DreamBox Architecting ‘Next’ For Education Sector Through Acquisition And Optimism

The art and science of dreaming have, by many accounts, been thrown off course due to the rapid shifts of a global pandemic. Education, like most sectors, proved relatively ill-equipped to handle a customer base (students and families) forced to leave their stores (schools) for relatively safe harbor within the confines of home. Learning was thrust into mandatory digital landscapes with little time to breathe, let alone prepare for the realities facing public education.

It appears few were prepared to embrace the dramatic changes with confidence and planning that went beyond “just save the patient” tactics. Maybe the remedy lies in finding individuals with outsider roots to settle the moment and recognize the needs of both students and parents. Perhaps it takes a little dreaming to configure a new and vibrant future, today.

Some education companies that were asked to fill in the gaps exposed by the pandemic had already developed data-driven learning solutions and could, if given the opportunity, dramatically and efficiently improve learning. The pandemic illuminated the success of these newer ideas, which are now compelling administrators to consider full-fledged adoption more seriously.

I recently had the privilege of spending some time with the CEO and founder of one of those companies, Jessie Woolley-Wilson of DreamBox Learning, a math and literacy platform that adapts to the individual needs of students. From our discussion, key factors emerged that centered on personalized learning and the advantages of partnerships that align with existing pedagogy, teacher buy-in, and equity. Woolley-Wilson, once considered an outsider, has carved out a legacy whereby optimism fuels this leader’s methodical and confident approach to now leading one of the industry’s budding giants.

Rod Berger: You recently acquired Reading Plus. Why the move towards ELA, and why now?

Jessie Woolley-Wilson: The move to multiple disciplines is not a new idea, we’ve been looking seriously for a year and a half and probably considered 100 assets.

We landed on Reading Plus because of three main reasons; cultural alignment, innovation with respect to eye movement and reading, and perhaps most importantly, efficacy.

Reading Plus, like DreamBox, was given the highest ESSA “Strong” rating by Johns Hopkins University in terms of efficacy, making DreamBox now the only ESSA ‘Strong’ solution for both math and literacy. It’s very important to me and DreamBox.

If we are serious about supporting learning guardians, both at home and in classrooms, then companies like DreamBox have to derisk the move to blended learning for educators. We have to make sure kids and teachers don’t feel like they are being martyred and that means we have to subject ourselves to independent third-party evaluators.

Berger: Do you think more leaders like yourself are thinking holistically and working collaboratively to change learners by committing to system wide changes?

Woolley-Wilson: I think that we are at an inflection point in the industry and that’s reflected in policy. Recent federal funding insisted that schools find solutions that actually work, which wasn’t the case even as recently as before the pandemic.

DreamBox felt it was our obligation, but we didn’t want to be viewed as a vendor, but rather as a partner who shares the risk. That means committing to student success as much as districts.

Part of being a partner is stepping into the risk and saying you don’t have to believe us and our published stories because we have committed to demonstrating efficacy, with SRI, Harvard University, and Johns Hopkins.

The overall point of this learning is to give the guardian in home-based or school-based environments, insights about where a child is so that they can support them in the best way possible. For a teacher, that means actionable knowledge about what’s happening with students to modify instruction, organize groups differently, customize homework, or specific conversations with students based on what the system is showing. What works for Robbie might not work for Raul or Justine – it’s about personalizing the learning experience.

Berger: How do acquisitions change DreamBox moving forward?

Woolley-Wilson: We could have continued as a single discipline solution – we have market acceptance, kids like using us, parents trust us, teachers feel they’re more successful with it.

We’re proud of that, but our goal is to serve as many children as possible and we can have a bigger impact if we have multiple disciplines.

When we made the platform free during the height of Covid-19 a lot of people gained exposure to DreamBox. We knew pragmatically that this would probably translate into a culling of solutions. Many people are fearful of that, but I’m not because we think that the culling will be driven by efficacy, student usage, and teacher endorsement.

From our inception, we never wanted to replace the teacher, just leverage technology to best support the live practice. When we say we collect 50,000 data points per student per hour and use the online manipulatives – they represent things that are not possible in a live classroom. So, in many respects, we are merely allowing the software to do what the software does and seeing things in 3D, mixed with conceptual understanding to make the role of the learning guardian more supported.

If we can delight and surprise the learner while supporting and guiding the learning guardian in the process, we feel like we have the secret sauce to support student progress toward proficiency, regardless of what zip code a student lives in or their starting condition in life.

Berger: How have providers historically addressed personalized learning and what can we anticipate as we look into the future?

Woolley-Wilson: There are stages to personalized learning.

In the old days, the first phase was personalized learning success and getting devices in the hands of every kid.

The second phase was to digitize flat learning. So, you take a workbook and you digitize it, but it’s essentially the same thing.

The third chapter was where we actually use technology to do different things. That’s the chapter where DreamBox was born.

