Trending: ‘Canary in a coal mine’: Seattle marketing tech startup Amplero shuts down, lays off 17 employees
DreamBox CEO Jessie Woolley-Wilson at the 2018 GeekWire Summit. (GeekWire Photo / Dan DeLong)

DreamBox Learning CEO Jessie Woolley-Wilson is a quote machine.

As she explains the whys and hows of her successful math education software company, which raised $130 million in venture capital last summer, her ideas are precise and often packaged in clever aphorisms. (“To reshape the future of learning we have to work at scale,” Woolley-Wilson explained. When it comes to teaching kids, the company is “intent on building confidence as we’re building competence.”)

In recent years, Woolley-Wilson polished her message in stories in the New York Times, USA Today, Harvard Business School’s alumni publication, GeekWire and others.

But what her quotable conversations reveal is Woolley-Wilson’s crystal clear vision for what she is trying to accomplish with Bellevue, Wash.-based DreamBox and how she’s going to get there.

Woolley-Wilson’s father played a key role in her own path. A Haitian immigrant who came to the U.S. in 1956, he was a strong believer in the power of education to reach one’s goals. After earning an MBA from Harvard and working on Wall Street, Woolley-Wilson switched to the education sector, serving as president of Blackboard’s K–12 Group and of LeapFrog SchoolHouse, as well as holding leadership roles with the College Board and the test-prep company Kaplan.

She took the helm of DreamBox in 2010, where Woolley-Wilson said that she is “focused on reimagining education to unlock learning potential in all students, regardless of where they live… or who they are or how they learn.”

To do this, her company builds adaptive, online math lessons for students in grades K-8. The instruction responds to how a child is performing and adjusts the questions accordingly.

“We don’t see technology as a replacement for a teacher” Woolley-Wilson said, “but as a complement or a tool for a teacher.”

While ed-tech has in many cases promised much but delivered little, DreamBox has sought independent validation of their approach. The company has worked with Harvard University, Stanford Research Institute and others to prove that their instruction translates to measurable gains in student learning.

Woolley-Wilson credits their success to being based in the greater Seattle area where tech talent abounds and for being able to attract skilled technologists “who are looking for something purposeful in their life.”

To fuel DreamBox’s growth, she took care in choosing a venture capital source that would be a good partner, settling on TPG’s Rise Fund, a social impact VC whose investors include Bono and Richard Branson.

A screen shot of a sample lesson on fractions from DreamBox Learning.

“They were as serious about impact as they were about aggressive growth,” Woolley-Wilson said. With the cash infusion, the company can work on multiple initiatives at once, expand into more grades, add professional development for teachers, establish new partnerships and add staff, including a recently opened second office in Raleigh, N.C.

Woolley-Wilson is fired up for what’s still to come. I’m excited about our global possibilities, she said, “and changing beliefs about what kids are capable of. I’m excited about the appropriate role of technology in learning and I’m excited about inspiring the next generation of innovators.”

We caught up with Woolley-Wilson for this Working Geek, a regular GeekWire feature. Continue reading for her answers to our questionnaire.

Current location: Bellevue, Wash.

Favorite apps, cloud services and software tools: LinkedIn, Twitter, Confluence, Flowdoc, Zoom

Describe your workspace. Why does it work for you? Standing desk, huge white board, lots of chairs, large balance ball and portable elliptical machine. It facilitates discussion, courageous conversations, analytical problem solving, deep thinking and healthy support for long days.

Your best advice for managing everyday work and life? Tend to culture. People are the most important ingredient to company success, student impact and sustainability. It IS possible to do well in order to do measurable good in the lives of others.

Woolley-Wilson on a call at her Seattle office at DreamBox Learning. (DreamBox Learning Photo)

Your preferred social network? How do you use it for business/work? Twitter. Capture student and teacher impact; remind DreamBox teammates of how extraordinary they and their colleagues are. Remind everyone of how important this work of unlocking learning potential is and how it is inextricably linked to unleashing human capabilities to make this world a better place for everyone. We are all focused on first unlocking learning potential to inspire new levels of leadership both inside and outside of the classroom.

Current number of unanswered emails in your inbox? 20

Number of appointments/meetings on your calendar this week? Far fewer than a year ago

How do you run meetings? Begin by asking or stating the purpose of the meeting. End by summarizing action items and next steps and who is responsible for what. Try to connect people to the “why” of what we are discussing and let them figure out the “how.”

Everyday work uniform? Comfortable shoes (so I can walk my black lab Sonny whenever he or I need a break), comfortable clothes (ready for any kind of weather Seattle tees up), usually a light fleece or jacket to brace myself against the sometimes cold rooms in the office.

How do you make time for family? Schedule it and honor it. Let teammates know when I take time to feed myself in other ways than the work at DreamBox does and when I take time for family. When they know you do it, they believe you when you encourage them to do it for themselves.

Best stress reliever? How do you unplug? Long walks with my husband and Sonny; listening to/attending jazz music, international travel, moderating for the Aspen Institute; Several non-profit endeavors that support less advantaged kids.

What are you listening to? Nina Simone, Miles Davis, John Coltrane

Daily reads? Favorite sites and newsletters? Varies: NPR, PBS NewsHour, Huffington Post, New York Times, Wall Street Journal, Seattle Times

Book on your nightstand (or e-reader)? “Becoming” by Michele Obama; “Factfulness” by Anna Rosling Rönnlund, Hans Rosling and Ola Rosling; “Biography of Fredrick Douglass” by David Blight; “Long Walk to Freedom” by Nelson Mandela; Maya Angelou collection of poems

Night owl or early riser? Early riser. 2018 had a lot of late nights with the TPG transaction.

Where do you get your best ideas? Talking to and interacting with kids and young people. Long walks with Sonny and Dave.

Whose work style would you want to learn more about or emulate? Supreme Court Justice Ruth Bader Ginsburg

Like what you're reading? Subscribe to GeekWire's free newsletters to catch every headline


Job Listings on GeekWork

Executive AssistantRad Power Bikes
Find more jobs on GeekWork. Employers, post a job here.