How Great Learning Happens - Jessie Woolley-Wilson, CEO of DreamBox Learning


Wouldn't it be great if you could instantly learn from your mistakes? While that might be difficult for humans to do, it's the foundation of DreamBox Learning's adaptive learning software which analyzes student errors in real time and instantly offers up opportunities to learn and succeed. But CEO Jessie Woolley-Wilson is quick to point out the system is intended to be a complement to live instruction, not a substitute for it. As her company learned over the last several months, it can also be a big help to parents who suddenly find themselves teaching their quarantined kids. Now the challenge is to make sure all kids have internet access as it becomes clear many schools will remain closed indefinitely.




SHIV GAGLANI: Hi, I'm Shiv Gaglani. Today, on Raise the Line, I'm happy to be joined by Jessie Woolley-Wilson, the CEO of DreamBox Learning, a leading education technology company serving millions of students with an adaptive learning approach to math instruction. 

Before coming to DreamBox, 10 years ago, she held a variety of leadership roles with top education companies, such as Leapfrog Schoolhouse, Blackboard, and Kaplan. Jessie, thanks so much for being with us today. 

JESSIE WOOLLEY-WILSON: Happy to be here, Shiv.

SHIV GAGLANI: The way I got introduced to you was actually a Harvard Business School (HBS) connection. I was in the class of 2016, and I was looking at people who had gone to HBS who were doing very cool and innovative things in education tech, and your name was obviously on the top, and I've seen a bunch of features of you and DreamBox over the years.

I explained a bit of your background to our audience, but in your own words, we'd love to hear what led you to your current role at DreamBox and education technology as a whole.

JESSIE WOOLLEY-WILSON: Sure. Well, I wish I could tell you that it was a planned progression and it really wasn't. I started my career in banking, and I had grown up always volunteering, doing some community work. It was just part of the family ethos. My father came here from Haiti in 1956, so pre-Civil Rights, and we really were encouraged to do everything we can to focus on education and to try to expand educational opportunities for those less fortunate.

When I got to Manhattan when I was working in banking, I kind of just felt like something was missing. I remember taking the A train up to Harlem to tutor middle schoolers who were brilliant! They lived in really challenging situations, but they were brilliant, and I said to myself, “Brilliance exists everywhere, but opportunity does not, and I'm going to figure out a way to use my talents and skills to try to democratize learning opportunity to try to unlock the learning potential of individual kids, really, so that we could unlock their life potential.”

I remember calling my parents. When you call immigrant parents, and you say you're going to leave investment banking, you don't necessarily get a high-five. I said, “I found my calling. I'm going to do something in education.” They said, “Oh, you're going to get a Ph.D.” “Well, not a Ph.D. I'm going to figure out a way to help learning guardians to help kids.” “Well, what does that mean? Does that mean you’re going to be a teacher?” “Well, I don't really know,” because when I got out of business school in 1990, a lot of people like us didn't go into education technology. 

It was a very formative space. It was very risky, so my advisor at HBS told me that I should get a shrink and to work it through because people didn't do that and blow up their careers. But it occurred to me that I was going to pursue perhaps a different kind of wealth and that I was going to be able to commit myself to something, even if it was really, really hard because I knew that the opportunities I had received extended from the zip code that my parents could raise their kids in.

That seemed like that wasn't good for those kids in Harlem, that wasn't good for their communities. I would argue it's not good for America, and it's not good for the world, so if we could figure out a way to unlock learning potential, we could harness human capability, and that was it. I had an epiphany, and I started out at Kaplan and never looked back.

SHIV GAGLANI: I can relate to a lot of aspects of that story. I'm a child of immigrant parents, and I immigrated myself. When I told them that I was leaving medical school to start a company…..it's not banking, it's medicine. You can probably relate to some of that as well.

JESSIE WOOLLEY-WILSON: That’s a higher fall than banking! (laughs)

SHIV GAGLANI: Yes, exactly, but now we employ doctors, so they are okay. How does DreamBox actually work? I know there's a lot of talk about machine learning, adaptive learning, and online education. We'll get into COVID and all the things that happened over the past few months, but just even before COVID, what exactly was DreamBox doing, and what differentiated you all? 

JESSIE WOOLLEY-WILSON: The thesis behind DreamBox is that technology can do unique things to support education. Even the best teacher in the best environment cannot dynamically adapt to what 30 kids need moment by moment. Even the best teacher in the best environment. So what happens when you don't have the best learning guardian, and you don't have the best environment? It's even worse.

