How I Built This with Guy Raz - How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Episode Date: August 8, 2020

Guy speaks with Jessie Woolley-Wilson, CEO of DreamBox, an online math learning program for K-8 students. The platform has added two million new users during the lockdown, but that rapid growth has created "stretch marks" and new challenges for leadership. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders and entrepreneurs about how they're navigating turbulent times.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This podcast is brought to you by Squarespace. I talk to entrepreneurs all the time who are looking for a way to upgrade their digital footprint. Well, whether you're just starting out or you're scaling your business, Squarespace is the easiest way to build a great website that stands out. It's an all-in-one website platform that gives you everything you need to claim your domain, showcase your products, and get paid. Anyone can use Squarespace's cutting-edge design tools to build an online presence that truly reflects what makes your business special.

There are templates, intuitive drag-and-drop editing, and even an AI-enhanced website builder. Then, Squarespace's built-in analytics tools help you make smarter business decisions. Review website traffic, learn where to focus engagement, and track revenue all in one place. Looking to grow your business, Squarespace even offers fast, easy business financing

through Squarespace capital. Go to Squarespace.com slash built for a free trial. And when you're ready to launch, use offer code built to save 10% off your first purchase of a website or domain. Loans issued by Celtic Bank and serviced by Stripe, all loans subject to credit approval. This show is in partnership with Airbnb. This past summer, I took my family to Vienna, and it was incredible. We spent our days wandering the old streets, stopping for coffee and pastries, visiting museums, and just soaking up the history of one of the most beautiful cities in the world. And one of the things that made the trip so special was the home we booked on Airbnb. It had tall windows, beautiful old details, and plenty of space for all of us. And being in that home on Airbnb, right in the middle of Vienna, walking distance from so much of the city,

made it feel less like a visit and more like we were actually living there. Plus, taking a trip is the perfect time to host your space on Airbnb. Your place with all of its personal touches and its amazing location could make someone else's vacation even better. Your home might be worth more than you think. Find out how much at Airbnb.ca.com slash host. Hey, everyone, welcome to how I built this resilience edition. On these episodes, we're talking with entrepreneurs and other business leaders about how they're meeting this very challenging moment in new and creative ways. And today, we're going to hear from Jesse Woolley Wilson, the CEO of Dreambox.

Dreambox is an online learning platform that uses educational games to teach math to kids. And it's become more popular than ever, as many schools in the U.S. are opening back up, but only online. Jesse joined me from Dreambox's headquarters in Bellevue, Washington. So for people who aren't familiar with it, can you just kind of give us a description of Dreambox? Sure. Dreambox is K through 8. math program that delivers personalized learning for every child on it. So it's engaging. Kids think they're doing games, but they're actually doing very serious math learning.

So you have, I think, about 270 plus employees now. How are you managing the staff remotely? It's been a lot of change for us. So there were two phases of this evolution post-COVID. First phase was to survive. And the second phase was to thrive. And in the survive phase, we were guided by our company values and by three principles, really. The first is, what do we do to take care of our employees? We want them to be safe and secure. And we close the office early, early March, before many other people do. And then the second was, what do we do to take care of our school customers, our kids, and our teachers and school administrators?

And we figured if we took care of our staff, then we could take care of our customers. And then the third piece was, if we take care of our customers, then we will take care of our company. the default was not what do we do to take care of revenue. The default was what do we do to take care of our talent so that we can take care of our customers. If we do that, we will do everything we can to protect revenue in the company. So, you know, as the pandemic began to unfold and as schools really began to shut down quickly, what was the economic impact on your business? I mean, was there a slowdown? Was there a rush to sign up? What, what happened? So in the beginning, we didn't know what was going to happen. So we decided to prepare for the

worst and hope for the best. And so we cut back on all of our expenses dramatically. We moved everybody to work from home. That meant we weren't spending us much money on travel. We didn't go to any conferences. There was a lot of education conferences where we meet, you know, principals and district administrators. We cut out all of those. And we really cut out everything that we have relied on for the past 10 years to cultivate customers. And we didn't know what was going to happen. Then I got together with my team and I said, what do we do to help teachers through this? We have to figure out a way to demonstrate our partnership. And they said what we should do is open up the platform for free throughout the whole school year. Wow. They have many, many things to worry about. They won't have to worry about

