Podcast: Jessie Woolley-Wilson on Intelligent Ed Tech

We’re listening to the Getting Smart podcast where we unpack what is new and innovative in education. We’re your host Jessica and Caroline. Yep, you heard that right. The duo is back. Caroline missed you and I finally let her back in the podcast studio. In all seriousness, we are back in action and excited to bring you today’s episode from our own backyard, Bellevue Washington. We recently went to Bellevue to talk with Dreambox CEO

Jesse Woolley Wilson. At Dreambox Learning, Jesse Woolley Wilson has overseen the growth of the adaptive math learning platform that now serves 3.5 million students. She’s been a leader in ed tech for more than two decades. Let’s listen in as she and Tom talk about their work supporting teachers and the road forward. Jesse Woolley Wilson, welcome to the Getting Smart podcast. Happy to be here Tom. Why did you study English at UVA? You know,

my parents, I’m one of seven kids and my parents believed in a liberal arts education. They wanted, they encouraged us to have a general education in undergrad and then to specialize in graduate school. So why did you pick business school? Why did you go to Harvard? I really went to Harvard. That was planned happenstance. I went to Harvard because I had a manager when I was in banking who told me that I was good at this business thing and that I should apply to Harvard Business

School. I told her that I didn’t think that was going to happen. I would never get in and that I would go to pace at night if it would satisfy her and kind of make her leave me alone. And she said, you will apply to Harvard Business School. If you don’t get in, we’ll talk about it. And to my shock, I was at, I got in and got on a new trajectory. Was it a good experience? It was a great experience. It was a great experience because it was a Socratic method. It was a great

experience because it was about solving problems. It was a great experience because it wasn’t about producing data. It was about the interpretation of the data and the implications of the data. You know, not data for data sake, but data for action and decision making. And it was a great experience because it was a global community. I always consider myself a great success. How many African American women were in your class?

Not enough. Yeah, but More than, fewer than on my hand. So if you go to the best business school in the world, why on earth did you pick ed tech or education more, more broadly? Didn’t somebody tell you that it could be easier to be funny? Another industry? You know, because you’ve been doing this for almost 30 years, right?

Like 24 years. Yeah. So I started out in banking, as I said, but growing up, we were asked to volunteer in some way and to give back to the community. And I kind of like school. So I tutored kids. And when I got to New York City, I didn’t really feel fulfilled by the work I was doing in banking. And so I started tutoring. So I remember taking the A train up, you know, about six o’clock at night to go tutor some kids and then taking the A train back

downtown and going back to work. And I felt renewed after that. And what occurred to me was when I saw these middle schoolers that I was tutoring, and they were telling me about these complex businesses really that they were running in their communities. I said, what is the difference between me and these kids? I had excellent parenting and shepherding and I had access to an excellent education. They had an they had an MBA of life that showed resiliency and innovation.

They actually were more successful doing what they were doing than what I would have been in their place. And I said, this is this is a tragedy. It’s a tragedy for them as individuals. They don’t see their brilliance. It’s a tragedy for them as resources for their community to lift their community and to solve local problems. And I would say it was a waste of talent for this nation. So that’s when I decided that I was going to step off. And I joined the Stanley Kaplan group,

the Washington Post had just purchased Stanley Kaplan and they hired a bunch of HBS grads to manage different parts of their business. And that’s how I got started. So you were a Kaplan for a couple years. You’re a league prog for a few years. Yeah. You’re on Blackboard for three years. Almost five years. What was your favorite job before Dreambox? So I really enjoyed LeapFrog because it was the nexus of technology and content.

