“We Have To Cultivate ‘Anti-Racist Natives’ In The Next Generation.”​

Jessie Woolley-Wilson, CEO of DreamBox Learning, a software company that focuses on mathematics education at the elementary and middle-school level, shared powerful and inspiring stories and lessons with me and Rhonda Morris, the chief human resources officer of Chevron, for our interview series with Black leaders. The themes we explore include race in corporate America and how to increase the ranks of Black executives in the C-Suite (thus the B-Suite name of our series). Subscribe here for future interviews.

Morris: Who were the biggest influences early in your life who shaped who you are today?

Woolley-Wilson: It starts with my parents. My father came to this country from Haiti in 1956, and he met my mother, who is from Texas. He had an excellent education. We didn’t have much money, but they shared a focus on family and the importance of education. We were taught to believe that if we excelled and did our best, new opportunities would open up for us. They probably knew there were headwinds that we would face because we were people of color, but they didn’t burden us with that early on.

When I was in high school in Delaware, I remember going to the guidance counselor and telling her that I wanted to apply to the University of Virginia. But she said, “Oh, you won’t get in there. There’s only one or two people from Delaware who have ever gotten in, and you won’t be one of them.” I figured she was the expert, so I went home and I told my parents what she had said.

My mother said, “Oh really?” My father said, “That’s interesting.” And my father got up, made a phone call, and soon we were headed to my high school for a conversation with the principal. They said to him, “We’re a little confused. Our daughter is academically very successful, she’s an athlete in many sports, she volunteers, she did great on the SAT, and so we’re wondering why this fine institution wouldn’t encourage her to try her best even if ultimately she didn’t get into the University of Virginia.”

They were so incensed that I wasn’t even encouraged to try. Their ethos was always about trying your best, and if your best wasn’t good enough, see what you can do to improve your best so that your best gets better over time. I applied, got in, and the rest is history.

Bryant: What about early in your career? Key lessons there?

Woolley-Wilson: I had a manager when I was working in banking early on named Joanne Gallo. She told me at one point that I should apply to business school. I got an application from one school, but she kept pushing me to be more ambitious. She said, “I will not write you a letter of recommendation until you first apply to Harvard Business School.” I assumed I would never get into Harvard, so I was stunned when I was admitted.

I learned from Joanne that there are times when people see a spark in us that we don’t even see in ourselves. When I took her to lunch to thank her for the letter of recommendation and for the push, I said, “What can I do to ever repay you?” She said, “You’re going to be in a position where you can see a spark in somebody and sponsor them, even if they don’t see their own spark. If you have a chance to do that for women or people of color, that’s the best way you can ever pay me back.”

Morris: How has your upbringing influenced the culture you’re building at DreamBox?

Woolley-Wilson: One of our values at DreamBox is benevolent friction. We like to be hard on ideas but soft on people. It’s a value that takes some practice. First you have to believe that it’s safe to do it, but you also have to believe that it’s actually worth the pain it sometimes causes. I tell people that without pressure, carbon doesn’t become a diamond. We have to be willing to subject our best ideas to the scrutiny of people who have shared values and a shared ambition for kids, particularly kids of color.

So you have to leave your ego in the parking lot and then present your idea to your colleagues and just be ready for all the feedback that they have. People ask me why I’m so comfortable with this, because friction isn’t good. I grew up in an immigrant home, and we had aunties and uncles come by to talk politics and what was going on in Haiti.

There was just a very high decibel of conversation, and you were expected to have an opinion at the dinner table. You had to read the New York Times so you could have an informed opinion and participate in the conversation. It was very animated all the time.

When you’re a Black woman, intense can be misinterpreted.

When I started working, people thought I was too high-energy, too intense. When you’re a Black woman, intense can be misinterpreted. But for me, it was normal. Isn’t this how everybody talks to each other? So I tried to translate something that I was introduced to in my home into a company value that would cultivate and encourage innovation and create a safe environment for us to challenge each other.

In the wake of the killing of George Floyd, we’ve had a lot of courageous conversations at DreamBox, and most importantly, they’ve taken place when I haven’t been around. Our chief learning officer led a meeting about racial injustice and how it impacts learning. Our chief technology officer sat down with his team and said, “Let’s take a look at our software and make sure there’s no hidden bias.” I found out about these conversations weeks after they happened, and it made me very proud because they initiated those conversations on their own.

Bryant: Can you talk about some of the headwinds that you faced as a Black woman in your professional career? And what were the tailwinds that helped you get through them?

Woolley-Wilson: The main thing is that society puts masks on us, and the mask you wear as a Black American is that if you’ve achieved some success, people often assume it’s because of some benefit that you shouldn’t have received. They assume you don’t work as hard, you’re not as smart, you’re not as capable, and you don’t have the leadership qualities.

So there’s always a doubt and there’s always a sense that you have to do more to prove yourself. It’s a burden. You have to be “better than” in order to be treated less well. So you have to develop a thick skin. There are the hard impediments, like redlining and overt racism, but it’s not always the hard things alone that make people stumble. But it’s often the hidden, soft things that make us stumble.

For example, there weren’t many people who looked like me in the banking training program early in my career. I remember being invited to a dinner in the executive dining room. At the end of dinner, the senior vice president said to me, “I think you are going to go far.” I said to him, “We’ve only spent an hour together. Do you mind sharing why you are so confident that I’m going to go far?”

It’s often the hidden, soft things that make us stumble.

He said, “Well, I could tell you knew which fork to use and I noticed that you did not put salt on your steak before you tasted it.” The thing that people of color don’t realize is that we don’t even know what rubric is being used to evaluate us. So you have to have sponsors and advisors to watch out and explain what is really going on. A lot of people don’t succeed out the gate because they have no clue about what rubric is being used to evaluate them.