math instruction. That will be one thing they won't have to worry about. So I went to my board. I said the thing that we should do is to open up the platform so that if a district had, you know, three of 50 schools on Dreambox, they could put the remaining 47 on. on for free through the end of June, just so that they could keep their kids learning at home. And we figured the best thing to do was to go to our existing customers because they were already trained. They had people in the district who could be resources to parents and to children, and we didn't know if we were going to be able to train them. So we did that. And within six weeks, we nearly doubled the number of students and districts were really desperate.

it. So fifth in five weeks. So that was over two million students that were added. So two million students added in five weeks. How much, so how many total students are using the platform? So over five million students, K3A are using Dreambox through our schools. Yeah. What does that mean for your product team and the engineers who are who are all of a sudden onboarding two million kids in five weeks? So I love that question because when I say that, most people say, oh, that's so great. You know, you had exponential growth. And what I say in response to that is when you grow really fast, you get stretch marks. And we got stretch marks. Yeah. So our stretch marks were our support system was overwhelmed. And this was at a time when they were usually, it was a low period typically. So gearing up for the fall, busy back to school season.

And so we looked at our team and we said, you're going to have to sprint now. And it was very, very difficult because it meant that we had to stretch ourselves. And the one thing I didn't mention earlier is part of. of our cost reduction, we moved everybody to a four-day work week. Wow. And so at the time that we moved them to a four-day work week, expecting very low volumes, expecting no sales, expecting nobody to use the system, we had an explosion of new customers, an explosion of kids on the system.

And I just told the team, you know, there's a lot that we don't know. I'm going to tell you what I know, and I'm going to tell you what I don't know. We're going to meet every month instead of every quarter. and I hope that with every successive month, what I know is going to start to creep up and be more than what I don't know. And a lot of people said, you can't lead like that. You can't tell people what you don't know. But people already know what we don't know. They need to know that you're going to be authentic about that. And they appreciated that even though I didn't have a lot of answers for them. So are you hiring? I mean, have you opened up positions?

So we put a hold on hiring for that survive phase. And now we have everybody's back to work. We came back earlier than expected. In early July, we came back 100%. And so now we are starting the recruiting process again. Wow. So I will tell you, Guy, though, we expected that all the schools were going to open up at least partially and maybe have, you know, Monday, Wednesday, and Friday in school and Tuesday and Thursday at home or some other kind of hybrid model. But in the last two weeks, we've seen an acceleration of schools deciding that they're going to stay 100% remote through the end of the calendar year. So that means that the teachers that we were going to train so that they would know how to use Dreambox are not in schools. So all of our professional development had to be

put on hold or used with a Zoom, for example. And it's really, as soon as you think you have something understood, you have to adapt because it changes and you just have to stay flexible. One of your, I mean, your main sales strategy is you deal with school districts and administrators, not parents. And I guess when you joined the company in 2010, there was this kind of more hybrid model where parents were targeted, the consumer was targeted, and now it's really school districts. I wonder whether now, if many parents decide to homeschool or to kind of opt out of virtual learning through their schools, is there a world where you start to pivot again and focus on consumers again?

Well, it's such a great question, Guy, because a lot of people don't realize, you're right. In 2010, we started to move toward the B2B model, but I didn't shut down the parent channel, the consumer channel. We knew that they were teachers there and administrators there in the parent channel and we thought that if we could win their confidence, it would help the institutional side of the business. So the other thing that we did is that we opened up Dreambox through the end of August now for parents. They could get a free trial so that parents who were working from home and being overwhelmed while they were at home would know that they could find a solution that was proven to be effective, that was engaging for their kids for mathematics with Dreambox for no

cost. We offered that trial for parents. And I don't think we're ever going to move away from parents. We think parents are the X factor. And we think technology should never be designed to replace teachers. 40% of the employees at Dreambox are former educators. We don't think that technology should replace the learning guardian. We think technology should do what technology does best, which is to help understand the thinking process of children and to give them actionable insights so that they can modify their instructional strategy and personalize it to be more high impact for every child. Let me go to a question from our audience.