I also enjoyed it because it was about young children and I feel like we get a really good return on investment when we start young. So what I learned at LeapFrog was that if you can engage students and make them enjoy things that were challenging, then they would persevere through that challenge toward proficiency. And if you made sure that you locked arms with teachers, then you wouldn’t have to worry about figuring out what to do with your

product. Your teachers were your weather vane for what you should do next. And so I went to places like Blackboard to understand the power of software as a service and to understand how to leverage the internet to democratize opportunity by bringing affordable scalable systems. And so coming back to Dreambox after having a couple stints, I got back to the young kids, which are my passion. I got back to content plus technology and I was able to leverage what I

learned for software as a service to try to scale something to make sure that it got to every child regardless of kind of their socioeconomic status. So you’ve been at Dreambox for nine years? Nine years. But the company was started in 2004. 2006 before I got here. Yeah. What’s the origin story? So Dreambox was formed by a couple of founders that were former Microsoft executives and they had a notion that their kids, even in the best schools available, were not going to learn next

generation skills, you know, problem solving skills, critical thinking skills, deep thinking skills. And so they birthed this company, which was a B2C company, and decided that they were going to sell it to parents. It’s a very difficult business model unless you’re going to spend a lot of money in advertising. Was Luke Greg one of them? He was. I think Luke came to visit me in 2005, 2006. Yeah, I’m not surprised. They should have. And I was really excited. That was one of the first

times that I had heard of an adaptive engine. I thought it was really cool, the idea, you know, calibrating learning to a learner’s level. Yeah. So it, we really… Yeah, they pioneered intelligent adaptive technology. And there are a lot of companies that say they’re adaptive, but what they mean by adaptive is adapting pace in place. So your math skills are better than mine. You and I start in lesson one, you get done lesson one and show

proficiency in a third the time that I do. Don’t ask for help. Don’t really need much scaffolding. And you move on to lesson two. I struggle immensely. I ask for a lot of help, get a lot of help. I finally get to an area where I can actually proceed and I go to lesson two. And my lesson two is the same as your lesson two. That’s what they call adaptive. That is not what Dreambox means by adaptive. And Dreambox, that would never happen. So Dreambox would see that I was not ready

and I was struggling. It would pull me out of that lesson, take me earlier into the curriculum, give me scaffolding that is really appropriate, and then give me a new problem and a new opportunity to succeed. So before I get frustrated and engage in unproductive struggle, Dreambox adapts to where I am and makes sure that I get exactly what I need when I need it. You’re sent on and you might go and your learning path is literally architected by your readiness for it and yours is going to look

completely different than mine. That is what we mean by intelligent adaptive learning. We literally measure how kids are thinking, how they’re answering problems, and our adaptation includes pedagogical adaptation. Most solutions don’t do that. Just level adaptation. Level and pace is usually what they mean. So when you got here in 2010, they were like 12 feet long, right? 11. Well, when you got here, it was 11. Yeah. Why would you leave? You know, you had a big company,

so what was the promise that sparked your interest? I have a mentor who told me it was madness. It was a fever. I was tapped by Reed Hastings. He had seen this technology at the GSB conference and was looking for somebody who could help him bring it to schools. He thought that if it remained as a B2C solution, it would remain in people who were well-healed, you know, Microsoft executive kids and families like that. And he thought at the end of the day, if we didn’t bring

it to schools, we would actually exacerbate the gap between the haves and the have-nots. So he wanted to pivot and make it a B2B. And he needed somebody that had some passion and experience for partnering with schools. And so he tapped me when I was at Blackboard. I remember saying, why would I do that? Do you want me to be on your board? He’s like, do you have $10 million? So that wasn’t a possibility. And when he basically said,

take a look at it, take a close look at it. And if it’s not worth your passion and your talents, then I’ll try to find somebody else. And I took a look at it. I talked to some superintendents who are just, you know, who were just people that I trusted in each of my career moves. And most of them hadn’t heard of it, but all of them liked it. And that was very significant to me because it was just a K through 2 solution when I got here. And I’m like, why would you like it

when you can’t even implement it across all of your elementary schools? And it was because of what you said. It was fresh. And it was truly adaptive. And it was a different paradigm for learning. So I took the plunge. I left Blackboard and moved to Seattle and started adding some muscle to it. So it could be used in a one to many application in a classroom. And we began our work to continue to build up a curriculum and build out the administrative function so that it could

