Adaptive Learning and the Future of Education: A conversation with DreamBox Learning President and CEO Jessie Woolley-Wilson

As both a tech investor and a citizen who believes that our current pedagogical methods are in profound need of rethinking and reform, I’m bullish on the education technology space. It’s a huge, dynamic market and a meaningful sector on which to focus one’s attention. So, when my old friend Reed Hastings, CEO of Netflix, asked me to join him on the board of directors of DreamBox Learning, an edtech company, I was intrigued and decided to do some homework (so to speak).

I connected with Rocketship Schools, pioneer in the charter school movement, and early adopters of DreamBox. Rocketship went into East San Jose and revolutionized failing school systems with new methodologies, different teachers, and different approaches. I visited a school in East San Jose that had been one of the bottom five schools in the district. Now, they are one of the top five schools.

DreamBox uses a very different learning model than what I grew up with, where Mr. Smith or Mrs. Jones makes you sit in a seat for eight hours and trundle through the various subjects. Instead, DreamBox employs an “adaptive learning model,” which, enabled by technology, adjusts the very content of the pedagogy to the needs of individual students.

Rather than go on, though, I thought it might be more enlightening to go straight to the source. What follows is a conversation between myself and DreamBox’s President and CEO Jessie Woolley-Wilson.


Paul Holland:  So tell us about DreamBox. What problem are you trying to address?

Jessie Woolley-Wilson:  DreamBox is the company that pioneered Intelligent Adaptive Learning in 2006. Our mission is to reimagine learning so that regardless of where a child is in their learning path, they get a personal and relevant learning experience that meets them exactly where they are at in their development.

Now, that’s not easy to achieve, but it’s also not too hard. From the start, we had research that indicated that if you could personalize learning and keep kids in their proper learning zone, they would learn faster and more efficiently.

Today, we have over two million kids in our system. We do business in schools and districts in every state, as well as the District of Columbia, and all throughout Canada. We have over 80,000 teachers on our system, and it’s a K-8 supplemental curriculum.

That’s a meaningful footprint. And we are scaling nicely selling to the institutional market. We believe that we’re getting some traction because our solution is engaging and effective, as demonstrated by a recent Harvard University study. Both students and teachers find it engaging, which explains why educators are so confident about recommending that students spend more time on DreamBox.

PH:  Can you walk us through adaptive learning, ideal learning zones, and what this all looks like in practice?

JWW:  One of the challenges we face is that when other companies say that they’re adaptive, it conjures different meanings in the minds of buyers than what we mean. Most of the time, when an education company say they’re “adaptive,” they’re adapting pace and place. They don’t adapt the content.

I’ll give you an example of how DreamBox adapts the content. Let’s say, you and I are second graders, your math skills are better than mine, and DreamBox is trying to ascertain whether or not the two of us know how to group numbers effectively.

DreamBox might say, “Use the math rack to build the number 37.” And you say, “I know how to do that. I have to create some tens, create a five and then take two singles over on a math rack.” And in four or five moves, you build three 10s. You take a five, you build a five, and you take two singles over and you build the 37.

You don’t ask for help. You get it right the first time, not on the third time, and you do it with alacrity. You do it with speed and accuracy.

I, on the other hand, take 37 individual beads and move them over. So, we both technically got to 37 and answered the question correctly. But you can tell by the way we used our strategies to solve the problem that your understanding of numbers are at a very different place than mine.

So, in a typical adaptive program, because we both got it right, we would both progress to the next level or to the next lesson. And when I progress to the next lesson, because I’m not in the same place of proficiency as you, I’ll get frustrated. Maybe I’ll start to believe over time, because I’m frustrated, that I can’t learn math.

You, on the other hand, if held back to my level, might get bored really quickly.

PH:  I’m flattered that you’ve read my memoirs. [Laughter.]

JWW:  So, what most companies say when they’re “adaptive” is that they are moving kids through a specified curriculum, and some kids get there earlier, and some get there later. That would never happen in DreamBox Learning.

