Jessie Woolley-Wilson’s career pivot into education technology began with volunteering.
Woolley-Wilson was working in banking but took the New York City subway to Harlem to tutor children. She learned a lesson that led her down a new path.
“It was not lost on me that there was brilliance everywhere,” Woolley-Wilson said. “Talent exists everywhere, but opportunity does not. For me, it was a passion. I thought it was going to be something that I would do in my volunteer activities, and it became a career passion.”
Woolley-Wilson, now based in the Seattle area, has spent the past 12 years at DreamBox as CEO, which sold a majority interest in the company to the Menlo Park, California-based investment firm Evergreen Coast Capital Corp. in December. The companies didn’t disclose the financials of the deal with Evergreen, an affiliate of the private equity firm Elliott Investment Management.
Bellevue-based DreamBox was founded in 2006. The company offers digital math and reading programs for students between kindergarten and 12th grade. DreamBox acquired the online reading program Reading Plus in August of 2021.
The Business Journal spoke with Woolley-Wilson about education, her career and her love of jazz.
About: Jessie Woolley-Wilson
CEO of DreamBox Learning
Hometown: Wilmington, Delaware
Education: Bachelor’s at the University of Virginia, M.B.A. at Harvard Business School
Interests outside of work: I love jazz, particularly female jazz singers. My husband and I have been going to the Monterey Jazz Festival. This will be our 22nd year, with two years off because of Covid. It wasn’t running.
What do you love about jazz? It tells the story of the African-American experience. I love jazz because it’s amazingly improvisational. It depends on collaboration and listening intently in order to do something special and unique. It creates space for difference. It’s one of the rare places that consistently I find a melange of culture, of age, of religion. It is diversity on steroids.
How has the Evergreen Coast Capital investment firm affected DreamBox? They see us for what we are. There are companies that are really more instructional companies with paper and pencil, more traditional. Then there’s a new generation that’s more driven by data and platform. That’s where we sit, and they seem to get that nuanced difference.
What pandemic-induced shifts in education are likely to stick around? It’s the $100 million question. I think there’s some things we’re pretty confident are not going to change. In the wake of the pandemic, a lot of schools had to adopt blended learning solutions like DreamBox Learning. There were a lot of new solutions that were adopted. ... The exposure and adoption rate of blended learning solutions went through the roof. I don’t think that’s going to retrench.
Anything else? The near ubiquitous access to devices and broadband. That is not going to change. These solutions enable different models. I know a lot of parents retreated to learning pods. Many of them have come back ... but how they used solutions like DreamBox will inform parental insights about what they expect their kids to have access to in a school.
Is there more of a push to market this through parents given how the pandemic pushed more parents to be active participants in their kids’ education? Our solution was really designed with the teacher at the center of it. We don’t want teachers to feel like this was a technology designed to go around them. We actually still believe the teacher is the most important influence in the child’s academic success.
Have you ever been tempted to go back into something other than e-learning? Never. This is purposeful work. We are going to change life trajectories, one child, one building, one district at a time. I really think it’s important work that is going to strengthen our democracy.
You’re on at least two boards, Quizlet and Class. What is the benefit? The boards that I focus on are in the education space. There are a lot of things that happen there that inform me as a leader here at DreamBox. There’s a lot happening (business-to-consumer) with the student as the purchaser. I get insights from my time at Quizlet about what is happening with the students.
What does the e-learning field still need to reach its potential? We need to inspire new models. What we’re doing at DreamBox, the dynamic personalization combined with job-embedded teacher professional development ... those things shouldn’t be anomalies. They shouldn’t be special. They should be an expectation because it represents the best way to learn. I think scaling successful platforms like that is really important.
What other major challenges are facing education right now? We have to think differently about who’s in front of a classroom. If the teacher shortages become chronic, and they get even deeper, we’re going to have to think about expeditious ways to get learning guardians ready to lead instruction. I don’t know what their profiles are going to be. I don’t know who’s going to lead that. I don’t know how quickly university teacher preparation programs will be able to pivot, but I think we need to be prepared for that. ... By 2025, more than 25% of students in school will be English language learners. You can’t have a teacher core that’s 5%. We’re going to have to close that gap as well.
What is one thing most people don’t know about you? I’m one of seven kids. Five girls and two boys. My father came to this country in 1956 from Haiti, and he met and married my mother.
Where did they meet? They met in a hospital in Kansas City. It means I kind of grew up with a global perspective. I grew up understanding the benefits of integrating differences. I also grew up understanding where there’s a convergence of values, amazing things can happen in full view of differences. One of the things we did really early here at DreamBox was codify the values.
This interview has been edited for length and clarity.
