Season 1 : Episode 9

Education for All

Nov 2020 ∙ 00:25:30

Education for All

The global spread of COVID-19 has underscored the long-standing racial and socioeconomic inequalities across many industries and sectors. While education has long been thought of as the great equalizer, the relationship between poverty and educational disparities proves otherwise. In today’s episode, inspiring EdTech leader Jessie Woolley-Wilson shares how DreamBox and the EdTech industry are using technology to provide high-quality learning opportunities for all.

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The Girls in Tech Podcast is produced by Tote + Pears.
Music By: Adrian Dominic Walther

Featured In This Episode

Jessie Woolley-Wilson is President and CEO of DreamBox Learning®. Prior to joining DreamBox, Jessie held executive positions at multiple leading EdTech companies, including Blackboard, LeapFrog and Kaplan.

Jessie is a two-time recipient of EdTech Digest’s “EdTech Leadership Award” for her work in transformative innovation in education, and she has been named among the “Top 100 Influencers in EdTech.” Forbes placed her on its “Impact 15” list for being a disruptor in education, and The New York Times featured Jessie in its Corner Office column.

Regionally, Jessie has received many accolades, including Seattle Business Magazine’s Executive Excellence Award in the “CEO of the Year” category, GeekWire’s “Big Tech CEO of the Year” award, Puget Sound Business Journal’s “Women of Influence” and “Innovator of the Year” awards, and the Ernst & Young “Entrepreneur Of The Year®” award in the Pacific Northwest region.

She serves on several boards, including Rosetta Stone and the Western Governors University Board of Trustees. She has been a featured speaker at many events, including TEDx Rainier, SXSWedu, DENT, GeekWire Summit and the ASU GSV Summit.

Jessie holds an MBA from Harvard Business School and a BA from the University of Virginia.


Adriana Gascoigne (00:00):

I’m Adriana Gascoigne, founder of Girls in Tech. And this is The Girls in Tech Podcast, where we’re discussing the ways tech is always evolving and helping the world evolve too. Listen in, get inspired and learn how you can use your skills to create the change you want to see in the world. Here’s your host, Zuzy Martin-Aly.

Zuzy Martin-Aly (00:20):

There’s a company that will value you for you. There’s a tech job where your skillset and unique perspectives are appreciated. By inviting you to share the real you, the Girls in Tech Jobs Board helps you find that job so that you can take the next step in your career with confidence. Go to today. That’s

Jessie Woolley-Wilson (00:45):

When you help others, especially if they’re children — children are smart, kids know who believe in them — and if they see that you believe in them, especially when they don’t yet believe in themselves, transformation for their whole lives, one person, maybe one interaction, amazing power.

Zuzy Martin-Aly (01:06):

We all feel that the coronavirus has turned our lives upside down. And yes, for many of us, this is very true, but don’t let the sense of shared struggle fool you. It’s really not equal. The pandemic has disproportionately affected marginalized communities, placing them at even greater risk than before. This is especially true when schools were forced to turn to online learning — and inequalities and the education system became impossible to ignore. Many low-income students and families found themselves without the technology or support to navigate this new learning model.

Zuzy Martin-Aly (01:40):

And it is estimated that over 23 million children and youth may drop out or not even have access to school next year due to the pandemic’s economic impact alone. To help me understand the role that tech plays in creating equity in education, I’m so happy to be speaking with EdTech leader, Jessie Woolley-Wilson, president and CEO of DreamBox Learning.

Zuzy Martin-Aly (02:02):

Jessie is passionately committed to providing access to high-quality education to every child, regardless of where they live, where they come from or what they look like. Here’s my conversation with Jessie.

Zuzy Martin-Aly (02:15):

Thank you so much for being with us today. We are speaking about one of my favorite topics — education and technology, and how technology is shifting and addressing so many things that are important in the world of education. So, let’s get right into it. So, over 140 countries use DreamBox. Can you tell us a little bit about that journey and the scale of how many people and how many young lives you affect?

Jessie Woolley-Wilson (02:44):

So, right now DreamBox serves about 5 million kids and over 200,000 educators, and the bulk of our businesses in the domestic United States, Canada and Mexico, but we serve kids in about 140 countries. So anybody can go to and have access to the math curriculum. One of the reasons we’ve been able to have a broad footprint like that is because math is a universal language, and our approach is driven by gains.

