Check out the exciting innovations for back-to-school. Learn more

Four Peaks – Jessie Woolley-Wilson Interview

HH: Is Education broken? With its budget cut backs and overcrowded classrooms? Can innovations save it? Jessie Woolley-Wilson believes it can. She abandoned a promising career in banking to pursue her passion for education technology two decades ago. In 2010, she was handpicked by the founder of Netflix to leads Seattle-based Dreambox learning . Now Jessie’s leading the way with the pioneer in technology, she says would radically transform the way the world learns. She even stole the stage from Bill Gates at the recent South by Southwest conference and that’s why Jessie Woolley-Wilson joins our exclusive list of “The Innovators”.  I’m Hanson Hosein, welcome to Four Peaks. Jessie Woolley Wilson welcome to Four Peaks.

JWW: Happy to be here.

HH: Harvard MBA, aspiring banking career- what on earth brought you to education technology?

JWW: You know it’s funny I feel like I’ve been in education all my life. You know, growing up my father came here from a different country – from Haiti. And I’m one of seven children. And education was just a very important part of our upbringing. And from an early age I tutored kid, to try to help them succeed. So we were encouraged to do community involvement in community programs and tutoring was what felt right for me.

HH: So you’re obviously there at an early age. During that you probably are doing the right thing by doing the banking thing after getting your MBA. What was it that made that light bulb go on to your head? And say – “You know what I want to go to that direction”.

JWW: You know even when I was in New York City, working at a big bank. I spent time volunteering at education- project literacy, tutorial program, and different things. Just to add to my experience and to keep me connected to the community. And I have the opportunity; I used to be an editor at the Harvard business school paper – Harvest. And one of my fellow editor who was on the tax side called me and said he just gone to couple educational centers and they were hiring MBA’s, to try to bring technology to learning to the test preparation. That’s really where I got my start in Education.

HH: So Catlin, Leapfrog and Blackboard – all these educational companies. Technology has been in education for a long time, but it only seems now to be hitting critically mass and now you’re the Belle of the ball in terms of conversations that’s happening with this. What happened?

WHH:  I think we’re in different time in history really. I mean for a long time technologies has been on the peripheral of learning. We’ve automated great books, so we’ve done things faster, but we haven’t had technologies that can impact learning at the point of instruction- real time. And so now, we’re leveraging the investment that the private sector has made and these referenced engines in technology. So Amazon or Netflix all of us has probably ordered something that we didn’t think we were gonna order, because these are technologies that get to know us through use. We brought that to Dreambox learning, so in Dreambox it’s kind of the technology that learns the learner, as the learner learns.

HH: How do you say that? And how does that make a difference in terms of the quality of learning?  Or even being to reach a certain level?

WHH: It’s really, really, important because what we are’ be able to do with this nimble technology is ascertain how a child is thinking by watching what they’re doing. So every click of a mouse, tells the engine something about what the child understands and what the child doesn’t understand. And so in real time, that’s what I mean by impacting learning at the point of instruction.  So real time when a child makes a decision we understand the strategies that they’re using to solve problems and we can therefore customize their learning path.

HH: What technologies exist now that this could not have been done say even ten years ago?

WHH: So these are these referral engines you know? That power things like your experience in amazon or your Netflix experience. So this are technologies that literally watch everything that you do, they have permanent memory and they have unlimited data. And what we’ve added to that at Dreambox is infinite patience. So imagine a teacher, great teacher that you had before when you were a little boy. And imagine why she was a good teacher. She inspired you, she was engaging, and she understood how to customize your learning experience. Now imagine that teacher in one classroom with thirty children. How is even best teacher in this circumstances able to know what every child needs instantaneously in every moment? That’s where technology comes in. Technology can come in and make that teacher more effective at what she does, even if she’s a great teacher. But very importantly if she’s not a great teacher, imagine what technology can do to make sure that that child gets exactly what they need, exactly when they need it. In a way that’s inspiring. So when kids are in Dreambox, they actually think that they’re playing a game -they love it! They spend a lot of time; they persist through challenge, because they’re doing exactly what they need when they needed.

HH: What that solution and the success you’re talking about imply is that the students aren’t necessarily will get any further, any longer from the classroom because something isn’t quite working. What is going there?