be used as an essential tool in the classroom. So if we fast forward to today, you have like three and a half men kids on the platform. How many teachers is that 130,000 teachers? What is it? How would you describe what Blackboard is to somebody sitting next to you on an airplane? Dreambox. So Dreambox is a K through 8 adaptive math platform that delivers personalized, engaging, and efficacious learning experiences to students. In addition, it provides actionable insights to

teachers or what we call learning guardians so that they get insight into how a child is thinking, where they’re struggling productively, where they’re struggling unproductively, and they can complement and modify their live instruction based on the data that they get from the system. Earlier, we were talking about good products and good deployment and the difference between good products and bad products and good deployment, bad deployment. Let’s talk about

good product versus bad product. Why do you think Dreambox is a good product? How do you compare it against the other alternatives that are out there? So the ed tech industry is kind of hampered by over promising and under delivering over the last couple of decades. And one of the things that’s distinctive about Dreambox is that it delivers. So we subjected ourselves to third party scrutiny and had independent evaluators take a look at our system at a typical implementation

of our system. And it showed that with just five lessons a week, students could get meaningful progress on Dreambox learning and outperform their counterparts who don’t use Dreambox. So really up to an hour a day, be it the Harvard study or the SRI study, there’s several studies out there, essa.org. It shows that we are efficacious. And so that’s something that most companies don’t do because it’s risky. That’s one thing. The second thing is we understand engagement. A lot of people

think about this as a game. We don’t think about it as a game. It’s serious fun. But students like to use Dreambox learning. And we know that the more time students spend on Dreambox, the more they will progress academically. And then the third thing is, we don’t talk about this a lot, but Dreambox was built by teachers for teachers. We pulled nationally board certified teachers out of the classroom. We paired them with engineers and we asked them to build something

that they would be willing to use in their own classroom. So it was built by teachers for teachers. And so we brought the best practice in to shape our product and our product evolution. And that continues, that kind of partnership and that reverence. I think last year we asked, I think there were 45% of people at Dreambox used to be former educators. I mean, think about that 45%. So we’re really trying to issue in a new paradigm, but issue it based on what the best teacher in the best

circumstance with the best resources might be able to achieve with her students. So what do you do to help teacher teams use Dreambox effectively at school? So that’s evolved over time. In the beginning, we were so focused on the software as a, you know, we had limited resources and we had to just focus in order to build something that was top notch product. And then over time, we had teachers say, we need help to demystify what’s

happening in Dreambox learning. We need help to make sure that we understand the use cases. We need help to understand how to use it to complement what we’re doing with our core technology. And over time, we’ve added capabilities. So now we have professional development that’s bundled in to make sure that every teacher in every learning community understands what we’ve learned over the course of the last nine years. They don’t have to make the same mistakes. We can share with them

best practices. We also have expanded our data and our reporting capabilities so that a teacher in a classroom can get insights about an individual student or groups of students that she might cluster together or indeed across a whole district. And then finally, we’ve added some capabilities like My Flex PD, which is job embedded teacher professional development that does include implementation advice but goes beyond that to help them with

how to manage a blended learning classroom. And it’s PD that will give them insight about what lessons students are working on. And they can actually get insight into what lessons a student is working on, where they’re getting stuck, and they can use that to inform their live instruction. So we really are focused on this balance and this relationship and this harmony between the live instruction and what happens in the software. It must be a little bit frustrating to look at your

data sets and see examples where you know the products not being used much or effectively and results aren’t nearly as good as the cases where you have adequate good use, good use of training, right? You must be able to see that data. Oh, we see that. We see that as a great opportunity. And the reason why it’s a great opportunity is, you know, people are rational. Teachers are rational. They don’t have much time. And if you show them what’s happening in classrooms

where it’s really working well, and then you show them what’s happening in classroom where it’s not implemented well, all you do is you tell them what they have to do to get their kids to be successful. I mean, if you assume that teachers want all their kids to be successful and you can be an agent to help them achieve that, then we share the data because it’s actionable. So if they see in teacher John’s class that they’re using Dreambox, you know, 45 minutes to an hour a week,