Jessie Woolley-Wilson (03:15):

So, if it’s not language-dependent, and it’s basically gains and virtual manipulatives, it doesn’t actually matter what language you speak. And you can learn mathematics on DreamBox Learning. It might be more challenging if we were doing history or something else, but because math is a foundational skill and we’re focused on STEM skills — science, technology, engineering and mathematics — we think math competency and proficiency will enable all of those other disciplines, including reading.

Zuzy Martin-Aly (03:48):

Please, tell me more about DreamBox. What are you doing to drive access to high-quality educational activities?

Jessie Woolley-Wilson (03:55):

So at DreamBox, we try to create a technology that supported both the learner and the learning guardian to delight and surprise them so that they would enjoy the learning experience. And so, we created a new technology that we pioneered in 2006 called Intelligent Adaptive Learning. And what it does is it customizes the learning experience for every child dynamically, moment by moment, click by click, finger move by finger move through the technology.

Jessie Woolley-Wilson (04:31):

And the best teacher in the best resource environment could not do that at scale for the 25 or 30 kids that she’s responsible for. So, instead of seeing technology as something that can just automate current learning models, we see technology as a way to usher in new learning models. So, technology at DreamBox is designed to do things that only technology can do, personalize learning at scale dynamically.

Jessie Woolley-Wilson (05:02):

And technology is designed to serve the interests of both the learner and the learning guardian — be it teacher, tutor, parent, grandmom. We can’t go around the teacher. We have to equip the teacher with new tools to usher in a new kind of learning. And if we do it that way, we believe at DreamBox that technology will serve the interest of humanity instead of the other way around.

Zuzy Martin-Aly (05:29):

And you’ve said before that technology cannot replace teachers. How do teachers work with this adaptive learning technology, and how does it benefit the students? I’d love to hear an example of some school districts where it’s really working well.

Jessie Woolley-Wilson (05:46):

So, what I can tell you, let me tell you about how it works. So, if you and I were second-graders and the teacher was trying to figure out how well we could group numbers to solve problems, DreamBox might say, use the math rack — so a virtual platform on their iPad or on their desktop to build a number, say 37. So, let’s say your math skills are a little better than mine. So, you say, Oh, I want to build some tens. I’m going to build three tens. Then we’re going to build a five, then I’m going to take the last two beads and roll them over to make 37. And in four or five moves, you group numbers effectively. You do it very efficiently. You don’t ask for help, and you get it right.

Jessie Woolley-Wilson (06:28):

I, on the other hand, take 37 individual beads and I move them over one by one. So if the teacher is walking around the classroom and she sees that you got 37 right and I got 37 right, she might say, both of us should be advanced to the next lesson. But what DreamBox knows that she doesn’t yet know is that Jessie didn’t group numbers at all. Jessie didn’t demonstrate an understanding of how to group numbers and solve problems efficiently.

Jessie Woolley-Wilson (07:02):

So, what DreamBox would do is it would see that Jessie is not grouping at all. It would pull me out of the lesson before I got frustrated, 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. All this happens dynamically. DreamBox might look at you and say, “Wow, Zuzy, that’s so fast. Maybe of all the 30 problems that we have on grouping, she doesn’t have to do all 30 to be proficient. Maybe she only has to do seven. So I’ll give her a harder problem to demonstrate that she actually has command of this.”

Jessie Woolley-Wilson (07:41):

So this happens dynamically, moment by moment at scale because we developed a technology that doesn’t just look at, do you get the right answer? It looks at the strategies you’re using to solve the problem. And it customizes the pedagogy. It customizes the actual lesson you receive, not based on what’s next in the curriculum, but what’s based on what you had demonstrated you already understand deeply.

Jessie Woolley-Wilson (08:06):

So what it means is that the technology meets the child, every child, where they are, it customizes the learning experience for every child. So there’s no stigma. It’s not the slow kids in the back and the fast kids in the front. Every child has an individual learning path that’s based on what they need and they get exactly what they need when they need it.

Jessie Woolley-Wilson (08:27):

So, even the best teacher in the best-resourced school can’t do that at scale. This is why technology can do things that only technology can deliver. Mass customization at scale. And right now, when everybody was challenged with COVID, 100% forced online learning, the kids who were on DreamBox were ready. They already had that relationship. They already had that exposure to this next-generation learning. And even though it was still very hard — I mean, it’s very hard in COVID — they had a leg up.