WHH: What is going on is really optimizing what is learning even in the best classroom. Let me give you an example: Say you and I are both second graders. You know? And you are just a little further along than I am. And we used a game in Dreambox to build numbers. And Dreambox says: try to use Math rack to build the number thirty seven and you understand that quickly. So you drag over three tens and a five and two ones. In four strokes you solved the problem. You don’t ask for help, you don’t hesitate for two or three sections. Seconds you just do it. I on the other hand, I don’t have this command- a vivid command of grouping of numbers and so I drag over single digits thirty seven well you get thirty seven right and I get thirty seven right. But should you and I have the same next lesson?

HH: No.

WHH: If we’re in the same classroom the teacher takes us both to the next lesson. Maybe that’s a lesson that I’m not ready for and I get frustrated. Or maybe it’s a lesson that you’ve already mastered. And you get bored. But she’s doing the best that she can do, because she can deliver one lesson. Imagine that situation where you’re supported with technology. And Dreambox sense me earlier in the lesson, so that I can get some training in grouping. So I learn grouping. I feel successful. I’m not frustrated. And you go to maybe subtraction module. Why didn’t you go to formula and subtract. You get what you need when you need it. I got what I need when I need it. It’s happening instantaneously at the same time in that same classroom.

HH: So what’s happening here then is that the technology not only is applying the motivation, but it’s actually taking the commoditization out of education and make it customizable. JWW: It’s the most supremely personalized learning experience available today. Seriously, I’m not understating it when I say that. And that what’s excites me about it, because not only are kids having fun, but they’re persisting through challenge and their driving their own learning. And they feel like they’re masters. Kids in low socio-economic situations who were planning on being engineers, encoders, maybe they’re gonna work in Seattle for us. You know? And then you have other kids that don’t feel held back. You know we have to figure out a way to inspire the young geniuses.

HH: Why is it specific to Mathematics in Dreambox?

JWW: Right now it’s Mathematics, but the engine was built to really accommodate any kind of discipline. But right now we’re collecting about fifty thousand data points, per student, per hour.

HH: Hmm… Well you know we’re gonna talk a little bit more about how Dreambox and other education technology is changing the culture of learning. Return with Jessie Woolley Wilson . We’ll be right back.

HH: We’re back with Jessie Woolley Wilson from Dreambox learning. Jessie, what brought you to Seattle?

JWW: Well Dreambox brought me to Seattle. In fact I remember when Reid was talking to me, about coming here.

HH: Reid Hastings of Netflix.

JWW: Reid Hastings. I was explaining to him that I didn’t know anyone in Seattle and that I heard that it rained there all the time. And I just asked my husband to move from California to Washington DC when I worked at blackboard. I didn’t think he’s going to be too excited about three thousand miles relocation. So I didn’t know how much I was gonna like it. Buts it’s a great place. It’s a beautiful place.

HH: For somebody who’s been in education technology in the business for so long. And we’re just going to play a little video of what it looks like within your office. What’s different or unique about the culture here that feeds or that even distracts from what you want to do with Dreambox learning.

JWW: Well there an amazing number of innovative of people her, inspired by the culture here. A lot of technology companies that get people different time at their careers, but then spin off and they create a second career. So there are a lot of people inspired by innovation and they want to do something that has a meaningful impact from the world. I find that there are a lot of people like that in this Seattle area.

HH: That’s great. Actually, I just realized were we’ve got a video of you were you were sort of creating some of the games and that you’ve got your dog in the office.  So you’ve got this sort of open not ordinary of culture of working here. Uhm… We’re both recently at South by Southwest, which has become a huge conference in Houston, Texas. Everything seems to be really focused on the future of education technology right now in this country. Why do we this national conversation now you think?

JWW: I think we’re in a unique time in History. And I think there are three things that are converging right now, that haven’t really converged this way in the past. The first is this submergence of this new class of technology that we’ve been talking about and what we call the intelligent adaptive learning. So there are new things that can happen, very powerful things that can happen. That can drive education to new levels. But secondarily a lot of schools are just under a lot of economic pressure. You know? They’re facing really economics tsunami and they are being forced to do more with less. This isn’t just episodic, because we got a bad couple years in our economy. I think it’s a new level of investment in learning. So they have to find ways to do more with less, to find productive and effective ways to teach more and more kids with larger spans of learning readiness. But the third and the most important thing that is happening now I think are changed expectations and permanently changing expectations in the minds of students and parents. Students live technology-infused lives every day. They are always connected, until they go to school. Most kids when they go to school are completely disconnected. And we say we’re losing our kids, they’re bored. Well yes! We’re losing our kids, they’re bored! I don’t think technology is a panacea, but I think it has an appropriate place in learning just like it has an appropriate place in living. And then parents want to prepare their kids for the 21st century and beyond. They don’t want their kids to just to survive the 21st century. They want their kids to drive it and to thrive in the 21st century. That means that kids have to have the skills to learn new things, to remake their skills set over and over again. Because we’re preparing kids for industries and jobs that don’t yet exists. So how do we prepare them for that? The best thing that we can do is prepare them to learn to master conceptual understanding of things, so that understanding can transfer from one job to another.