When DreamBox saw that I was not grouping numbers at all, it would pull me out of the lesson before I got frustrated. It would take me earlier into the lesson, reintroduce me to effective grouping strategies, and then give me a new problem and a new opportunity to be successful. And while I’m doing that, you’re being catapulted forward.

And it might be the case that DreamBox has, say, 50 lessons on effective grouping strategies for second graders. You, because of your level of proficiency, might only have to do ten of them in order to progress to the next level in mathematics. I, on the other hand, might have to do all 50 to get to the same level of proficiency.

DreamBox analyzes 50,000 data points collected and analyzed with the platform per student per hour, which helps us understand how students are thinking, what strategies they’re using to solve problems, and how closely and efficiently they are solving problems. So, we are actually adapting the content.

DreamBox’s distinguishing characteristic is that we adapt both within the lesson and between the lesson, and no other adaptive provider is doing that. They’re only deciding when you’re ready to move on to the next level – adapting pace and place – but they’re not adapting pedagogy in real-time as the student is actively thinking. DreamBox does.

PH:  I’ve got a story to back that up. In the case of that school I visited in East San Jose – which went from bottom five to top five – they were able to teach more kids with about 20 percent fewer personnel. How? They had a large computer lab.

When you think of a computer lab, you think of doing rote number addition or early coding. But in this lab the kids would spend a significant part of their day, perhaps two hours, working on various adaptive programs like DreamBox. So when they sit down to begin to work on their math assignment, rather than studying exactly what Johnny and Susie are studying on either side of them, they’re working on their own customized adaptive program, their own rich individualized curriculum, in a group setting. And then they go back into the more traditional classroom, and work from textbooks and other traditional materials.

Those are the places where I think DreamBox has fit in the best, and really become the all-star of learning styles for the kids and teachers.

JWW:  What I’d add to that is, the vast majority of our users use what we call a rotational model. Imagine, for a moment, the world’s best teacher has just been assigned to work with 30 kids in the classroom in a place like San Jose. How does that teacher know what Jessie needs and what Paul needs when Jessie is developing as a mathematician at a different rate than Paul?

So, she has to make a decision about how to deliver her live instruction. And what we enable learning guardians to do is to break that classroom up into, say, groups based on students’ prior knowledge of the day’s lesson.

So, she takes the on-grade-level group first. She has data from robust reports in DreamBox that give her a sense of what these six or seven kids are struggling with, where they’re excelling, and with what concepts they need reinforcement. And she can modify, on demand, her live instruction based on what that group needs.

Twenty minutes later, she rotates to the group of students who already understand the day’s lesson. She gets reports that show this group has mastered all the things that she had planned for the day, and they’re ready for the next level of content. So, she’s going to get them working earlier on something they aren’t scheduled to get in the regimented curriculum of the district for another two weeks. But she knows that they’re ready for it because she has data that shows that they’ve already learned the material in DreamBox and are moving well toward proficiency. So the instructor can modify her live instruction on the fly based on the data she gets from DreamBox.

And in the next twenty minutes she turns to the  students who don’t have any prior knowledge about today’s lesson. Perhaps they need significant intervention. With DreamBox, she can now give them a much more personalized learning experience, providing assistance where and when they need it. So their technology is personalized and their live instruction is personalized.

When children are in DreamBox, they’re architecting their own learning path based on what they demonstrate they know.

Jessie remembers her favorite teacher, Sister Saint Kevin.

PH:  We went through a period a couple years ago where everything was going to move online, and the traditional educational system was going to collapse as all the effort and all the energy went into MOOCs and new platforms like them. And then, of course, the efficacy wasn’t quite there.

What’s your commentary on the ebbs and flows of technology for edtech more generally?

JWW:  While we don’t talk about it a lot at DreamBox, one of the things that distinguishes us is the intentional engagement that we built to make sure that there were intrinsic rewards, and we made sure that there was a pull toward the technology. Kids actually want to use it. We have countless stories of kids waking their parents up at 6:00 a.m. and saying, “Can I work on DreamBox before I go to class?”