This is from Giguna Hillary. She says she is volunteering as a teacher. She's been working with kids since schools have shut down. One disturbing thing she says she's noticed is that a lot of kids don't have access to online learning opportunities or their parents may not even know about them. How do you make what you do and sell available to every kid? So there's two things I would like to say here. It's really important. But one thing that keeps me up at night when I think about online learning is that it might widen the gap between the haves and the have-nots. And we all as a society have to be very intentional about making sure that we don't lose sight of that and that we work very hard to make sure that every child, regardless of their zip code, frankly, has access to great learning experiences. So one of the reasons we moved from the, consumer approach to the institutional approach is to bring Dreambox to every child. We brought Dreambox to where all kids were in schools, not just to the parents who happen to know about it, but to

institutions and communities where parents might not be aware of it. So that's one thing. But we need to make sure that some structural impediments like broadband access and device access are targeted to the least well-served communities. And what I'm encouraged by is that the CARES Act, and a lot of what districts are using with federal funds, is to address device and broadband access. Now, the good news is that almost 90% of kids have access to broadband and devices,

but that doesn't help the 10% that doesn't. So we need to work with libraries, and we need to work with foundations, and we need to work with private, public partnerships while we develop policies and funding mechanisms to close those remaining gaps. The last 10% is going to be the hardest, but we can never let up on that. When we come back in just a moment, Jesse tells us how a hybrid of in-person and online teaching can help all types of students do their best work. Stay with us. I'm Guy Raz, and you're listening

to How I Built This Resilience Edition from NPR. Hey, welcome back to How I Build built this resilience edition. And I'm talking with Jesse Woolley Wilson. She's the CEO of Dreambox. It's a platform for learning math online. This is a question from Noah Thomas. He asks, do you think that given that the marketplace for remote learning is already shifting and will probably shift even more post-pandemic? Do you imagine just an explosion of opportunity for educational technology companies in the next five, 10 years, maybe an accelerated a series of opportunities? I absolutely did. One of the things that we did several months ago was we studied the marketplace, and we studied industries that had V-shaped recoveries that were anticipated, U-shaped recoveries and L-shaped recoveries. So maybe a cruise line is not going to come back.

It's an L-shaped. Maybe an airline is a U-shape, but we really feel like education technology is a V-shaped. And we're seeing that now. We've had explosive growth in users, as I mentioned, and we expect that that is going to continue for the future because we feel like people who were trying out learning technologies as a nice to have complement now have been forced with distance learning to see it as a must have. And so if they have good experiences and they see that it complements what they want to do

in the classroom and at home, we don't see any end in the growth opportunities for proven, effective, engaging, and reliable learning technologies. Yeah. Are there public schools or school districts that you may know of, and I'm sure that you're consulted from time to time, is there a part of places in the United States that might potentially be ready to open that you know of? So this is such a hard question. I think that in the absence of a national strategy that will optimize frequent testing and tracing, it's very, very difficult to anticipate. when a school will be safe. That's the first thing. The second thing is there are conditions

and requirements for the learning environment, just like the home environment or the office environment that you would need to have in place. So do you have sanitizers? Do you have enough masks? How do you mitigate the risk with distance requirements? So all of those things need planning and I think the support of a national strategy

in order for parents. for teachers to feel safe going in there, for parents to feel safe sending their child there. And I don't think that many districts feel that level of confidence yet. As I said, a month ago, I probably would have anticipated that 50% of the districts will be returning in some hybrid model. I think that number is closer to 10% now. So I feel right now we're in a pause, and I feel like the next window is really after January to see how we get through the fall in the winter.

And once there's a vaccine in place and once there are effective treatments in place, I will have a different answer for you. But in this moment, I am not aware of any, many districts that are confident that they can send their kids back to school full time now. This is a question that we're also getting from Jitormoy Day via LinkedIn. Can remote learning truly work for all children? And can it ever replicate or even replace or be as good as? as in-person classroom instruction for children? So there's a lot of research that shows that the most important variable for student success is their teacher.