Jessie Woolley-Wilson (09:00):

So, it’s very important to me and everybody at DreamBox that kids who get access and teachers who get access to these technologies are not just those in the wealthiest schools or the wealthiest homes. We want to make sure that every child, regardless of what ZIP code they happen to be living in has access to the best learning experiences so we can unlock their learning potential. And in doing so, unleash their human capabilities.

Zuzy Martin-Aly (09:26):

And that leads to my next question. I’d love for you to expand on that, the importance of unleashing human capability. Why is it so important to look at EdTech through this lens, through the lens of equity?

Jessie Woolley-Wilson (09:39):

So, there’s a lot of change that is happening in education. The concentration of poverty and the concentration of ethnicity in public schools is higher than it has been since Brown v. Board of Education. And so, if children do not have access to the same opportunities to grow and to thrive, then that has generational impact. Not only for themselves, but for their families and their communities. And it’s my personal opinion that in order for children to be the purveyors of solutions for themselves, their families, and their communities. We have to invest in them and help them build those skills.

Jessie Woolley-Wilson (10:22):

And what that promise is, is people will not come to do things for people in these communities or to people in these communities. People in these communities will actually be the solvers of the problems themselves. It’s about building confidence and competence through learning. And so we have to empower these communities because we know they’re disproportionately impacted by global climate change or COVID or health access, name it.

Jessie Woolley-Wilson (10:59):

And so, we need to make sure that they are prepared for an information-driven globalized economy, where the kinds of jobs they are going to be asked to do are going to be inextricably linked to their command of, and familiarity with technology.

Zuzy Martin-Aly (11:18):

I’m glad you’re explaining it this way because education and inequality has become more inflamed and more politicized that it’s hard for people to talk about the basic fact of giving a child the same right to education as anybody else. So let’s talk about hope, okay?

Jessie Woolley-Wilson (11:41):


Zuzy Martin-Aly (11:41):

What do you expect or hope for the future EdTech?

Jessie Woolley-Wilson (11:47):

So, what I hope is that we move intentionally to a place where technology is viewed as a tool, as something that serves both the student and the teacher, or what I say, the learner and the learning guardian. And while we believe that at DreamBox, I don’t think that’s consistent across EdTech. So there are different chapters of EdTech. The first chapter was how do we get everybody a computer? And we thought that was successful until we thought, well, what are they doing once they get the computer?

Jessie Woolley-Wilson (12:16):

And then we turned to activities and software curriculum. But what we did was we took a textbook and we digitized it. And we said, now you can do the same thing in the textbook online. That’s really not next-generation. The third chapter, which is the chapter we’re in, is about how do you personalize learning so that you do different things that only technology can enable?

Jessie Woolley-Wilson (12:39):

So, we’ve got to think very intentionally about how do we build capacity in districts and in homes. And instead of thinking about learning traditionally, that happens in a school-setting from eight o’clock in the morning to three o’clock in the afternoon, we have to start thinking about age, grade, and setting agnostic learning. We have to make sure that technology can enable a really enjoyable, engaging, and effective learning experience if part of it is at home and part of it is at school.

Jessie Woolley-Wilson (13:15):

So, I hope that the future of EdTech is an intentionally blended future, where we use technology to do the things that technology is best suited for, and we actually help learning guardians get time back so that they can spend more time with the art of learning, the art of teaching.

Zuzy Martin-Aly (13:35):

That is an inspiring hope for the future. And there are so many people like you working towards this. I have no doubt that we can get there really soon. I would love to talk to you about, how has it been to be a female leader in EdTech?

Jessie Woolley-Wilson (13:50):

So, technology is not led by women. And frankly, there are a lot of education technology companies that are still largely run by men, so there are obstacles for women. Access to capital is one option. So you go, you try to raise money. And if you are packaged the way I’m packaged — and people aren’t used to that — then you have a few more things you have to convince them of before you actually do the ask.

Jessie Woolley-Wilson (14:21):

The other thing is then, since there are so few people who have come before, how do you understand how you succeed in that environment? What rubric are investors using to evaluate where they invest? So, a lot of men have a lot of support and they’re very well prepared when they go in for that pitch meeting. They know how the game is played. They know what rubric they have. They know what they have to do.

