Jessie Woolley-Wilson is a quietly powerful force in education. For the past six and half years, she has led DreamBox Learning, growing the company from a startup into one of the leading providers of online math tools for elementary school children. Her steady but firm discipline of the company is a case study in how to grow an organization, especially in a complex industry such as education. She began her career as a banker but soon realized that to be true to her core beliefs, she wanted to have a role in education. That intentional choice put her on a more than 20-year path that led to her current post of chairman and chief executive of DreamBox.
EdSurge sat down with Woolley-Wilson this month at the ASU+GSV Summit, as part of our Thought Leader Interview series on the future of education. Below is an edited and condensed version of the conversation—or watch the full interview.
EdSurge: Jessie, you have become known for a few key managerial phrases, starting with this one: “Benevolent friction.” What does that mean and how does it play out at DreamBox?
Woolley-Wilson: Woolley: So we try to be hard on ideas—that's the friction part—but soft on people. We think our work is so important, this work in learning, so separating the work of modifying or changing the education system from actually creating stimulating, relevant, personalized, engaging learning experiences [matters]. They have to live in harmony, but they're different.
We think that work is so important that we have to be willing to subject what we think are our best ideas to the scrutiny of people who share our passion and who can make it better. We think the step to getting to a great idea is to subject it to intense scrutiny. So that means pressure sometimes, and I often tell folks at DreamBox that if you didn't have pressure on carbon, we would never see the diamond.
That's a lot of pressure! Tell us about an idea that you pressure tested at DreamBox that didn't hold up.
One example happened years ago, when were thinking about how to begin our work with tablets. I brought all of my expertise from oh, say, 15 million years in edtech, and I said, "Well, the infrastructure in K12 is very Windows-driven, PC-driven. We need to prioritize development with the tablet."
I had some engineers that said, "Well, in my home, with my kids in school, it's really iOS. Are you sure it should be Windows-based?" We couldn't do both. We had limited capital and we couldn't do both simultaneously. I said, "The wisdom of the world is that we really should start off with the (Windows) tablet."
So we began that work, but the intrepid folks at DreamBox continued to poke at that idea, to get data, to validate that data—and it turned out that I was wrong.
That’s a great example of staying focused on the big goal—moving to a mobile platform—but continuing to question the implementation choices, namely iOS versus Windows.
The main point here is not so much about the technology. It's about the courage and the comfort with saying, "Okay, our CEO is wrong, and we have an obligation to the kids to make sure we do what's right." I never want to be in a place where, because of title, great ideas are suppressed. So our team continued to press [the questions]. What's best about that example is not that I was wrong—because that happens a lot—but that there were a lot of people who knew what was right for kids, for learning, and therefore for DreamBox, and so they kept pressing until they were satisfied.
Let's talk about managing people. Much of management—whether in a company or university or school district—involves managing change, in bringing people on board with that change. Leaders get to make choices—but you must also inspire people to act on those choices. How do you balance between directing teams and drawing on the wisdom of the team?
I'm still working on this. In our education system, often-times people who find themselves in leadership positions are people who do something individually that's exceptional. But that's not really the pathway to launch long-term, sustainable adaptive growth. Sometimes we, as leaders, focus on the "how" of things: We may think we're doing things in a way that's suboptimal so we decide to change how we do things. We tell people, "Here's the design and the new design for the new way of doing things," and we focus on how.
But we totally underestimate what happens when you tap into people's passion. I'm somebody who believes that when you combine passion with purpose, amazing things can happen.
The way to tap into passion is through why. If you focus on why you want to do something different and what you want, in terms of a desired outcome, you may not even have to talk about the how. If people understand why you want to do something and what you want to achieve, what that north star is, they usually have better ideas about how to get there.
Sometimes when we think about change and people, we think about process. We say, "Okay, how do we change the process?" Then we make a plan to change that process and we notify the people. But I think we have to invert that paradigm: We have to start with the people and talk about why, and then ask them to help us plan how to do things. Then you step out and they focus on the process.
Share with us a time when you confronted a managerial knot, or problem, that wasn’t easily resolved—and what did you do?
When I first got to DreamBox, we were a consumer proposition. We were a K through 2 math program. Kids loved it and very well-educated parents loved it, but we knew it was a potentially transformational technology and a lot of very deserving kids didn't have parents who knew about it. So we made a decision to move from a consumer proposition to a schools-based proposition—something that was not a very popular pivot from an investor's standpoint.
