

    I have been working at DreamBox Learning full-time (More than 3 years)


    I've worked at DreamBox for over 3 years. Like any start up; there has been growing pains; however, if you are the type of person that enjoys change, is open to fulfilling responsibilities "more than your role" when the team is in need; and being a part of an organization that is truly impacting the way kids learn - this is the place! It has been very rewarding to stick with it during the growing pains over the years and see how far the company has come in such a short amount of time. Truly rewarding!


    Due to the rapid growth; unfortunately, onboarding has not been ideal. It's a "chug from the water-hose" crazy amounts of info and go for it... type experience. I'm a firm believer in "learning by doing"; which falls in line with DreamBox's lessons. You have to be willing to dive in and go for it; not be afraid to make mistakes...and learn from them. However, there is room for improvement with a more structured onboarding experience that is more "sticky" and less rushed.

    Advice to Management

    Take a moment to reflect and celebrate how far DreamBox has come in the past few years. Celebrate the small wins with your employees that have led to big outcomes. Given the company is in a high-growth/fast-paced phase, it's easy to get into a cycle of stress that translates to your employees and effects overall morale.

DreamBox Learning Interviews

Interview Experience

Interview Experience


Getting an Interview

Getting an Interview


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Interview Difficulty




    Client Sucess Interview

    Anonymous Employee in Raleigh, NC
    Accepted Offer
    Positive Experience
    Average Interview


    I applied through other source. The process took 2 weeks. I interviewed at DreamBox Learning (Raleigh, NC) in March 2015.


    Very thorough. They are looking for Quality not Quantity. They want to know want to make this a career not a job. Also they look for those type of individuals who are willing to work as a team but also work on your own. Be able to answer the phone and deal with individuals who are stressed.

    Interview Questions

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 51 to 200 Employees
Founded 2006
Type Company - Private
Industry Education
Revenue $5 to $10 million (USD) per year

At DreamBox, we believe all children can excel at learning, no matter where they start, where they live, or who they are. Along with district administrators, teachers, principals, and parents, we are dedicated to helping children realize their potential. Yet every child must be challenged, encouraged, and engaged in an individual way. That’s why we developed our revolutionary Intelligent Adaptive Learning™ technology, and combined it with a rigorous curriculum and an engaging game-like environment, to change the learning paradigm..

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