Jessie Woolley-Wilson (14:47):

And if you’re a first time, you’re an immigrant, your first time and you don’t have anyone telling you what they went through, then you’re figuring it out on your own, and it takes longer to be successful. And so, one of the things that I’m very, very passionate about is trying to pay it forward, trying to share my experiences, trying to share what I did wrong so that women, in particular, don’t have to make the same mistakes that I did.

Jessie Woolley-Wilson (15:15):

And so, it’s really important to be in the game to show up, to be visible so that women who might not think that they can do it, can see that they can do it, and they’re worthy — they’re just as worthy as anybody else to go after the big idea.

Zuzy Martin-Aly (15:34):

And education seems like the absolute perfect industry to take transferable skills and go in this direction of EdTech. So how does one start going in that direction?

Jessie Woolley-Wilson (15:46):

So, for me, I started in banking and I tutored kids, and I thought, “Wow, this is fantastic. I could take my business skills and I could apply them to education while education is being transformed. And I might be able to have an impact in this world.” So, I would tell your audience that it’s never too late to follow your heart’s desire. And the things that you care deeply about are the things that you’re going to be willing to work for when it’s really, really hard and when the prospects of success are not high. But you’re still going to enjoy them because you care deeply about them. You’re passionate about them. And I was very passionate about education and educational access. So, that’s one thing.

Jessie Woolley-Wilson (16:29):

The second thing is to learn from other people, especially including other people who don’t look like you. There were a lot of people helped me — sponsors, mentors who were men or who were not diverse candidates and who saw something in me. And when they were informed where I couldn’t be, they advocated for me. And they sponsored me, and they created pathways for me. And what we have an obligation to do is to make sure that we keep the pathways open behind us and the doors don’t shut after we walk through them.

Jessie Woolley-Wilson (17:02):

The third thing I would say is be constantly learning. The things that I learned in business school that maybe helped me in banking, I had to reformulate them for an emerging industry called education that was being disrupted. And so, think about it. Healthcare is being disrupted, highly regulated, being disrupted by technology; financial services, FinTech being disruptive. There’s so many emerging industries that need people who know how to learn.

Jessie Woolley-Wilson (17:38):

So, it’s not necessarily the specific thing you learn, but that you’re an expert at remaking your skills over and over again, so as industries change and opportunities change, you can adapt with them and you can learn how to thrive in new environments because you’re curious, you’re adaptable and you can learn new things. You can demonstrate that you can learn new things.

Zuzy Martin-Aly (18:02):

So, for women listening who are a bit intimidated to go into this space, why is it so important for women to be involved in creating these new technologies?

Jessie Woolley-Wilson (18:10):

So, education is an environment that there are a lot of women who are leading — principals and district administrators — and their world is changing. And so, it’s really important for women who have a passion for education to embrace the new models that are emerging so that they can shape them instead of being overwhelmed by them. And if you get in early, then you’re going to be in a much stronger position to proactively shape them, to make sure they serve the interest of the kids that you’re in charge of.

Zuzy Martin-Aly (18:40):

You have the former U.S. Secretary of Education, Mr. Arne Duncan, on the DreamBox board. That’s wonderful. Can you talk a little bit about the importance of board members and what role they play on shaping an organization and why it’s important?

Jessie Woolley-Wilson (18:58):

I’ll say two things about boards. The first is that every woman in your audience should take time to form her own personal board of directors. These are people who have expertise in areas that they don’t have. These are people who have access to forums that they don’t have. And most importantly, these are people who believe in them and in their dreams. These are people who are going to support them when times get windy.

Jessie Woolley-Wilson (19:26):

Personal board of directors are invaluable resources to emerging women leaders. And I would encourage everyone to find people who are willing to advocate for you, and support you, and have courageous conversations about you when you’re not doing what you should be doing. So personal board of directors. And then the formal board of directors, most companies have boards that are formed with a mix of investors and independent board members that help them make their organization more successful.

Jessie Woolley-Wilson (20:00):

So oftentimes, boards are predominantly made up of people who have invested capital in, and then it’s complimented by people who are subject matter experts who can really give you nuanced insights about the industry and hopefully, about emerging trends in the industry. And Arne Duncan is that for DreamBox Learning. He was instrumental in helping district leaders understand and reshape the relationship with technology.