It also meant we had to ask the people who made DreamBox a successful consumer proposition to change—to change maybe all the reasons why they came to the company.
So there were a lot of conversations about how do we figure out a way to partner effectively with learning guardians [namely teachers]. And we talked about how even though it's harder work, it's more important work with the promise of a bigger impact.
That sounds all great and rah, rah, but it's hard. It's hard to figure out how to sell to schools and districts. It's hard to figure out how to make sure people understand what intelligent, adaptive technology is and why they should actually care about it. It's hard to figure out how to do successful implementations.
And you know what's really hard? It's really hard to sell a new solution when you don't have 15 years or 50 years of efficacy studies saying, "If you use this thing, you're not going to martyr your kids." That's hard.
So getting back to leadership: You do the hard thing because you talk about impact. You can talk about [helping] a couple thousand kids, maybe tens of thousands of kids. Or you can talk about all the kids.
And when you talk about all the kids, you talk about unlocking learning potential of every child. That helps kids, that helps their families, that helps communities. I say it helps the nation. It's the way to protect this fragile democracy that we have. It's a way to make the world better. So when you talk about the why, then people can put up with some of the short-term pain because they know the long-term impact is big.
That's fabulous. Your story brings to mind another Jessie phrase—“nimble intelligence.” What do you mean by that?
What's hard about a startup company is that you need to hire really great people—but it's almost like education: You need to hire really great people knowing that you don't know what you're going to ask them to do in as little as six months’ time. They have to be able to adapt and shift and be excellent at [the new directions] even if they were hired to do something else.
It’s just like when we talk to kids about helping prepare them for, say, excellence in mathematics—but what we're really doing is teaching kids to learn how to learn so that whatever the next century throws at them, whatever industries are dominating the economy, they will not only survive the next situation...but will drive it.
That’s exciting. [That’s why I] look for nimble intelligence.
When people come to interview at DreamBox, we give them real problems to solve. And we let them talk to people at DreamBox ….We want to know how industrious are they? How curious are they? How smart are they? How nimble are they? How flexible are they? Do they listen effectively? We look for nimble intelligence because that gives us confidence that even as the demands of the business change, we can rely on our team to do different things than they might have been hired to do.
That relates to a recent DreamBox announcement: You recently said DreamBox is coming out with a professional development support tool for teachers to help them learn how to teach math. That wasn't something in your earlier game plan, was it?
Most things were not in the game plan. ...One of the things that's both encouraging and terrifying is ..asking your clients and customers not what do they need but what they aspire to do with DreamBox. That's a big question—but they tell you.
A few years ago, we had teachers say, "You know, it's so great that you're collecting all this information to inform the intelligent adaptive platform so that it can customize the learning path for students. But what about me? Why don't you share more of that information with me, as a learning guardian, so I know how to adapt that instructional approach? So I can be better at my craft?"
They were asking: Is it more important to feed the engine than it is to feed the teachers?
That’s a great, great question. It’s a hard question. Sounds like your customers were practicing benevolent friction and pushing back!
We started to think about it. At first, we thought: Well, we're a software company. We don't really know how to do professional development. People won't want to come to DreamBox for professional development.
And yet our customers were saying, "We trust you. We know what you're trying to do, and we've seen the impact on our students' motivation and their confidence and competence in math."
Particularly in grade school, most teachers are generalists. They're not math experts. So what could we do to get learning guardians closer to the content so that they could continue to adapt their craft based on the information we gave them about how students were learning mathematics?
So we had this question in the background. (Like all companies) there are many things you don't have the time or the money to get to. Then we had a conversation with the Gates Foundation, and they said, "What are some of the things you would like to do that you just don't have the time or the capital to do?" I said, "Well, I have this thing I keep getting poked about by my customers around what could we do to bring some of the intelligent adaptive capability to the adult learners in the learning environment.”
And they stepped up?
And they said, "Why aren't you doing it?" I said, "Because I can't prioritize it over this… or that.” And they said, "What if we partnered with you to accelerate the development?" So we worked in partnership with the Gates Foundation to apply intelligent, adaptive technology to the learning guardian experience.
What does that look like? Imagine you were a teacher and you had, say, 30 kids in a classroom. Five of them might be ready for more advanced mathematics than you were planning to cover in your class for the next couple of weeks.
What if you could know, through alerts, that you had a couple of students who were ready for parabolas, let's say. And you knew that, "Wow, it's been a while since I taught parabolas. I need a little refresher." What if you got the alert and you knew, not only that you had some students who were progressing to parabolas but you could press a button and see what lessons they would be exposed to? Or press another button to refresh your own understanding or teaching approach?
