Working at DreamBox Learning | Glassdoor

DreamBox Learning Overview

Bellevue, WA
201 to 500 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

  • "It's imperative that we equip our teachers with the skills and resources they need to be successful, so we can slow down attrition, improve retention, and increase teacher effectiveness." @eschoolnews #teachers

    Taking on teacher attrition

    We once believed that teacher effectiveness dramatically increased for the first three to five years on the job and then plateaued. But recent research suggests that substantial growth in effective...

  • How do you make sense of it all? Learn how to use the #dreambox classroom overview report to personalize instruction and close gaps.

    Using Student Proficiency Data to Personalize Instruction and Close Gaps

    If you're new to DreamBox and haven't explored the Classroom Overview report yet, now is the perfect time-especially since you're probably in the throes of preparing your students for your mandated state assessments. The Classroom Overview report will make it easier for you to identify which students are on track and which would benefit from your intervention to help get everyone on track and assessment ready.

See AllSee All

DreamBox Learning Video

Provided by employer [?]


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.


Senior Vice President of Marketing

Jamie’s career encompasses more than two decades in marketing leadership roles with privately-held and publicly traded healthcare technology companies ranging in size from start-ups to Fortune 500. Prior to joining DreamBox, Jamie held executive-level positions at SCI Solutions, Microsoft, GE Healthcare, and IDX Systems Corporation. She has been involved in a number of industry mergers and acquisitions.

For three years, Jamie served as a board member for Page Ahead, a nonprofit focused on the literacy needs of at-risk kids in Washington state, and chaired its marketing and fund development committee. She graduated summa cum laude from Washington State University with a bachelor’s degree in Communications.


Chief Financial Officer

Before joining DreamBox Learning, Lance spent almost nine years with Blackbaud (NASDAQ: BLKB), most recently as the CFO for its Enterprise Markets Group. He also served as the CFO for Blackbaud’s International Markets Group for three years and as Corporate Development Director for three years. Blackbaud is the largest pureplay software provider to the nonprofit market.

Lance joined Blackbaud after five years in corporate and business development with Savi Technology, a venture capital-backed logistics software company acquired by Lockheed Martin in 2006. 

Lance received his B.A. in International Affairs from the University of Richmond and his M.A. in International Economics from the George Washington University. He has numerous nonprofit interests and serves as the Treasurer of the Lowcountry Children’s Museum in Charleston, SC.


Chief Technology Officer

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 & Business 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.


Chief Learning Officer

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.


Senior 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 educators 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.


Senior 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 Vice President of Sales

James Stoffer, Vice President of Business Development

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 he served as VP of Sales to scale revenue and client success 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.


Senior Vice President of Client Experience & Success

Meghan Browne is SVP of Client Experience & Success at DreamBox, where she oversees client onboarding, activation, support, and expansion.  Prior to joining DreamBox, Meghan served as COO at NewSchools Venture Fund, where she led strategy development, communications, operations, HR, and finance. Meghan previously managed the K12 Next Generation Learning portfolio at the Gates Foundation, where she coordinated the investment strategy for $75 million in annual grantmaking and led several complex investment initiatives. Earlier in her career, Meghan was a management consultant and product manager with Point B, Charles Schwab & Co, Razorfish, and MarketBridge, leading strategy development, product development, partner engagement, and technology implementation in the high tech, financial services, healthcare, and retail industries.

DreamBox Learning Reviews

Rating TrendsRating Trends
Recommend to a friend
Approve of CEO
(no image)
Jessie Woolley-Wilson
43 Ratings
  • Featured Review

    "An amazing company culture and inspirational leadership"

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

    I have been working at DreamBox Learning full-time


    DreamBox is a special place to work. People that work here are smart, motivated by a higher purpose and dedicated to the company mission and values. The technologies we work with are modern and super-interesting, and the culture is very low-ego and collaborative. The work is fulfilling at many levels and makes me want to go to work and give my best every day. Leadership is focused on bringing high value to the kids and customers that we serve, and to the employees who do the work to make it happen. Decisions reflect that focus from the ground up.


    The company is growing and evolving. People who can't evolve with the company can misinterpret changes as a lack of organization.

    Advice to Management

    Well done! Keep on pushing!

See All 71 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!
See All PhotosSee All

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 9 Interviews

DreamBox Learning Awards & Accolades

  • 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
See More

Work at DreamBox Learning? Share Your Experiences

DreamBox Learning
  • Star
  • Star
  • Star
  • Star
  • Star
Click to Rate