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DreamBox Learning Overview

Bellevue, WA
51 to 200 employees
Company - Private
Education Training Services
Unknown / Non-Applicable
For 10 years, DreamBox Learning ® has re-imagined how students learn math. We provide an experience that inspires students to seek the struggle that leads to learning, and to feel the courage and the confidence that comes from genuine understanding. We ... Read more

Company Updates

  • DreamBox Learning CEO Jessie Woolley-Wilson was named 1 of 8 Unstoppable Eastside Women by 425 Magazine. She says DreamBox is about more than math lessons; it’s about getting students to believe in themselves as they learn.

    Unstoppable Eastside Women - 425 Magazine

    Imagine what kind of world it would be if everyone took a look around and identified something they could improve, contribute to, or create. And then they did. We met eight women with strong Eastside roots who are working to make things better here at home, and around the world.

  • Join us for our webinar December 8th. Leland Kriegh, Professional Development Specialist, will share resources to help you develop your students’ math mindset and how you can foster this in & outside the classroom.

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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, 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.


Vice President of Marketing

Jen brings more than 15 years of experience as a B2B  marketer  to DreamBox, most recently growing the  Marketing Solutions  business at LinkedIn. Prior to  LinkedIn, Jen was the senior  director of marketing at  Bizo, where she helped the company  build its content  and lead generation functions, managed the  social and  product marketing teams, and ultimately helped  contribute to Bizo’s $50m+ revenue run-rate until the  LinkedIn  acquisition. She currently leads marketing at DreamBox  including PR, demand generation, content marketing, product  marketing, and social strategy.

Jen holds a BA in English Language and Literature from the University of Chicago.


Senior Vice President of Technology

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.


Vice President of Finance & Operations

Kelly Havens brings over 10 years of experience in the  accounting profession. She started her career in public  accounting, serving clients of various sizes and  industries in the  Audit & Attestation practice. She has  spent the rest of her  career in Seattle’s gaming and tech  industries. Kelly has a BA in  Accounting from Seattle  Pacific University and holds her CPA  license in the State  of Washington. Kelly heads up the  Accounting and  Finance team at DreamBox. With two young  kids at home, she is deeply passionate about both children and  their education.


Senior 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.


Vice President of Personalization

Nigel Green has extensive experience as both a teacher  and  software developer. Prior to moving to the United  States in  1991 from his native Australia, Green was a K–  8 educator and  faculty member at the University of  Melbourne. He has since  worked at several startups, including spending eight years at Green has designed many award-winning  products and is the sole or joint inventor of more than 20  patents, and is responsible for much of DreamBox Learning’s  effective Intelligent Adaptive technology. Green currently  oversees many areas at DreamBox that contribute to the user experience, from the Intelligent Adaptive engine to how lessons are designed and written to data mining. He is a graduate of the University of Melbourne.



Vice President of Products & Services

Mark D’Agostino has more than 20 years of experience  helping  organizations use data analysis and technology  to solve  complex problems and improve their  effectiveness. Before  joining DreamBox, D’Agostino was  the Senior Vice President of  Product Management at  Applied Predictive Technologies. At APT  he guided the  development of innovative, software-as-a-service  products that are used by more than 100 of the largest  companies in the world to measure their impact and improve  their effectiveness. In previous roles at Accenture China, Dean &  Company, and Mercer Management Consulting, he consulted with leading companies in retail, consumer products, telecommunications, and other industries to identify and realize business improvement opportunities. D’Agostino is passionate about improving educational opportunities for all children and is a founder of the Grassroots Education Project, which has provided over 20,000 hours of volunteer service to students in Washington, D.C. He has a degree in Physics and Electrical Engineering from the Massachusetts Institute of Technology.


Senior Director of Employee Experience

Maris Krieger brings 15 years of human resources  management  experience to DreamBox Learning.  She  has deep experience in  talent acquisition and  onboarding, leadership development,  performance  management, and employee engagement and  retention.  Maris also brings expertise in organizational  development and cultivating collaboration between HR  and  functional teams. She has experience at both  private and  publicly traded organizations and has played pivotal roles in  multiple merger processes, organizing growing teams and  aligning processes.  Before joining DreamBox, Maris worked as  HRBP at ECONET and lead HR functions at Fazer, Nortal, and Swedbank (IT & Product Development division).


