DreamBox Learning Breaks New Ground

07 Aug 2018

DreamBox Learning Breaks New Ground

At the helm of one of the best-funded startups in education, its CEO is leading the way for black women looking to raise private dollars.

Re: Jessie Woolley-Wilson (MBA 1990)

Topics: Business Ventures-Business Startups Education, Information Strategy-Expansion Leadership-Leadership Style Demographics-Race-African American, Black Demographics-Women

A recent article in Fast Company details the $130 million fundraising round by educational technology company, DreamBox Learning, and profiles the company’s president and CEO, Jessie Woolley-Wilson (MBA 1990).

Woolley-Wilson traces her background—her immigrant father’s uphill academic battle in the pre-Civil Rights era and her experience with brilliant-but-disengaged classmates in Harlem schools—to explain her personal and professional interest in education, which has also included stints at Kaplan and LeapFrog.

Fast-forward to 2018, and Woolley-Wilson now runs one of the country’s most popular adaptive learning companies, specializing in math….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.

The article notes that the new funding will support expansion into new, international markets. The funding also puts the company—and Woolley-Wilson—in rare company.

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.

Last year, Woolley-Wilson spoke to the New York Times about her leadership style, which she described at “benevolent friction”—being hard on ideas, but soft on people.

"In a start-up, you don’t know what tomorrow will bring, so you have to be constantly learning and be adaptive with your colleagues. You might think you have a role to play, but you have to listen and be responsive to your colleagues in order for the team to really win. In the beginning, some people didn’t like it when I used that phrase because they felt that friction is a negative thing, and they didn’t want to have any friction with their colleagues. I would explain that if you don’t have pressure on the carbon, you never get to the diamond. You can still be very respectful, and assume everybody has a spark, but we have to subject our ideas to the toughest scrutiny because our work is important."