The thesis behind DreamBox was to figure out a way to use technology to capture data about the learning experience dynamically and use that data to shape the lessons that each individual child would get. Literally, as a child explores mathematics in DreamBox learning, they are crafting their own individual learning path. What does that mean? I'll give you an example. 

You and I, Shiv, are both second graders, and DreamBox is trying to figure out if we know how to group numbers effectively. The platform will say, “Use the virtual math rack to build the number 37.” Your math skills are better than mine, so you say, “Oh, I have to make some tens,” so you take individual beads, and you make two groups of five. You do that pretty quickly. I, on the other hand, take 37 individual beads and move them along the virtual math rack. I get 37 right, and you get 37 right.

If we had a teacher in front of the room, she would say, “Both Jessie and Shiv understand grouping. Let's go to the next lesson,” but DreamBox knows that I didn't group at all. DreamBox knows I'm not ready to move on, and DreamBox knows that if I am moved forward, I will probably get frustrated. What DreamBox says is, “Wow! Shiv, he put this thing together really quickly. I'm going to test him for fluency.” 

Maybe there are 30 grouping exercises, and maybe you only have to do five to demonstrate fluency. Maybe I have to do all 30 of them. So this happens instantaneously, dynamically. We capture information from the live learning environment. We use it to inform the platform, and we then use it to personalize the learning instruction so that every lesson meets the child exactly where they are. It's never too easy, and it's never too hard. The net result is that kids feel successful. They love to learn even math, so it feels like a game, but it is anchored in the best fundamentals of math instruction.

SHIV GAGLANI: One reason this appeals to me so much is that the success of students in the K-8 stage in math, in science, can set them on a path in high school, in college to pursue STEM careers or not, so the impact that you all are working to have right now can help decide whether someone, fast-forward 10 years, even decides to take the MCAT or an NCLEX and become a clinician, which is where we're focused.

Can you talk a bit more about the scale you all have reached, and how many students and teachers, or learning guardians as you call them, how many of them have you impacted at this point?

JESSIE WOOLLEY-WILSON: We have over 5 million kids on the platform and about 200,000 students. We started partnering with schools and districts in 2011. There were some platforms out there that have been here for 30 years, and they have fewer students and fewer teachers, so it's hard to ascertain impact, but for us, we ascertain impact by student progression, by the actual growth that happens, and we feel like we're just getting started.

SHIV GAGLANI: You've worked at College Board, Blackboard, Kaplan. What attracted you to DreamBox and kept you there for a decade? Is it the algorithm? Is it the stage of the kid?

Also, do you have any metrics at this point that say someone who's progressed fast when they were in 6th-grade or 7th-grade math, fast-forward five years, and they take the SAT and more of them get into college or have more confidence? Do you have any of those kinds of metrics that you guys are starting to look at or already looked at? 

JESSIE WOOLLEY-WILSON: I’ll take that into pieces. The metrics are really focused. We started with little kids. We have four-year-olds on the system. I think longitudinal studies...there's a lot of opportunity for that and the connection between matriculation and success in college and life is yet to be measured because we're just kind of getting started, but we're hopeful because we collect so much data -- we collect about 50,000 data points per student per hour -- so we think that we'll be in a very good position to make high fidelity linkages between what they achieve in DreamBox and what they do after DreamBox, but our goal really was beyond mathematics. We wanted to instill a lifelong love of learning. We wanted to put kids into a supportive, customized, engaging environment that would encourage them to use their curiosity, to fail often, to learn from that failure, to apply the learnings from that failure so that they could actually succeed.

We like failure. The whole platform is built on error, mistake analysis, so why not allow kids to make mistakes? That's how the system learns. That's how we learn. We like when kids form their own hypotheses, make a mistake, and then use their curiosity to say, “That's not what I thought was going to happen. What could have happened, what might've happened, what should have happened?

That's how great learning happens. That’s what my engineers do at DreamBox Learning, so why can't kids make mistakes and learn from mistakes in a school setting? It's crazy. We need to inspire curiosity to inspire agency, to inspire a lifelong love of learning, and we think that that discipline might be incubated in math but go beyond math to other subject areas for their whole learning careers. 

We did anchor our platform, though, in independent efficacy studies. We had Harvard come in and do a study. This is something that people in this space really rarely did. It was an independent study. It was hands-off. They said that if a child uses DreamBox for an hour a week -- that's literally five lessons in DreamBox a week -- that they will get a 60% increase in growth compared to their control group. Sixty percent. 