Many solutions say that they’re adaptive because they adapt at the pace or place of learning, but we also adapt pedagogically. We look at how problems are being solved, understanding the feeder skills to the macro skills. We refer to ourselves as, “Intelligently Adaptive.”

DreamBox will adapt its pedagogy based on what students are doing and where they demonstrate mastery. We adapt in pace, place, and pedagogy. Nobody else does that. We were able to do that by growing slowly to build lessons at the sub-objective level. It allows us to know where students struggle and master in a nuanced way. We can change the content and lesson progression so that every student gets what they need when they need it.

That’s important because as a student, you never feel your lesson is too easy or too hard. You feel challenged yet encouraged. You feel a sense of agency and accomplishment, regardless of where you are on your learning path. It translates into kids who are willing to persist through challenges, toward proficiency. I’m excited about this because instruction and assessment are in harmony. Now students and learning guardians can truly individualize learning through the system information, the observations of teachers, and what students articulate about their understanding.

Berger: I can imagine as a superintendent it could be hard to experiment with smaller providers that don’t have the legacy of DreamBox. Do you see it that way?

Woolley-Wilson: There might be something to that, but I remember the days when capital didn’t even look at K 12, they only looked at higher education. Talent wouldn’t consider going into EdTech and if they did, they would only go into higher ed. All the while, a little company like DreamBox was doing amazing, innovative things that no one ever paid attention to. As an entrepreneur, I hope that other future innovations get funding and get listed by amazing talent with the heart and passion for this sector.

On the other hand, I know that right now, superintendents, district administrators, and even principals are under so much pressure to deal with the social and emotional learning side that they have to spend intentionally.

It’s a hard time for district administrators, but I do believe that companies need to derisk their solutions for buyers. Those who have a trusted brand and have proven effective in different use cases with different populations can definitely succeed. Right now, district administrators don’t have the luxury of 15 different solutions for many subsets.

Increasingly, there’s pressure on companies like DreamBox to make sure that we have something relevant that can adapt to different strategies, teaching modalities, and learning styles at the student level.

In a sense, the market caught up to us because they saw the impact we’ve had on student progression, the efficacy standards that are delighting students and increasing educators’ trust. It’s forcing them to get to know our solutions. We have gone from a nice to have to a must-have in many respects.

Berger: What are the things that leave you feeling optimistic about the education sector?

Woolley-Wilson: There are a couple of things that come to mind, the first being talent.

When I got into this field in the late 90s, people thought I had lost my mind when I told them I was leaving banking to go into EdTech. Why would anyone in their right mind leave banking to go into something in its infancy at the time?

Cut to today – we recently hired a former director of product and technology from Amazon, who left managing a billion-dollar business with many employment options, to come to DreamBox. When I asked her why she wanted to shift into EdTech, she remarked, “You’re going to see technology transform three different industries. Fintech, Healthtech and EdTech. I want to see the same transformation that I saw in e-commerce happen in EdTech, so we can democratize learning opportunities.” I told her she was a perfect fit. As we seamlessly integrate data and analytics into content, I am really hopeful about what we can do to create new approaches to learning that respect what we’ve discovered over the years about learning science.

A second factor, which is a consequence of the pandemic, is the ubiquitous availability of devices and broadband. There’s still the last mile to go, but we have to take advantage and provide something that actually works for students and helps their learning.

The third is practice for behavioral change. A recent report by EdTech analysts Tyton partners asked around 3,000 teachers how their teaching practice changed in the pandemic. 89% said that they used blended learning or EdTech solutions in their classroom and intended to continue to use them going forward.

The fourth is policy. My goal is to get to a place where policies are informed by practice. Funding policy now dictates you can’t spend until you find something that works. That’s great for kids, great for communities, and I would argue great for democracy. I’m very optimistic about that development.

Finally, there is innovation. Imagine if we could use our predictive machine learning and AI capabilities at DreamBox to anticipate what a child would struggle with in the future?

In the same way that e-commerce altered the landscape of retail and buying habits of consumers, EdTech is now perched on the precipice of similar growth inside education that reaches beyond physical devices. If technology has brought us so far, does the next step in progress rely on individuals or organizations with vision, passion, and purpose to take us forward into a new era of true equality and educational opportunity?

Can providers, like DreamBox, effectively play the role of partner to transform a system that has remained largely unchanged for decades? The answer may lie in finding the right providers with the wisdom of well-evaluated solutions to properly partner the change. Woolley-Wilson believes she and her team possess the mettle to forge ahead, confidently.

Woolley-Wilson concludes our conversation with an anecdote from a previous interview with Colin Powell in which she asked him what keeps him hopeful? He looked at her and said, “Jessie, our only choice is optimism.” He repeated it to make sure Woolley-Wilson heard it. “Our only choice is optimism.”

“I will never give up on the potential promise of children. Never,” adds Woolley-Wilson. “As long as I’m hopeful about the capabilities of kids, I remain hopeful about our future.”

Interviews have been edited and condensed for clarity.