and they’re completing five lessons a week, and they’re seeing great student progression, and they’re seeing 60% higher gains than for students who are not using Dreambox. And then you look at teacher Mary’s class, and she’s only using it 15 minutes a week. If you pull teacher Mary in and you show her teacher John’s results, my guess is, and our experience is she changes it because she knows she’s not murdering her kids. She knows she’s not wasting her time. And she knows that she’s

going to get a return for her kids when she puts them on Dreambox. This is probably what you would describe as actionable insight. Exactly what. So we conduct impact reviews with all of our customers and we share their activity data. We share their usage data. We tell them how many kids are in the green zone of an hour a week or five lessons a week, and how many are on the cusp, and how many are not. And what we find is that is the nature of our partnership. We show them where they’re doing well.

We show them where they can do better. It’s formative in nature. It’s literally formative assessment that inspires difference in behavior. Yeah. In the last hour, we were on the phone with two amazing educators and they described using your data in professional learning communities. Yeah. And how important that was for them. Yes. And we love that. We have a version of that in what we call Dreambox Nation, where we invite educators to come in and share their experiences

with each other so we can kind of fold in the background and they can talk to each other. I struggle with this. What are your techniques for that? So that’s kind of an Uber PLC. But what we know that’s happening in various learning communities is that they take the data, they share the data, and they share best practices within a school building or within a district. And that’s how you scale what works. You have a bunch of really interesting investors,

some names that people will recognize, Reed Hastings and GSB, Kleiner Perkins, Turtle Growth Fund, Powell, and then last year, the Rise Fund. You’ve now raised a lot of money. I’d love to talk about the path forward, but let’s first start by talking about the fact that this is a group of people that are committed to the sector and take a long view. Those seem like those are important differences when you compare yourself to other

folks in the space. I think it’s an important success factor when you look at our progression. So just a minor amendment. We didn’t have Kleiner Perkins, but we did have John Doris Personal Family Foundation as an investor before the Rise Fund. When I spoke to our earlier investors, I had the benefit of having made most mistakes. I could have made it all those companies. You rattled off in the beginning. And one thing I knew is that traction takes time in K through 12.

And in order for us to build a Class A product we needed that would feed the nimble intelligent engine. We had to build every lesson. And so we didn’t build lessons in fractions. We build lessons at the sub-objective level so we could feed more nuanced data into the intelligent and adaptive engine. And so we build our lessons with focus on measurement or proportionality or decimals, etc. So when a child is not succeeding in fraction, we can ascertain with high fidelity why they are

not succeeding in fractions. We can direct their lesson pathway based on what we know they need. And so we didn’t have an inventory of questions that we could just go buy in the marketplace because it wasn’t built typically at the sub-objective level. So we knew we had to do that. That took time. We wanted to get really great teachers to author that. That took time. And we had to build the virtual manipulatives so that we could build the engaging experience around that. And early on

when I got here, I said I need five years and I need $48 million. And if you’re willing to do that, I will step off of Blackboard and I will come to Dreambox Learning. If you’re looking for a big return and you want to just, you know, get great profit and move on, then you’re probably, I’m not your CEO. And I had a group of patient investors who understood that we had to incubate success very intentionally in order for Dreambox to grow and thrive. And I’m very grateful to those

early investors because they gave me the time and the capital to attract the best minds and the best hearts to this work. And because we have such a high caliber team, that is why we have such a high caliber product. So now you have some money in the bank, what’s on the product roadmap? What would you like to get better at in the next three years? So there’s great opportunity, I think. So with the Rise Fund investment, there are things that we had to put on the back burner that now we can think about doing.

So there wasn’t a month that didn’t go by before the Rise Fund investment where I didn’t have some foreign country who saw the promise and the capability of Dreambox, say we won Dreambox in X country. And we didn’t have the operational capability and we didn’t have the leadership and we had to say no. We also have beta versions of our product in different disciplines and we weren’t able to invest in that because we didn’t have the capital and we didn’t have the breadth of operation to do that. That’s also a possibility.