One of the things the MOOCs movement missed was the importance of engagement. I mean, you have to have classes that are actually enjoyable whether they’re online or not. The MOOCs movement underestimated the importance of being intentional about how to engage students so that they actually want to spend a marginal hour of their time on an online course.

Second, the promise of MOOCs was that you could imagine it would be great to have a great professor you might have had at, say, Stanford reach people globally. “Wow,” you might say, “if we could have students across the world have access to Professor Jones, with his great lectures, his brilliant mind, etc. – imagine the possibilities!”

The thing about MOOCs is that you can scale the great professors really well globally, but you will also scale the mediocre and the bad professors, too. One of the questions I always had about MOOCs was, How do you know that you’re scaling the best of the best? Where are the controls in place to make sure the experiences that we are scaling intentionally are the best experiences for the learner?

And I think that in their quest to get as much volume out as quickly as possible, they did not focus on quality and make sure that they replicated the things that worked best, that were the most engaging and that proved to be the most efficacious. It’s no wonder the abandon rate of MOOCs is very high, even from prestigious universities. A lot of people who begin their course online don’t complete it, and it gets back to that engagement piece.

So, I think the lesson is that we have to go beyond curriculum. We have to go beyond summative assessments. We have to think more experientially about learning. We have to figure out a way to encourage learners to lean into learning, even when it’s hard, because the experience is so compelling.

PH:  Let’s take a step back and talk about the national stage. We’re going to have a new Secretary of Education soon. What would you recommend for her?

JWW:  First, I hope the next Secretary of Education figures out a way to de-risk innovation in schools. We have to protect the innovators. Through the pursuit of innovation, we’re going to discover things that work better and things that work less well. But we have to press forward.

Second, in the wake of the recent presidential election, we need to have a Secretary of Education who is going to make it a priority to unlock the learning potential of every child, regardless of race, gender, zip code, culture, or religious background.

It’s not okay for us to allow kids to languish. And not just because we have a moral obligation to every child. It’s in our national interest to make sure that we unlock the learning potential of every child and make sure that learning environments are conducive and open.

We’ve all heard the recent reports about students coming in with white power signs and intimidating minorities in fifth grade. We need leadership around this to make sure that the learning environment is an environment that’s conducive to excellence and that is welcoming to all learners. That’s very important to me personally.

Third, I’m hoping that the Secretary of Education figures out a way to make it easier for education buyers to discern what works in what context and why, so that when the education buyer decides to purchase something like DreamBox, they understand what the success requirements are for scaling that technology in the classroom.

Right now, teachers and educators have insufficient time, they don’t have the expertise, and frankly, they don’t have any incentives to make sure that there is enough pre-purchase evaluation of solutions and post-purchase validation of solutions. They just don’t have the capacity to do it.

I’m hoping that the new Secretary of Education figures out a way to showcase the things that are working and to provide context about what the success criteria were that went into making it work for a given school or district.


Paul Holland is General Partner at Foundation Capital, and sits on DreamBox Learning’s board of directors. Paul is a longtime investor in education technology. His investment in Chegg (CHGG), a student-first digital learning platform, led to one of the few IPOs in the edtech space. Paul received his MBA from UC Berkeley, MA from University of Virginia, and BS from James Madison University. He has guest lectured on entrepreneurship at Stanford, Harvard, Columbia, Dartmouth, MIT, and James Madison University. 

Jessie Woolley-Wilson is Chair, President, and CEO of DreamBox Learning, Inc. Prior to DreamBox, she was President of Blackboard, Inc.’s K-12 Group and before that President of LeapFrog SchoolHouse. She is a board member of the International Association for K-12 Online Learning, Camelot Education, IslandWood, Seattle Venture Partners International, and the Woodrow Wilson Foundation. Jessie has an MBA from Harvard Business School and a BA in English from the University of Virginia.