We don't have to put kids on technology for hours and hours and hours. This is intended and designed to be a complement to the live instruction because we believe that technology should not replace teachers. It should support learning guardians and do things that technology is uniquely positioned to do that, as I said, even the best teachers in the best environment can't do at scale.

SHIV GAGLANI: Totally.  You preempted my next question, which is, you've obviously done a lot in math, and that's the foundation for so much that we do. Do you all have ideas about expanding into other fields -- science, English, or other fields like that?

JESSIE WOOLLEY-WILSON: The platform was designed to be grade, age, and content-agnostic. We have big plans, and we have other prototypes for other areas, other disciplines, but we wanted to be an exemplar. We wanted to be the best of the breed. We wanted to demonstrate that intelligent, adaptive learning was here to stay, and it was the way to deliver personalized, effective and engaging learning, so we put all of our efforts in a very focused way into making this the best of breed math product, but it's really a platform. 

You asked me earlier, why did I come to DreamBox? There's a story there. I was happy at Blackboard, and I got a call from Reed Hastings, the CEO of Netflix. He said, “Jessie, this is Reed Hastings.” I was vacationing with my family at the time on the beach and I was like, “Right, and I'm Michael Jackson.” He said, “No, this is Reed Hastings, and I want to talk with you about a very interesting company that I've seen.”  I'm not a founder of DreamBox learning.

He tapped me. He saw this technology at an ed tech conference and he said, “This could be transformational.” It was a B2C technology when he saw it. It was intended for parents to buy for their kids to give them an edge. He said, “If this is as transformational as I think it could be, we could end up widening the gap between the haves and the have nots, and that's not what we should do.” So he sought to find somebody who had been partnering with schools for a good chunk of their career. 

That was me, and he said, “I want you to come,” and I said, “Well, how big is this company?” He said, “I think it's about 11.” I'm thinking like $11 million so I said, “the chances of that working, Reed— I'm running a multi-hundred-million-dollar P&L. Why would I do that in my career?” He's like, “No, 11 people, Jessie. There are 11 people at DreamBox.” I'm like, “I'm not your CEO. I'll be on your board.” 

He's like, “I'm not looking for board members. I want somebody who speaks the business language, but also actually cares about education and can speak the education language to educators.” So I took a jump, I took a leap of faith, and I told him I would stay three years, then I would get on to something else, and in September I'll be at DreamBox for 10 years.

SHIV GAGLANI: Wow. That is an incredible story. As you were talking about the 50,000 data points that you monitor per student per hour, I’m curious, can you name a couple of the examples, for instance, time to answer a question. How do you monitor 50,000 data points an hour?

JESSIE WOOLLEY-WILSON: We monitor the decisions that students are making, so in that example that I gave earlier, the decision that I made to take individual beads gives me information about where I am in my learning path, how quickly I answer. Do I hesitate before I submit the answer? How many times do I make an error before I actually get it right? Am I struggling with the same kinds of questions that other kids are struggling with, who have made the same kind of mistakes that I've made? 

One of the things that the platform gives us insight into is the difference between productive struggle and unproductive struggle. We know that learning happens when things are hard, and so you can get to a point where the difficulty gets demotivating, so one of the things that we capture is how quickly students are learning and what their patterns of learning are. 

If I normally take three minutes to solve a problem and I'm taking six minutes to solve another problem, maybe it's getting to the point of the edge of productive learning, productive struggle, so DreamBox might pull me out of that lesson, take me earlier into the curriculum, reintroduce me to effective grouping strategies, and then give me a new problem and a new opportunity to be successful. 

We want to manufacture opportunities for all kids, regardless of zip code to be successful, and what we find is that even the kids from the least advantaged backgrounds in this environment, they're all the same, equal opportunity for learning, and they have a sense of agency, and they have a sense of commitment and persistence and they learn.

SHIV GAGLANI: That's definitely inspiring, and I'm very interested in learning more and actually going into some of the data that you all have. As a side note, do you all measure confidence of the students in any way, or do you use proxies for confidence? 

JESSIE WOOLLEY-WILSON: We use proxies for confidence, but we do also survey students. We have survey data, we have platform data, and it's gotten to the point where it's highly, highly nuanced.

SHIV GAGLANI: One paper we published that I think you may find interesting, or you're learning science people will for sure, is we looked at our audience of mostly medical students at the time. We looked at a million data points -- which is not much compared to how many you all have at this point --  about 1,000 students, 600 males, 400 females. 