We know that we are a software company and we’re collecting a lot of data about how kids are thinking and how they’re responding to each lesson. And so now with over three million kids on the system, we can leverage machine learning and big data to make our lessons even better and more nuanced and perhaps be able to drive competency with less time on the system. So I think there’s a whole area around efficacy and driving better results with intentional use of data that will bring high fidelity innovation to the intelligent adaptive engine that we’ve already created. And there’s a specific area around formative assessment, around predictive insights so that

imagine a situation, Tom, where we could look at a group of 30 kids and we could look at them in the beginning of the school year and we could tell the teacher who is on track for end of year success who is in jeopardy of not achieving end of year success and who really needs some serious remediation and is unlikely to achieve end of year success. But more importantly, what to do about it. So if we could use a sign focus and the intelligent adaptive engine to customize a success path for the end of the year

that could inform the teacher in the classroom what to do with her marginal 10 minutes or one hour of time with individual students or groups of students in a formative model, huge impact on student success, huge impact on confidence. And so we have the capability now to predict with high fidelity which kids are on track for end of year success and which ones are not. And more importantly, what to do about it. The third area, the fourth area

that we are exploring is how can we better serve the adult learning guardians. So we know that teachers are always going to be one of the most important influencers in student success. We also know, especially in the grade school environment, that we are cultivating generalists when you take a look at teacher preparation programs. Well, increasingly over time, if we want specialist skills in the classroom, then we have to take a look at teacher

professional development. And we are committed to expanding our professional development options to make sure that not only can we help support teachers be successful in Dreambox, but we can bring best practices about blended healthy vibrant blended learning

environments so that they can have a picture of what excellence is and emulate it. We need to do that especially in elementary schools. And then the final thing I’ll say is that it’s really important for Dreambox learning to think about learning empirically. So while we focus on mathematics and we are focused on early learners, we know that the science of learning

is very close to our philosophy and our approach. And if we can extend what we’ve learned about the science of learning, not only to teachers and learning guardians, but think about the result learners, think about all the kids in college or community college that never learned fractions, that are spending a lot of money in remedial courses for which they get zero credit

for years before they get to their core area of academic focus. What if, and think about the debt burden that results from that, we have an opportunity to take our learning about learning, our knowledge about how learning happens to try to tackle that if we so choose.

So I could continue to go on and on about possibilities for intelligent adaptive technology as a leader. My biggest challenge is focus. Now that we have the capital to do many, many things, we have to have the discipline to focus on the right thing that can have the biggest impact for the most, for the largest number of kids. Let’s close by squinting into the crystal ball and talking a little bit about future learning.

Both of us, hate standardized tests and what we’re doing to kids. We appreciate the instinct, right? We both want to add measurement to the system. I think we’re both excited about the fact that we’ve added so much formative data to the system since we both started this 25 years ago.

How might we use formative better in the future? So what we know about how the brain learns is that if we can provide feedback, immediate feedback, and we can do it dynamically, that we will create new insights that will impact

learners’ understanding of what they’re studying and what they’re trying to achieve. If we wait even a day, a week, in some cases, months or a year before we give them feedback and it’s in the rearview mirror, it doesn’t impact their learning trajectory as powerfully. And so I don’t think there’s a choice. We have to move toward formative models if we want to unlock learning potential. There’s not a choice. We have to move toward formative models if we want to help learning guardians teach more effectively.

And there’s no choice. We have to move toward formative models if we’re committed to cultivating competence as well as competence in learning. Learning should be fun. It shouldn’t be drudgery. It shouldn’t be about identifying winners and losers. We have to create learning environments that give kids credit for their last victory and don’t label them as slow, on target, or advanced. We have to move toward formative models. And now that we have these nimble systems of learning,

we call it intelligent adaptive learning, we now have the ability to scale learning on technology in ways that facilitate and support formative models. So that’s going to happen. We want to be a big part of that.

