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A woman of color CEO on overcoming adversity as a leader


  • Jessie Woolley-Wilson is the CEO of DreamBox, an online education company, where she’s had the opportunity to raise $210 million in funding.
  • She’s also faced a lot of challenges as a woman of color in a position of power.
  • She shared with Business Insider how she overcome adversity to run a successful company, and her advice for other C-suite executives and founders.
  • “It can get lonely in the C-suite, and people will start to tell you what you want to hear,” she said. “You have to surround yourself with truth tellers who know you and believe in you.”
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DreamBox CEO Jessie Woolley-Wilson remembered the moment clearly: It was early 2013 and she was waiting with several other entrepreneurs during a road show, hoping to talk to a group of investors. A young man got out of a car nearby, and it was clear to her that he was running late. 

“I need to check in,” he said to the group, “and I need a cup of coffee.”

Woolley-Wilson turned to look behind her to see who he was specifically talking to, only to discover that he was addressing her because she was a woman of color. He assumed she was a secretary.

“He was looking at me, and there was nobody behind me,” she recalled to Business Insider. “I was not happy, but I had to keep my composure.”

Woolley-Wilson remembered looking back at him and saying, “I don’t know where the coffee machine is. But when you find it, bring me one, too. I take mine black.”

Several hours later, Woolley-Wilson shared this story to a room full of investors. 

“We don’t expect people, especially women of color, to be in the tech space,” she said at the time. “My work isn’t just about math education. It’s about creating an educational system where people are raised to look at people who are not like them, and they still expect excellence. I want to unlock learning potential so we have more women and more people of color in every industry and sector, so more people get used to seeing women and people of color in every industry and sector.”

She said that her message was received mostly by silence. While she knew she’d been brave, the investors decided against funding her efforts after that session.

Despite setbacks like these, Woolley-Wilson has seen tremendous success as the head of DreamBox Learning, a software program that focuses on improving math education for elementary and middle school-aged children — the program now has over three million student users. DreamBox, which was founded in 2006, includes animated challenges, adventures, and games, with the goal of making math accessible to kids from all backgrounds. And Woolley herself has made waves recently by raising $210 million for the company, despite little experience with venture funding. She’s also become a well-known advocate for increasing diversity in tech, after her own experiences in the industry.

But her career hasn’t always been focused on education. In fact, she started her career in banking, a place where she said she often felt like the odd woman out, and where she didn’t feel like she was truly giving back to the community around her. 

“I remember buying Armani suits that didn’t fit my body shape,” she explained. “I did everything I could to look like a guy, including wearing uncomfortable clothes because that was the hidden rubric that seemed to lead to success.”

Woolley-Wilson remembered trying hard to make sure people saw her as capable, worthy of their time, and good at her job, so that when a new opportunity arose, she’d be considered. 

“They don’t teach you this! Especially if you’re from a family that isn’t part of that infrastructure,” she said. “You’re just trying to figure this out while your male counterparts see it easily. There are a lot of hidden figures who never rise to opportunity because they aren’t given a playbook.”

After getting her MBA, Woolley-Wilson decided to move into the education sector, to see how her business skills could help support education, bolstered by technology. Here, Woolley-Wilson said people were more used to female leaders, and there were a lot more people of color surrounding her. 

She worked at Kaplan, then Leapfrog, then Blackboard. Now she’s running the show at DreamBox. Still, she’s encountered myriad situations like the one with the coffee guy. She shared with Business Insider the lessons she’s learned over the course of her career, and her advice for women and people of color looking to move up, raise funding, and gain recognition in their respective fields.  

“This is good and bad for women, because some people don’t see leaders when they look at women,” Woolley-Wilson explained. 

She’s noticed that women are often obsessed with the competency of their products, but they tend to focus away from themselves during pitch sessions. That has to change if women and people of color want to raise money, Woolley-Wilson said: To attract the best talent and capital, you have to be comfortable focusing on yourself and being unapologetic about who you are and what you want.

You need people who will stand behind you, and Woolley-Wilson said she’s learned over the years that the money will come, but the relationships she cultivates are the most important piece of the puzzle. 

“Cultivate relationships before you need the money,” she explained. “You want to find people who care about what you care about. Investment is like a marriage, and you need to imagine them at your dinner table.”

Woolley-Wilson knows that it can be tempting to inflate your goals, but a reasonable metric for success is required when you’re seeking out investors — especially when it comes to finding more funding after the first 12 to 24 months. 

“Be realistic. Have a vision. And plan against it,” she said.

This includes being honest about setbacks, both within your current company and in your past. “Your mistakes qualify you to do this,” she said, which can be tough to embrace when you come from a position that traditionally carries less power. 

She remembered a time when she was wary of accepting her current role at DreamBox and she listed all of the reasons why she wouldn’t be a fit — times when her projects had failed and moments when she’d felt adrift. In the end, these mistakes were the exact reason why she was qualified for the role. 

“A mistake for an entrepreneur is a test for: Are you learning and adapting?” she explained.

As a minority, Woolley-Wilson believes it’s extra important to find a personal board of directors who will tell you the truth, even when it’s painful. 

“It can get lonely in the C-suite, and people will start to tell you what you want to hear,” she said. “You have to surround yourself with truth tellers who know you and believe in you.”

This also requires being receptive to tough feedback from that person or board of directors, which can be hard to handle if you’re already on the defensive or if you have long felt like there wasn’t enough interest in your ideas or products. But you need to learn to be humble enough to stop before you get defensive about difficult or negative feedback. “Success in life is about luck and your ability to have nimble intelligence where you can pivot quickly,” Woolley-Wilson said.

That diversity isn’t just important in your close circle, either. Woolley-Wilson believes that entrepreneurs need to focus on the data, which shows that bringing women and people of color into your company will make the company more successful, too. 

“The more we can get [people of color] proximate to those in power, the more we will improve,” she said. “We need excellence that looks like people like me so that there’s less fear and more opportunity.”


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