HH: And that preparing to learn is actually key, because the class room no longer have the monopoly over the actual educational process anymore. Technically speaking we may say that, we have access to all the information we need at our fingertips now right?

JWW: At our fingertips and then there are other things -that what happens at home compliments what happens in school because of software service technology that exist in the cloud. When I leave my classroom and then I log in at home, it knows where I left off. We didn’t have that you know in schools twelve years ago. So now we can make formally unproductive time very productive learning time. And it can be fun the whole time.

HH: Back to South by Southwest I just have your website up. There’s video of Bill Gates and you joined him on stage there. And a lot of folks were actually really impressed with you. What was it like actually? Really driving a lot of education reforms through the Gates foundation. What was it like to be working with Bill Gates there?

JWW: Well he is somebody who I think is inspired to make sure that we reach; we help everyone reach their human potential. So education is a piece of that mosaic. It’s not the only thing you know? He’s looking at healthcare and other things, but he’s really focused on helping people realize their human potential. And where he and I connect was, I believe that the first step in that is to make sure we realize their learning potential. Because then they can be anything that they want to be.

HH: Well we’re gonna talk to Jessie Woolley Wilson a bit more about how she reached her potential. We’ll be right back.

HH: We’re back with Jessie Woolley Wilson, CEO of Dreambox learning. Jessie, people of color in leadership positions in business are becoming a little bit more of common place in the United States. But having a woman of color in a leadership position specifically in technology anywhere is really unusual. What’s that trajectory been like for you?

JWW: You know I would say planned happenstance. I don’t think that I see myself first as a woman, or first as a minority. Although clearly I’m a woman and I’m a minority. But I feel like in education- education is a place different kinds of people come together. First in the classroom, and maybe on a sports field, and maybe as part of a teacher core, and maybe as part of a professional education core. So to be a woman in a minority in the field of education doesn’t feel that unique. When you put through a prism of technology then it starts to stand out. And I love every woman, every young lady, every woman to take coding – to take a coding class. You know? And to see it as a second language almost. There’s Mandarin. There’s Spanish. You know? Coding! You know, to create more opportunity and more pathways. I think that my kind of liberal arts background has helped me too. Because of my communication skills, to really maybe help people realize their potential who work with me. Because I can communicate with them I can connect with them, but there’s no substitute certainly going forward for not having more of an understanding of technology in general. Even if you’re in artistic career it’s gonna be touched by technology.

HH: Yeah, I think you’re right. You have identified two cultures that don’t necessarily always overlap. The education side where someone like you probably has bring great credibility because diversity matters so much in successful education, while technology just by happenstance unfortunately has been really sort of homogeneous. But that’s changing very quickly isn’t it? And you’re right bringing coding into it. When you think about your philosophy of education, there has been some resistance to technology and to touch devices. There was even in an article recently in Atlantic cover called the… You know?  Touch devices in kids.

JWW: Yeah.

HH: And whether we’re not actually, they’re not learning the use of device. How do you overcome that resistance?

JWW: You know we are really focused on what is gonna help students to succeed. There’s a famous saying by an anthropologist Margaret

Mead who said:  “If children do not learn the way we teach, we must teach the way they learn. And in this age and in our age that has to do with technology. Perhaps in a different age, it has to do with something else. But in this age right now, it has to do with technology. And I believe technology has a rightful place in education, just like it has a right focal place in our lives. I don’t think it’s a panacea, as I said. But I think (it can really), it has the promise to democratize learning. Because it doesn’t matter where you start; it doesn’t matter what your zip code means; it doesn’t matter what language you spoke in your kitchen table; it doesn’t matter where you begin. What matters is your pathway and how that pathway is enabled through the effective use of technology.