I feel it’s inevitable and it is the core of my hope for the future of learning. I’d love to close with a few thoughts on leadership. Yeah, you know, you you’re unfortunately one of the few African-American women leading a an important company in America. What have you learned, I guess, about yourself and about

building an impact organization that you can share? So when I think about leadership through the lens of diversity, I think about two things. We have to figure out ways to bring more students of color

to the table and make sure that they see their spark and make sure that we cultivate their spark to be stronger. There’s no doubt about that. A lot of people say they’re doing that. But the other thing that we have to do is make sure that we highlight hidden figures. So do you remember the picture of the NASA

essential room when we sent a man to the moon? Yeah. And there are a lot of white coats in there. A lot of guys in there. I think there was one woman in there. But recently there was a movie called Hidden Figures. Those are great flicks. It’s a great flick, right? It’s amazing, yeah.

And all these women of color who were really instrumental in getting the first man to the moon were not part of our history, were not part of our consciousness. And it leaves the impression to young girls of color that they don’t belong in that control center. So while it’s really important for us to get more kids of color to the table, it’s equally important to celebrate those that are already there who still may be hidden.

And so when I think about African American women, for example, that are trying to change the course of history, I think about people like the founder of Black Girls Code, right? Kimberly Bryant. People should know about Kimberly Bryant. People should know about Black Girls Code. And if we did a better job of highlighting the hidden figures, people like me wouldn’t feel like such an anomaly. It’s really important to me that young kids of all backgrounds

see themselves in teachers in the classroom. We know there’s research that says when kids of color see teachers of color, they’re 15% more likely to go to college. Incontrovertible. It matters. Showing up matters. So we have to do it from the teacher, scientists, innovators, entrepreneurs. When you think about a young man in a hoodie, who is white, what comes to mind? Maybe Mark Zuckerberg, you know, one of these guys that are

running a technology company right here in Seattle. When you think about a young gentleman in a hoodie who’s African American, does the same image come to mind? For most Americans, sadly, the answer is no. But why not? It’s because we’re not doing a good enough job highlighting the hidden figures so that young men and women of color see people like them in a diverse array of careers, having impact in society. And one of the things that’s most important to me is when I think about

some of the biggest challenges that we face in our future, in our shared future, I think about global climate change, I think about race relations, I think about a lot of things that are big problems that we need everybody at the table to solve. And if we don’t have people of color at the table locked arms with people from the majority, then we’re not going to solve problems together. And we’re going to have people who live in communities who are not going to see themselves

as people of agency and innovators and problem solvers who can help to pull their communities up and forward. And so the beginning part of this is education. The beginning part of this is unlocking learning potential. The beginning part of this is cultivating resiliency among young learners so that they don’t fear struggle. They’re challenged and motivated by struggle because they’re confident that they’re going to get to the other side of it. I mean, I think that so I’m a,

I read a lot of Brian Stevenson, I don’t know if you know him, social justice, and he has a phrase that he is that sticks with me. And he says proximity is the pathway to deeper understanding. And deeper understanding is a pathway to empathy. And I think what we lack so much right now in current society is empathy. And it’s because we’re not proximate to each other. That’s why it’s really important that public schools succeed, I believe, because it is one place where a lot of

different people from different backgrounds come together still in America, even if where they live is very homogeneous or even where they pray is homogeneous. Maybe where they work and where they learn doesn’t have to be so homogeneous. And if we can cultivate proximity, we can cultivate deeper understanding. And if we can cultivate deeper understanding, we’re going to have a kinder, gentler, more empathetic world for all of us to share and thrive in.

Thanks, Jesse. Thank you, Tom. A big thanks to Jesse for joining us for today’s episode. And for all the work that her and the entire Dreambox team are doing to serve math learners. That’s it for today, listeners. But before you go, don’t forget to rate and review today’s episode. We love seeing your feedback and it helps us get better. Yes. And make sure you also hit subscribe so you don’t miss out on any upcoming interviews. For the Getting Smart podcast, this is Jessica

and Caroline signing off.