Skip to Main Content

Delivering Predictability: An Education Software Company Navigates Crisis

An Interview with Jessie Woolley-Wilson, CEO of DreamBox Learning
May 2021

The onset of the COVID-19 pandemic in March 2020 brought a unique challenge to DreamBox Learning, a leading provider of online math tools for K-8 education. Not only were both the organization and its people facing the pandemic and its unique uncertainty and challenges, but DreamBox’s fundamental industry had changed overnight. Schools closed, students shifted to remote learning, and parents took over home-schooling duties while many also juggled work.

For Jessie Woolley-Wilson, president and CEO of DreamBox, this unique challenge offered a once-in-a-lifetime chance to put her company’s values into action. After sending employees home a few weeks before the pandemic completely shut down the country, she made the decision to open up DreamBox’s product for free through the end of the school year — ensuring that DreamBox’s tools would be something parents and teachers could count on in the midst of uncertainty in so many other areas of their lives.

“The first thing we decided was that we were going to take care of each other, and second was that we were going to take care of our customers,” Woolley-Wilson said. “If we did those two things, we'd take care of our company. That's it.”

One year after the dawn of the pandemic, Spencer Stuart consultant Jason Baumgarten sat down with Woolley-Wilson for a virtual interview about leading through the twists and turns of 2020, and the steps her organization took to survive and thrive. The interview below has been edited for brevity.

How did the pandemic impact DreamBox? What do you think is the long-lasting impact of the pandemic?

Normally, you can ask people to stretch to get through a short-term crisis. But that wasn’t possible this time. Everybody was in crisis. How do you ask the team to stretch when they can’t stretch any more? As a leader, you had a choice. You could tell people to just suck it up — tell them that it's going to end and ask them to double-down, even though you didn't actually know when it was going to end.

I decided to do something different. I gathered my executive team together and told them that right now we know 10 percent, and we don’t know 90 percent. So, we’re going to be transparent. We’ll focus on what on what we do know, and we will earn their trust by being honest about how much we don’t.

The second thing was that we were going to be guided by our values. People joined this company because of our purpose, our values and our culture. We’re going to leverage that now. We have been investing in that since I've been here, and we're going to pull some out of the bank right now, because we need it.

So, we sent our employees home — early, in fact on the first day of March last year. From a customer standpoint, moms were freaking out, dads were freaking out, grandparents were freaking out. The lucky ones were the ones that had to juggle the career and homeschooling; those were the ones with devices, broadband, and some kind of agency to help their child or children learn. On the other hand, there were many families that weren’t so fortunate. The equity gap got bigger.

I went to my board and told them that everybody is in chaos. No one has any predictability about any aspect of their life, they’ve got a million worries, so we're going to deliver them one thing that's predictable. We're going to open up the platform for free. We're going to give them free access through June 30th. I wasn’t positive on the exact impact on P&L. But this is about doing what's right and living by our values.

When we opened up the platform, we didn’t put out one press release. I told the team, this is not going to be about DreamBox. It's going to be about our customers, and giving them comfort in chaos. Within 10 weeks we doubled the number of students on the platform. Frankly, we weren't prepared for that. When you grow that fast, you get some stretch marks. For us, that was the support function. We used to have one teacher for 30 kids, and maybe the teacher would call support. Suddenly, with forced distance learning, suddenly you've potentially got 30 home-based learning guardians calling for help.

A lot of leaders tell us that their teams are feeling tired after more than a year of the pandemic. How did you navigate that? How did you find new sources of energy?

I started by setting up a framework for people to understand and metabolize uncertainty. There were two phases. Phase one is survival. We didn’t know if we were going to be able to sell one new customer this year. We had big growth goals for the year, but suddenly we had no idea how long it would take - we just need to survive. The second phase would be to thrive in a new reality. I think that helped people shed their expectations about what they were going to do, and instead focus on that one thing: short term survival.

In June we took a breath and we knew what we were going to do. We saw that we were still able to sell, and that we were still able to reach our (school) district partners. Everybody had pivoted to Zoom, and we were able to see exponential growth. A calm came; the anxiety of the unknown had started to go down. There was stress, but it was about the known, not terrible fear about the unknown.

We were all experiencing a typhoon, but I knew on the horizon that there were calmer waters, even if we couldn't feel it. As a leader, I learned that I had to channel the promise of quiet waters to the team. People don't function well when they're anxious. I got into a practice of daily meditation and reflection, so that I could bring a calmer, more poised and more purposeful leadership, even if there was chaos around me. I really need to be disciplined to continue that, even when it feels like there are no rough waters, because there's something very restorative about meditation, reflection and a quiet mind that I didn't value before the pandemic.

How did you manage the social and political unrest of 2020?

One of my executives, a white male, unsolicited by me, started a monthly session where colleagues explore white privilege, unconscious bias and systemic racism. They have a conversation focused on structural racism, and people are invited to tell their stories. It’s one of our highest-attended forums. It's a beautiful thing to be an African American leader, and not have anything to do with it. That means we have a strong culture of decency, respect and dignity.

This also inspired a critical look at our software. Without knowing what we’d find, our technology group invited the people who build the product to explore whether there were hidden biases in our games. We didn't find anything. But the fact that he asked for it, and asked that they look at every single lesson, showed how we were taking the learnings from the meetings about racism and intolerance and applying it to our product and our business.

That group felt inspired that they were doing something important, and they were getting fed at work in a way that wasn’t happening in many other places. That good feeling creates reserves for the next challenge that comes. And they know what they’re fighting for: the continuation of a company that's an exemplar. The continuation of a company that's unlocking learning potential in every child, regardless of what zip code they're from. The continuation of a company with a cohort of professionals whom they admire, even in the toughest times.

When you think about your organization, what do you think has changed forever?

Before COVID we felt like we were pretty customer-focused, and after COVID we realized we have a lot of work to do. Being able to respond to a stated customer need is one thing, and that's the bar that a lot of companies use. True innovation is rooted in a level of intimacy with your customer that allows you to anticipate their aspirations. That’s a whole new game. That intimacy requires proximity. Brian Stevenson, the great civil rights lawyer, once said that proximity is a pathway to deeper understanding and deeper understanding is the pathway to empathy. At DreamBox now, we aspire to create empathetic experiences, solutions and products that honor the learner, and the learning guardians, and help them be who they want to be.

For example, what do you do for kids who live in a rural environment, where they are not close to a cell tower? They have structural impediments stacked up against them. We have that empathetic product, and we have to bring that to the forefront. And we have to make sure that we are looking at our learners and guardians as holistic human beings. Our goal is to make sure our technology serves the interests of humanity, and not the other way around.