We want you to have actionable data about what is going on with the students in your classroom, and we want to empower you and build agency, so that you can do whatever you think you need to do. Maybe you're going to modify how you group students. Maybe you're going to do something different with one-on-ones and pull outs. Maybe you're going to assign different homework to them. You're going to have more choices because you're going to have a deeper understanding of where they are on their learning paths.
And we're going to take the sting out of it so that if one of those students comes up to you and asks you a question, you're not going to be surprised. You're going to have a sense of what’s next because you will have gotten an alert.
So this is just the beginning of what I think is the next generation in learning innovation…. bringing the learning guardian very intentionally into the process.
The powerful question we’re hearing from other organizations that have used adaptive software is this: How do you integrate the educator into the process?
We won't have a sustainable transformation in learning if we don't partner with educators. We need to lock arms with teachers—and I say that very intentionally as a head of a software company.
When we partner with our learning guardians, they schedule more time on DreamBox. And we know one thing: The more time students spend on DreamBox, the more progression they demonstrate. But it's all in concert with the learning guardian—because the learning guardian knows that child better than the technology “knows” that child. They're human beings, these children. It's a human learning environment.
If we can help the teachers be more comfortable with the content, be comfortable with best practices and blended learning and feel like they're the architects of the learning design...then that’s when both teachers and students soar.
Jessie, let’s draw back for one moment to the national perspective. Education goes through big pendulum shifts, from federal mandates to state and locally-driven initiatives. How do you feel about where we are right now?
You know what keeps me optimistic? I'm very much focused on learning, more than on changing the system. That said, I'm secretly very optimistic about the future of both. Why? Right now we largely live in a world where policy dictates practice. At the federal level, at the state level, at the municipal level. But what if practice could inform policy?
How do we get there?
[I’m talking about ] practice based on evidence of what works, under what conditions and why. Practice described so that others can emulate what works and understand the conditions for success, which are different from district to district.
There are a lot of solutions that are out there that people point to... but when you look under the hood and say, "Why is it working?" you don't get consistent feedback because we haven't applied the discipline of really understanding what’s working, in what environment and why.
We have so much data, such a deeper understanding of the success requirements especially in blended learning environments, that we can [use that practice] to inform policy at the highest levels and concentrate on those things that work.
For a long time in K through 12, the most successful companies were those that [would widely sell and district their products]. You could have a C [grade] product, but because you had distribution agency, you could make a lot of money selling it. I am very optimistic that we're on the cusp of an environment where the best box wins. Education buyers won’t have to make a martyr of their community because they can only guess at what tools will help.
This is still a little more futuristic. We still have to figure out how to get micro-evaluations done at scale so that you don't have to do a three- or four-year study to figure out what works and under what conditions. After four years, the conditions have changed. Leadership has changed. Strategies have changed.
And the kids have changed.
And the kids have changed, right. They live technology-infused lives. What interested them four years ago is not going to interest them now. The more we can have micro-evaluations, micro-assessments of what's working and distilled in a structured, intentional way, the conditions for success, the better we can identify what works, in great service to the students and teachers.
How do you think the Trump administration will affect the next four years?
This is a hard question for me. If you take a corollary and you say, "What will Jessie Woolley-Wilson do for education in the next five years?”—how do you answer that question?
If you say, "What will DreamBox do for education in the next three to five years?" then I'd have a very concrete answer.
I think we're spending so much time [fixated] on leaders when we should be spending time on the people that make up these organizations.
There are a lot of great minds in education. There are a lot of devoted people in the Department of Ed, and there are a lot of possibilities that exist today that have as much strength as they did [in the past]. So I don't really focus on the transient leader—and I don't want people to focus on me. I'm the least important person at DreamBox Learning. Our mission is more important than any one person.
I would argue that what we must do for learning in this country to preserve and grow our democracy, has less to do with any one person than it has to do with the collective will of the people, like the people collected at this [ASU+GSV] conference.
And the collective action of everyone?
And the collective action. It begins with belief. It begins with the belief that every child deserves an engaging personalized and highly efficacious learning environment. Regardless of what changes at the federal or state level, that [belief] will never change. That is what keeps me going every day. That’s what fuels my passion and what's going to deliver transformational, sustainable change for every kid, hopefully in this world, but certainly in these United States.