Jessie Woolley-Wilson (20:31):

And so, it’s great to have that innovator and somebody who cares so deeply about all kids. To hear secretary Duncan tell you stories about how his worldview has been shaped by proximity to all kinds of people from all kinds of backgrounds, it’s very easy to understand why he’s so passionate and why he’s so effective. So we’re very fortunate to have somebody who’s so prominent, but somebody who shares our values, who believes in the company mission, and is willing to have courageous conversations with us when he thinks we can do better for kids and teachers.

Zuzy Martin-Aly (21:08):

I absolutely love the advice you’ve given or the directive you’ve given us to create our own personal board of directors so much like Secretary Duncan, helping us in areas that we need help in expanding because no one’s perfect.

Jessie Woolley-Wilson (21:28):

No one’s perfect.

Zuzy Martin-Aly (21:28):

So there’s always going to be an area where you need that push to get to the next level. And just like you have for DreamBox, thank you for encouraging all of us to do that for ourselves. What roles or skills do you think are needed to get into this space? And also, if you could touch upon getting on a board.

Jessie Woolley-Wilson (21:50):

Yeah. Well, first on this space, so I went to the University of Virginia and I majored in English and I’m running a technology company. So sometimes people think that if you’re going to be in technology, you have to be an engineer. I want people to open their aperture and to think about all the things, all the skills, and all the activities that happen in technology companies. There’s marketing, there’s customer support, there’s engineering, there’s finance, there’s every possible function that exist in any company also exists in technology companies.

Jessie Woolley-Wilson (22:25):

And there’s so much to learn if you come to the technology industry. And so, sometimes we hear young girls on the system say, “I don’t want to be good at math because I don’t want to be an engineer.” Well, being good at math is going to open up a lot of opportunities, including, but not exclusive to being an engineer. It’s going to make you better at everything you do. Even if you’re interested in music, right now, music is composed with software programs. People aren’t writing treble on a graph in paper and pencil. They’re doing it on a Mac or some other device.

Jessie Woolley-Wilson (23:06):

So technology is infusing everything we do and redefining everything from communications to robotics, with a lot in between. And so, instead of thinking about it with some long-term activity in mind, we should just think about it as a life skill that’s going to make us successful in whatever pathway we choose from music to politics. Who among us isn’t going to say that people who understand social media and technology are not better positioned for success even in politics?

Jessie Woolley-Wilson (23:40):

There is no place you can hide from technology. And so, we should embrace it as a life skill, get proximate to it and make sure that we are confident in a technology environment.

Zuzy Martin-Aly (23:53):

Any final thoughts or inspiring words to share with the Girls in Tech audience?

Jessie Woolley-Wilson (24:00):

This is a thought I’d leave you with. And that is, see yourself as a learner, absolutely. Because as you learn more, you will adapt more and more opportunities will come to you. I want people to be ready for luck when it happens because everyone has a little luck, but we have to make sure we’re ready for it. So the first thing I would say is be ready for luck by committing yourself to becoming great at whatever it is you’re interested in.

Jessie Woolley-Wilson (24:28):

Align with your passion, infuse it with technology, and don’t be afraid of short-term [inaudible 00:00:24:35]. That’s the first step to getting it right. The second thing I would say is not only are you a learner, but you yourself are a learning guardian, who is it that you can help from a learning guardian point of view?

Jessie Woolley-Wilson (24:49):

Maybe it’s a young child, maybe it’s a peer, maybe it’s a sibling, maybe it’s people that you spend time within a community center, find a way to scale goodness, starting with yourself. What can you do to make the world better from the seat that you sit in? If all of us think about that, even if we all do one extra thing, imagine how many more extra things will get done. One person makes a difference.

Zuzy Martin-Aly (25:18):

Jessie, it has been such a great pleasure speaking with you. Thank you for being with us today.

Jessie Woolley-Wilson (25:24):

It’s been my pleasure and thank you.

Zuzy Martin-Aly (25:29):

Thank you for listening to today’s episode. The Girls in Tech podcast is a production of Tote and Pears. Were you inspired by what you heard today? Head over to to find more resources for starting and advancing a career in tech, including our jobs for it, and personal and professional development programs designed to help you excel. and be sure to tune in every other Tuesday for new episodes. See you next time.


The Girls in Tech Podcast is produced by Tote + Pears.
Music By: Adrian Dominic Walther

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