DreamBox CEO Jessie Woolley-Wilson spoke with Education Lab about the challenges of being a black woman in corporate leadership, and about how technology is shaping the future of education.

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When parents and researchers debate the place of technology in schools, they tend to picture men like Bill Gates — white guys who grew up with money and found few barriers on the way to making more. But one of the most recognizable names in education software — DreamBox — is led by a black woman born in Texarkana, Texas.

Jessie Woolley-Wilson spoke with Education Lab about navigating the corporate landscape when you look different, and how she sees technology shaping education in the next decade. This conversation has been lightly edited for space and clarity.

Q: A lot of our coverage in Education Lab has noted the importance of human relationships in learning. Given this, how do you see the role of technology in education?

A: I don’t believe technology will ever replace a great teacher. But there’s a science and an art to teaching. When you have seven languages in a classroom and huge diversity in student readiness, how can a teacher make sure every little Jessie gets what she needs? It’s not possible. With technology, that teacher can divide her class into thirds and deliver live instruction to a much narrower band. Technology can help more teachers get back to the art.

Q: You grew up in a home of modest means. Isn’t there a risk that technology will exacerbate a class divide among in public schools?

A: This is one of the things I worry about most. We used to define success in technology as access — every kid will have a laptop or whatever. But if you posit technology without supporting great teaching, you will not succeed. My vision is that someday every child will have an IEP — that term has implications because of its association with Special Needs — but an individualized education plan for every kid, why not?

Jessie Woolley-Wilson. Courtesy DreamBox
Jessie Woolley-Wilson. Courtesy DreamBox

Q: How do you see education technology 10 years from now?

A: I don’t think schooling is going to be limited by four walls, a door and ceiling. I think we’re going to move rapidly and permanently to an anytime, anywhere model. Students will be much more involved in the acquisition of knowledge, and it’s not going to be age- or grade-defined. It’s going to be about mastery. If you have fourth graders ready for sixth-grade content, technology will facilitate that. It’s not going to depend on what you can do between 8 a.m. and 3 p.m.

Q: You’ve described your biggest career challenge as being a black woman in executive leadership. How do you handle this?

A: People have expectations of me that are different because of how I look. You can view that as something that holds you back, or as an opportunity. Here’s my advice: Do not assume malice. You encounter it sometimes, but nine times out of 10, people have good intentions.

Second: Have a very high bar for your performance. Don’t feel badly that you have to be better. We have to demonstrate that when someone’s investing in us they’re not doing us a favor. It’s a bit of a burden, but also an opportunity to develop great skills.

Third: Be honest. If you encounter a shortfall, don’t default to “It’s because I’m a woman or a minority.” Ask yourself what could I have done better? You can usually find one or two things — even if you trust your gut that something else might be going on. Then it doesn’t become a humiliating experience. It becomes a learning experience. You adapt and get stronger.

Q: Any advice for other young women of color hoping for careers in business or technology?

A: Be prepared. Kids often ask me, what language should I learn? I always say Spanish or Mandarin. And learn how to code, even if you never pursue engineering — it’s going to be a life skill.

Also, when you seek mentors, don’t limit yourself to people who look like you or have the same background. You could be cutting out a huge source of support. And never lose your sense of humor. Anger is easier. But it shuts down communication and possibilities.

Q: Do you have a favorite book?

Citizen: An American Lyric,” which is about subtle racism. I think it can have a profound impact on how people experience and understand race. As a country, we’re still struggling to have a productive dialog around race, and I’m hoping books like this will help people find the words for that discussion.