Bryan Stevenson [founder of the Equal Justice Initiative] says that all human beings are broken in some way, and everybody brings forth what they experienced as little children. If you can remember that everybody is bringing that scared, fear-based child to interactions with you, then you can have some empathy. But after a while, it gets old and it gets hard.

Morris: So what keeps you motivated?

Woolley-Wilson: I think about belief and progress. First, I believe I’m worthy. I’ve worked hard. I’m not perfect, I’m still growing, but I’m worthy to be at the table because everybody else at the table is not perfect, and they are still evolving, too.

Second, I think about John Lewis and the Edmund Pettus Bridge, and I think about when Martin Luther King walked across it. Most people who walked with him looked like me. But think about when Barack Obama walked across it, or when John Lewis went over it again last year, or what happened in the wake of the killing of George Floyd. Here in Seattle, there were a lot of people who didn’t look like me who were marching and carrying Black Lives Matter signs.

There’s still a lot of work to do, but this is an inflection point and things are going to change. I am optimistic about the conversations that are happening at dinner tables. I also believe in young people. The same reason we made so much progress with LGBTQ is because kids were having conversations at the dinner table about it. Just like digital natives do things instinctively, we have to cultivate anti-racist natives in the next generation. It will just be instinctive.

Bryant: Why is it so hard to talk about race, especially in corporate America?

Woolley-Wilson: We’re all human and we have habits, and it’s hard to break old habits and cultivate new ones. We should expect it to be hard because it is hard, and it’s supposed to be hard. That doesn’t mean it’s not important, and it doesn’t mean it won’t be successful. It just means it’s supposed to be hard, and it is.

We have to learn to be comfortable being uncomfortable. One thing I realize I’ve been doing over the past 20 years, which I shouldn’t have been doing, is that I’ve made my allies comfortable. What we need are active, reliable, courageous allies, not allies who we help make feel comfortable because they’re having conversations or they’re doing something philanthropically.

We have to ask those people who think they’re doing a lot of good to do more, because we need to engage those allies who have a heart for this, even if they don’t have the behaviors yet that are worth our investment. It’s really important for allies to know that they’re supposed to be uncomfortable because Black people have been uncomfortable for hundreds of years, and that’s on good days.

When people say they’re uncomfortable, I welcome them to the family, and I tell them that they must endure and they will become stronger from the discomfort. It’s just like when you go to the gym and build new muscles. The discomfort is the pain, but if we keep at it, we’ll get stronger and we’ll teach different lessons to the next generation, and they’ll do things more instinctively.

Morris: How do you cultivate these allies, specifically in the older generation?

Woolley-Wilson: I had a lot of support and mentorship and sponsorship from allies who typically were White men, many of whom happen to be Jewish. They supported me, put in a good word for me when people expressed doubt, and they had the courage and caring to tell me when I was doing something that I should stop doing.

So when I talk to young people, particularly women and people of color, I encourage them to cultivate their own personal board of directors. That board should be made up of people who believe in you, who believe in what you represent, who share your values and who are going to be additive to your career and life ambitions.

There are plenty of naysayers. We have to surround ourselves with believers.

And you have to be intentional about divorcing yourself from people who don’t support you or who don’t believe in what you want for yourself. There are plenty of naysayers. We have to surround ourselves with believers. So cultivating a personal board of directors is really important.

Sponsors and mentors don’t always have to look like me because they have access to places that I don’t have access to. Over time, maybe the two will converge and they’ll come together, but for right now, I welcome the sponsorship and mentorship of people who don’t look like me. I’m just going to ask them and expect them to participate in intentional, courageous racial justice initiatives that will move society and the world forward.

I raised almost $250 million over the past 10 years and most of it was from high net worth individuals, and venture capital and private equity firms. Reed Hastings, the CEO of Netflix, told me to make sure that my values are aligned with the investors’ goals. It’s not just about results. We’re working to help people and create a more just society.

Bryant: Besides building a personal board of directors, what career advice do you give to young professionals?

Woolley-Wilson: Find the thing that feeds you and have some courage about pursuing it. You don’t have to do it right out of the gate. You could start it as a side project while you’re paying your bills. But never give up on your heart’s desire because the thing that feeds you will get you through the tough times.

If you care about something and it’s really hard, it’s not going to feel like a sacrifice. It’s going to feel like an investment in your dream. If you’re doing something that doesn’t feed you, it’s just going to be painful.

And pay it forward. Don’t apologize for the luck and any favors that come your way. Embrace them, but embrace them with the intention to pay it forward. The last thing I would say is that if you’re not making mistakes, then you’re probably not pressing hard enough.

If you continue to repeat them, that’s something else, but see mistakes as learning opportunities that build your resiliency, skill set and judgment. You’ll see the patterns and you’ll make better decisions and judgments later in your career for having tried hard. Try your best, and if your best isn’t good enough, figure out why and make it better.

Be sure to subscribe here if you want to receive all our future Leading in the B-Suite™ interviews! And check out our previous interviews with:

• Carlos Watson, CEO of OZY Media
• Ruth Simmons, president of Prairie View A&M University
• Mellody Hobson, co-CEO of Ariel Investments
• Robert L. Johnson, co-founder of BET
• Ursula Burns, former CEO of Xerox
• Ron Williams, former CEO of Aetna
• Don Peebles, CEO of The Peebles Corporation
• Lloyd Carney, former CEO of Brocade Communications
• Lisa Price, founder of Carol’s Daughter

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