In our platform, when you answer a question, you have to rate your confidence high, medium, or low before you answer, and we found that male medical students and female medical students are equally accurate but as you could probably predict male medical students are far more overconfident. 

Right now, that's just interesting. But there are studies on practicing clinicians who exhibit overconfidence and tend to misdiagnose and have a diagnostic error, and then the ones who were underconfident can do defensive medicine, which is not high-value care, so prescribing too many tests or CT scans when you can get by with an X-ray, for example.

JESSIE WOOLLEY-WILSON: Well, you're tapping around something that's very important, which is this notion about intrinsic rewards. At DreamBox, you can collect coins. What we find is that oftentimes girl learners will collect coins because their sense of satisfaction comes from amassing coins.

Oftentimes boys who are using DreamBox will take their coins then spend them, and they spend them so that they can get access to really fun games. They're still math games -- it's in the pursuit of fluency -- but they spend more, and girls save more, so part of what we are trying to do is understand what motivates a child to persist. 

If we can give girls more opportunities to collect more and encourage them maybe to take some risks and to pay for a game with their coins, they'll learn something different, something other than mathematics that might prepare them to partner with these boys when they are across the desk from them as engineers at DreamBox learning. 

SHIV GAGLANI: That's awesome, and then vice versa, maybe you can rub off on the boys and make sure the boys open up their 401k and start saving more. 

JESSIE WOOLLEY-WILSON: That’s right! (laughs)

SHIV GAGLANI: The elephant in the room is obviously COVID. Right now, in the news, there's a lot of debate around, “Should we reopen schools? What does that mean for online learning?” How does DreamBox see the last few month's progress, and where do you see the next few months going?

JESSIE WOOLLEY-WILSON: We are the lucky ones. We're not a cruise line industry with a U-shaped curve, and we're not an airline industry. We've seen that “V” curve and so we're watching it closely to see if the V turns into a W. 

We've seen an acceleration in our business, dramatic acceleration. Like everybody else in February and March, we were forecasting being down this year because we just didn't know what was going to happen. Schools were closing. We didn't know if we were going to have access to our purchasers. We didn't know if parents were going to be prepared to work from home and teach from home as reluctant learning guardians. We just didn't know, and, as we ended the quarter, it's been one of our best quarters in the history of the company. It's feeling like a V-shaped curve.

We're the beneficiaries of forced distance learning, but I think what's really happening is that a lot of people who were experimenting with personalized learning, distance learning as a nice-to-have, as an added benefit, shifted it into a must-have, so it is part of a continuity plan for districts. It might be a hurricane. It might be an earthquake. God forbid, it's another COVID, but they have to have a plan to reach kids and keep the learning going even if schools are shut down. 

That's probably part of why we at DreamBox opened up the platform and gave it away for free through the end of the school year because we knew that they were just going to do a lot of crisis management. People weren't going to be making strategic decisions about this vendor or that vendor, this platform, or that platform. So we got together, my leadership team, and we said, “What could we do to keep the learning going even if schools shut down?”

We opened up the platform, not knowing what was going to happen. People appreciated that. People got exposure to a very exciting platform that kids loved, that moms trusted and that teachers felt that they could partner with. It wasn't technology that was happening to them. It was a technology that was happening with them to augment their experience as a learner or a learning guardian. That really helped us, and as a lot of schools closed out the year in June, a lot of people said, “This has been a great experience. We want to continue with DreamBox,” and a free COVID trial offer turned into a client.

SHIV GAGLANI: That’s wonderful. Obviously, we don't know what the next few months will bring. A bunch of schools, some of them will be reopening, some of them may not depending on where they are. Are you, remind me, are you based in Washington, is that correct?

JESSIE WOOLLEY-WILSON: We are right outside of Seattle, and I have an office in Raleigh Durham as well, but we're watching what you're watching. We saw the news yesterday, LA Unified and San Diego districts announcing they won’t open for in-person learning in the fall. Up here in the State of Washington, Walla Walla school district also. We're going to see more and more of these districts announce that they are not going to have face to face classes, and they're going to revert to a distance learning platform, at least through the end of the year. You're going to see more of that, is my prediction.

SHIV GAGLANI: One issue with distance learning, though, is access to technology. Not all of them have the same amount of access to technology as, let’s say, people in 90210, students in that zip code. What are your thoughts on the ways that we can close the gap because of the uneven access to technology across K-8 students and parents?