HH: That democratization is actually really interesting I saw you wrote recently about Sugata Mitra- who won the Ted prize for 2013. With his hole in the wall video, which is about basically how you can drop a piece of technology anywhere in the world even among poor kids in India and they will figure it out and surprisingly pass how it’s supposed to be used. How does that inspire you, when you think about learning and self-learning and being able to push education?

JWW: I think about how that’s gonna inspire or motivate, kids that otherwise wouldn’t have access to that. And I think that’s going to help them leapfrog problems perhaps, that they see for themselves, that they think it’s gonna prevent them from moving forward. This is about hope, the future is about hope. Technology in learning is about hope. It’s about what’s possible instead of what’s impossible. It’s about helping students and learning guardians- be their teachers or parents see past impediments to possibilities. Because they can know that more is possible when you can really understand how someone is thinking and therefore how they’re solving problems. And therefore, what they actually mastered in can transfer. It’s an exciting time to be in technology.

HH: So help me as a parent. I mean I teach this stuff. Students use this technology. I use it all the time. But my wife and I constantly question. You know how much access should we be giving to these kids? And this is the TV of our age right? And I hear what you’re saying. But I’m like (I mean) I worry sometimes about my kids being glued to this and not paying attention to the real face to face and the now.

JWW: I think it’s good to worry. I just think you shouldn’t be (uhm). You shouldn’t stop! You shouldn’t be stoic because of worry. I think you should be proactive, because of worry. So let’s empower children what they need, so that they don’t get victimized by technology. Let’s figure out what the right balance is. We don’t think that technology is a replacement for a teacher in a classroom. We think technology is a tool that will make that teacher, help that teacher, support learning better. We want to inspire new paradigm of learning. A learning that is student driven and is technology supported. But that ultimately results in student’s progression.

HH: Alright we’ll be right back with more words of wisdom from Jessie Woolley Wilson.

HH: We’re back with Jessie Woolley Wilson, from Dreambox learning. Jessie, it feels like the future is now with all these devices and what you’re doing with your company. But if you had to look ahead, say ten years from now? Given the intense focus we have on our education system in the United States. If you’re successful in getting people to sort of see the world your way- what do you think the classroom’s gonna look like?

JWW: So I don’t think we’re gonna be thinking about and talking about classrooms as we know it today. I think when we think about what can happen between eight o’clock and five o’clock or eight o’clock and three o’clock. And between four walls and a ceiling it limits our imagination. I think with technology and the new paradigm of learning is gonna elevate us outside of that structure. That limiting structure. And it’s going to bring worlds together. The classroom with the home.  None technology with technology. The students who really understands things well .The master and the novice. All those things are gonna start to blend and we’re gonna have very engaged, very fun learning that is age and grade agnostic. So you don’t get what you get in school, because of your age or because your gradeor your class. You get what you need because you demonstrated that you’re ready for it.

HH: It is very much like a videogame you don’t get to go to the next level, until you succeed the present one.

JWW: That’s right.

HH: That’s okay.

JWW: That’s okay.

HH: Because we’ve been stuck in this industrialized agrarian model for the last couple hundred years.

JWW: That’s right. And why are kids frustrated or feeling like they can’t learn? Every kid can learn. Every kid has a promise. It’s our challenge to unlock that learning potential.

HH: Well I love this world of no limits. This should be the last question in terms of you personally. If you had no limits, if you could cut yourself free of all bonds, of obligation and responsibility and expectation, what would you do?

JWW: I would be in education in some way. I would probably not say education actually. I would say, I would be in learning in some way.  I really believe that this world is gonna be more peaceful place. A more habitable place, a place that’s gonna last until the test of time, if we can figure out a way to unlock everybody’s human potential. And I think that is inextricably linked to our ability to unlock their learning potential.

HH: So what you’re telling me, by answering that is that-that crazy philosophic question. Is that you’re already living the dream.

JWW: I feel so lucky that I’m doing purposeful work. That I didn’t have to wait until I retire to do purposeful work. I’m absolute committed to this vision and when I see the impact on kids, when they throw their arms up in the air and they say “Even I can be good at Math” with Dreambox.  It doesn’t get better than that.

HH: Well Jessie Woolley Wilson, thank you for showing us the way and perhaps what the possibilities are with education. Thank you for being here. We invite you all to extend your bridge by connecting with us at . I’m Hanson Hosein.