Jessie Woolley-Wilson, president and CEO of education technology company DreamBox, did not originally plan on working in education. After receiving her MBA from Harvard, in 1990, she headed straight for Wall Street. Her parents had emphasized the importance of education, certainly–her father, a surgeon, emigrated to the U.S. from Haiti in 1956 and credited his own academic credentials with helping him succeed, despite the pre-Civil Rights limitations imposed on black men. But Woolley-Wilson had never thought of education as a career path until she started volunteering as a tutor for low-income New York City students.
“I would take the train up to Harlem and I saw kids who were brilliant, but who just hated school,” she says. “They didn’t think they could actually learn.” Without the influence of her parents and the stamp of approval conferred by her Harvard degree, she realized, “I could be just like them.”
Banking slowly lost its luster. “I remember calling my parents and saying, I promise I will pay you back every cent that you saved to send me to Harvard Business School,” she says. “It might take me the whole rest of my life, but I will pay you back. But I’ve found something that is actually important.” She took a job at Kaplan, later led the College Board’s interactive division, and eventually become president of the K12 division of LeapFrog, and then the K12 division of Blackboard.
Fast-forward to 2018, and Woolley-Wilson now runs one of the country’s most popular adaptive learning companies, specializing in math. (Adaptive learning harnesses technology to respond to students’ behavior and deliver tailored content, in real-time.) Across the U.S., Mexico, and Canada, DreamBox serves nearly 3 million students and 120,000 teachers. Today, the company is announcing $130 million in growth equity funding from TPG’s The Rise Fund, a social impact fund backed by the likes of Bono and Richard Branson. With help from Rise, DreamBox plans to expand beyond its core North American market as it pursues opportunities in Asia, the Middle East, Africa, and Latin America. In addition, former U.S. education secretary and Emerson Collective managing partner Arne Duncan, a Rise Fund senior advisor, is joining DreamBox’s board of directors.
“When you ask, where’s the greatest sense of anxiety, where is there the lowest level of self-confidence, it’s absolutely math. And that has to change,” Duncan says. He’s drawn to software solutions like DreamBox, to the extent that their impact has been proven, because of their potential to change the trajectories of entire districts. “The interest for me is scale, and is just trying to reach more kids, faster.”
The company structures its lessons around narrated games with themes like dinosaurs and pirates, geared toward students in kindergarten through eighth grade. As students progress through each animated adventure, they collect tokens for answering questions correctly. Teachers can focus the adventures on relevant subjects–fractions, for example–and tailor their instructional plans based on how students perform. If students race ahead or fall behind their peers, DreamBox’s adaptive model can serve up appropriate lessons, creating a more personalized experience.
“What we used to do is measure what happened to the average student in a district or a school,” says Rise Fund partner John Rogers, who focuses on education, says of the sector. “Now we’re measuring individual student performance. That creates an opportunity for supplementary providers like DreamBox to come in and support students who need help.” In math, he adds, the need is acute: “By middle school, more than half of the students in America are behind grade level in math.”
Schools have become savvier about demanding evidence of learning software’s effectiveness before buying student licenses (DreamBox costs roughly $30 per student per year, or $7,900 per school). But in many cases, that evidence is in short supply. The edtech website EdSurge, for example, includes over 150 math learning solutions in its elementary school product directory. Many are little more than digitized versions of multiple-choice quizzes and fill-in-the-blank worksheets, yet they are positioned to teachers as revolutionary.
“The skepticism educators feel about learning technology is justified,” Woolley-Wilson says. “We have as an industry overpromised and underdelivered. And what that translates to is when there is something that actually works, that is engaging, that is personalized, and that is efficacious, people don’t believe it.” Over the long-term, she hopes to “change the narrative.”
DreamBox took a first step toward that goal in 2016, when a report published by Harvard’s Center for Education Policy Research found that students who spent more time with DreamBox also demonstrated higher gains in math achievement. In addition, the report lent a vote of confidence to DreamBox’s adaptive learning engine, observing that students who followed the software’s recommendations “saw faster gains.” But it cautioned that there was no proven link between DreamBox and the higher scores, concluding that “evidence for the causal impact of DreamBox on student achievement is encouraging but mixed.”
With Rise’s $130 million check, DreamBox becomes one of the best-funded startups in education, and Woolley-Wilson becomes one of the only black women to have raised that much cash in private funding. According to Project Diane, just 34 black women have raised over $1 million in venture dollars.
Woolley-Wilson does not fit the standard profile of a startup leader in other ways, as well–as she says, she has a bit more gray hair. That is by design; Netflix CEO Reed Hastings helped lead an acquisition of the then four-year-old DreamBox in 2010, and shortly thereafter installed Woolley-Wilson, by then an experienced education executive.
Woolley-Wilson says the company will continue to invest in research designed to measure impact, a priority that The Rise Fund supports. She also remains confident in DreamBox’s underlying premise: supplementing traditional, “live” instruction with personalized digital lessons. “How does the best teacher in the best environment give individualized instruction, moment by moment, to 30 kids at once? It’s impossible without technology,” she says. “Our technology has created a pathway to do that.”