JESSIE WOOLLEY-WILSON: This is the most important question that is facing people in this industry now. And this is the thing that keeps me up at night. At the end of the day, just like when Reed said, “We can't afford to have this transformational platform widen the gap between the haves and the have nots” we can't afford to have access to distance learning be the reason why the gap widens for the least well-served populations. At the end of the day, that's not why we're in business. 

I think there are a couple of things that have to happen. First and foremost, we have to have national leadership. We have to have a vision. We have to pull together private industry and policymakers to make sure that rural communities that don't have towers get towers. That if there is an opportunity to have free Wi-Fi in cities, that we implement it. That if there's a way to subsidize access for poor families so that they can have access to broadband, that we do it.

There was a time in ed tech where we thought devices were the pathway. We need to give people iPads. We need to give people Chromebooks. But now we realize it's really about connectivity, and we need to have an intentional national policy that makes sure that we can provide broadband access to the least well-served populations. That's the first thing. The second thing that we have to do is to figure out ways to empower libraries and other public areas to complement what can happen at home, but also to supplement what isn't at home because there are a lot of kids that are homeless.

There are a lot of kids that go to one place at the end of the day, and the next day they go to a different setting. Maybe, in the first setting, they have Wi-Fi, and in the second setting, they don't. There are a lot of kids that don't go back to two parents. We have to make sure that we adapt, and we meet kids where they are in life, just like the platform is trying to meet them where they are.

The last thing I would say for DreamBox is that we have to make sure that we create a solution that can leverage multiple pockets of funding -- municipal funding resources, federal funding resources, state funding resources. We have to take the extra burden to make sure that when we talk to our partners in schools and in districts, that they know that there is a plethora of funding that they can use to buy DreamBox. Even if they think of it as a curriculum, there's Title I dollars, there's E-rate dollars. There's a lot of different funding sources that will help them to pay for this in schools. 

Ultimately, we know that there are some states that are partnering with religious institutions in poor areas. Churches are used once a day, once a week, maybe three times a week. There are a lot of downtimes when those facilities that do have Wi-Fi are not being used. 

We have to figure out creative solutions to make sure that real estate like that -- that is not used often and fully, that has added capacity --  might be a backup for kids that don't have access at home. The last thing I'll say is school buses. A lot of kids go to school in school buses. Is there a way that we can wire school buses to have some productive time to and from school?

SHIV GAGLANI: Those are some wonderful recommendations. I guess I'm taking up more time than I asked for. My last question is mostly because you serve students and we serve students, although different age groups, obviously. If you were a student, whether it's K-8 or K-12 or college, what is some advice that you'd wish you could hear from someone during this really transformative and unprecedented time? 

JESSIE WOOLLEY-WILSON: This is an answer that might surprise you. If I were a child now, I wouldn't want people talking to me about technology. I would want people to listen to me and treat me as a human being with dignity and respect, and to know that I've been through trauma, I've been through some kind of trauma. My parents are stressed. Maybe my parents have lost their jobs. 

I need to go back to school because that's where I get my meals, or that's where I get my support from a learning guardian because I'm special ed, or that's where I get social- emotional services from school psychologists. That's where I get my shots from the nurse. We have to treat these kids like they're human beings and make sure that we understand that they have to be in a state of readiness in order to learn. 

That means it's Maslow's hierarchy. We have to make sure they're secure. We have to make sure they're safe. We have to make sure that they are well fed and that they are healthy and, therefore, ready to learn. I know that's not the answer that you're supposed to hear from a technology executive, but we have got to take care of the whole child. We have to take care of the trauma that they've experienced, and they're likely to continue to experience until we have a vaccine that is produced at scale and made readily available to even the kids that come from the lowest socioeconomic status environments.

Once that's possible, we can get back to scaling, innovative learning. But I think anyone who goes into schools at this time and expects kids to come back the way they left is going to be surprised. Kids are at a new normal, teachers are at a new normal, custodians are at a new normal. This is a societal crisis, and we have got to make sure that we create space for people to metabolize the stress and the trauma that they've been subjected to over the past several weeks or months.

SHIV GAGLANI: That's a really insightful answer at every level. Whether that's your employees at DreamBox coming back, or my employees at Osmosis coming back, or students going back to school. With that, Jessie, I'd like to thank you so much for taking the time to be with us today. It was a really insightful conversation.

JESSIE WOOLLEY-WILSON: My pleasure. Thank you very much.

SHIV GAGLANI: With that, I'm Shiv Gaglani. Thank you for checking out today's show and remember to do your part to flatten the curve and raise the line. We're all in this together.