I don't think that's going to change in the long term. I think there are things that humans will do and continue to do that technology will not be able to do. I fundamentally believe that technology should be used to support human beings, humanity, versus the other way around. That being said, I think that we will not. not return to how things were before COVID. I think we're all moving and marching toward a new normal. And that new normal is going to have blended learning as a permanent feature of the best learning

because technologies can understand what is happening in a very nuanced way. And technologies can help personalize learning and give learning guardians actionable insights. What should I do to support Sally's growth in this moment? Dynamic information that should changes and adapts to what a child needs moment to moment. And it's that modality that will help kids with special needs, as well as, quote, the gifted and talented. I think all kids are talented. But for kids who need acceleration and are ready for more advanced work,

the system can help alert the teacher that when the child is ready and what specifically that child is ready to do. That's very difficult for even the best teacher in the best, resource school to be able to personalize learning instantaneously for 30 kids at once. But the nimble personalized learning technologies can do that very effectively at scale. And so the trick is to connect what the technology can do with the in-person learning experience to bring it to a new level. That's the trick. Yeah. You know, I'm so inspired by these ideas you're talking about, right?

this idea that all these incredible innovations now happening can make learning more accessible and more efficient. But a big part of me is also so worried because I think of kids who rely on school as a safe place. School is probably one of the safest places for most kids they can be during the day. It's where so many kids are fed. And I looked after. And so I had very mixed feelings about what's happening now as a parent myself and seeing it with my own. own kids, you know, seeing all the remote learning they're doing. Well, I would say that you're justified to be concerned, but I would also encourage you to be very hopeful about what might happen. We're at a precipice now, and so we can reduce the waste. We can reduce the frustration of children

who are bored to tears because they've already mastered a concept and they're ready to move forward, but the teacher isn't aware of that. And we can move to a model where the teacher can use the from a system like Dreambox to organize her class and do rotations so that kids who are advanced can be in one group or kids who are struggling can be in a different group and she can modify her live instruction to make sure she delivers exactly what that smaller group needs when they need it. I fundamentally believe that talent abounds and talent lives everywhere. It's that opportunity doesn't. And what we're trying to do at Dreambox is to bridge the gap between talent, an opportunity. We believe all kids are mathematicians. We believe all kids have a spark. And we need to

make sure that their learning environment is structured in a way and is designed in a way that we can show that not only to everybody else, but more importantly, to that child. We want that child to know that they can do anything that they want to do. I want to ask you one last question before we let you go about your leadership style. You've been at the company for 10 years. You're obviously experiencing incredible growth right now. You've led with a concept that you call benevolent friction. How does it work? So benevolent friction is trying to capture the importance of courageous conversations. We want to be hard on ideas, but soft on people. We believe our work is so important to democratize learning opportunity that we want to try to leave our ego aside and be willing

to subject what we think is the best idea or best innovation to the scrutiny of our peers who share our mission and share our values about unlocking learning potential. And so in order for you to do that with confidence, you have to be willing to subject yourself to the scrutiny of your peers and to hear that there are ways to make something good, better. We're in pursuit of greatness for all kids. So benevolent friction is really a signal that says, I'm going to have a hard conversation with you, but it's not really about you. It's about the idea. And it's about the idea that we think will help accelerate our growth so we can serve more kids and most importantly accelerate the impact that we can have to make sure that every child is successful in learning

math on Dreambox. I love it. Jesse Willie Wilson, CEO of Dreambox, thank you so much for joining us. Thank you. Happy Learning Math. That's an excerpt for my conversation with Jesse Willie Wilson, the CEO of Dreambox to see our full interview, you can go to Facebook.com slash how I built this. And if you want to see any of our other past live interviews, you can find them there or at YouTube.com slash NPR. If you want to find out more about the How I Built This Resilience series or join us live or hear about other virtual NPR events, you can go to nprpresents.org. This episode was produced by Candice Lim, with help from Will Mitchell, Tyra Lockhart, Matt Adams, Gianna Cappadona, John Isabella, Julia Carney, Neva Grant, and Jeff Rogers.

Thanks for listening. Stay safe and I'll see you in a few days. I'm Guy Raz and you've been listening to How I Built This?