Vice President of Sales

James brings nearly 15 years of business development, operations, and high revenue growth experience ranging from start-up to mature enterprise technology companies. He was most recently at edtech SaaS company MasteryConnect, where hJames Stoffer, Vice President of Business Developmente served as VP of Sales to scale revenue and client succe
ss teams from five to over 40 employees. Before MasteryConnect, he spent over 10 years at Hobsons, where he served in many sales and business development leadership roles across K-12 and higher education divisions. James shares in DreamBox’s deep passion for scaling education solutions that transform lives by changing the way people learn. He currently leads sales at DreamBox. He holds a BS from Clemson University and an MBA from Xavier University.

DreamBox Learning Reviews

Rating TrendsRating Trends
Recommend to a friend
Approve of CEO
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Jessie Woolley-Wilson
36 Ratings
  • Featured Review

    Helpful (2)

    "Awesome mission, great team and challenging"

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Former Employee - Anonymous Employee in Bellevue, WA
    Former Employee - Anonymous Employee in Bellevue, WA
    Positive Outlook
    Approves of CEO

    I worked at DreamBox Learning full-time (More than 3 years)


    DreamBox in many ways was a pinnacle experience for me. No team is perfect, but when everyone lives/works with clear vision and strives to live out values, anyone can contribute, fail/learn, grow professionally and personally. You can fail here if learning comes quickly and you own your contribution.


    The EdTech marketplace is tough; having such a great product, marketplace progress can seem slow and is certainly political. The 'but' here is DreamBox leadership is indefatigable when it comes to making a difference and continuing its progress.

    Advice to Management

    don't waiver from the great culture you have. Never give up on the kids and making DreamBox a game changer.

See All 61 Reviews

DreamBox Learning Photos

DreamBox Learning photo of: Bring your kids to work day 2015
DreamBox Learning photo of: Tina, Content Architect
DreamBox Learning photo of: Tina, Content Architect, and the Gub!
DreamBox Learning photo of: Tina, Content Architect, and the Gub!
DreamBox Learning photo of: Zina, Jen, Mike, Maureen, and Maris at #SFS2017 for Bellevue Schools Foundation.
DreamBox Learning photo of: Our Bellevue Team at the Annual Picnic!
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DreamBox Learning Interviews



Getting an Interview

Getting an Interview




  1. Featured Interview

    Helpful (2)  

    Principal Software Engineer Interview

    Anonymous Employee in Bellevue, WA
    Accepted Offer
    Positive Experience
    Average Interview


    The process took 3 weeks. I interviewed at DreamBox Learning (Bellevue, WA) in April 2016.


    I was contacted by a friendly, knowledgable recruiter. They invited me in for a face-to-face interview, and the manager who interviewed me was passionate about the team, product, and was extremely technically competent. There were a couple light technical white-board questions, and a take-home coding question that was somewhat meaty and just a ton of fun. They then invited me in for more on-site technical interviews, which probed into my solution for the take home coding question, as well as more white-board coding. Overall, pretty standard technical interview loop stuff. The people I met with were all extremely technically competent, and very easy to connect with and talk to. Simply fantastic group of people, honestly. I was really impressed with how quickly and efficiently the process was run. Front to back, the whole thing was less than 3 weeks, and I had an offer the morning after my on-site interview. And this was over spring break with some key people out. They take hiring very seriously at DreamBox.

    Interview Questions

    • Standard coding questions, data structures, algorithms.   1 Answer
See All 7 Interviews

DreamBox Learning Awards & Accolades

  • Return on Education (ROE) Innovation Award, ASU and GSV, 2015
  • Best PK-12 Personalized Learning Solution, Software & Information Industry Association (SIIA), 2015
  • Growth50, Tyton, 2015
  • Award of Excellence, Tech & Learning Magazine, 2014
  • Tech Impact Award, Seattle Business Magazine, 2013
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Work at DreamBox Learning? Share Your Experiences

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