Unlocking potential through education — Jessie Woolley-Wilson of Dreambox #WCW

Sharvari Johari
Oct 2 · 5 min read

Welcome to All Raise’s Women Crush Weekly (#WCW), a series where we highlight genius women who are funding or founding tech companies. Please come back to the All Raise Medium blog weekly to find a new profile of an awe-inspiring female VC or founder. We’re focusing on EdTech and our crush this week is Jessie Woolley-Wilson, CEO of Dreambox.

For Jessie Woolley-Wilson everything comes back to a passion for education. Jessie is a veteran of the education industry, having spent over 20 years at companies like Kaplan, LeapFrog SchoolHouse, Blackboard and now as CEO of DreamBox Learning. Throughout her career, Jessie has been driven by a singular belief that all children need and deserve high-quality learning opportunities, regardless of who they are or where they live. Jessie believes talent exists everywhere, but opportunity does not, and we must find ways to democratize education so that every child has access to the best learning environment possible.

DreamBox seeks to unlock learning potential for all kids through its online K-8 math program. The product is designed to learn with the learner, adjusting to each student’s unique learning needs and automatically offering kids the right lesson at the right time. Dreambox now supports over three million students and 130,000 teachers across all 50 states, Canada, and Mexico. Independent studies from Harvard University and SRI have demonstrated that DreamBox improves student achievement. With CEO Jessie Woolley-Wilson at its helm, DreamBox is empowering all kids to develop both a love and an understanding of math.

In September, our education technology month, I asked Jessie what led to her focus on education, and how this passion has guided her throughout her career.

Question: What role do you think new educational software companies, such as DreamBox, have on the future of education?

Answer: At DreamBox we are determined to build student confidence as we’re building competence in math. We don’t see technology as a replacement for teachers or, learning guardians, but as a complementary tool. We also believe to prepare kids for the future workforce, we need to teach them how to use technology. DreamBox does not just teach students math, the platform is designed to teach students how to learn and think critically about problem-solving. Just like there are multiple ways to solve a math problem, there are multiple ways to address challenges people face in the workforce. DreamBox is equipping students with these skills early on so that they can excel in whatever job or industry they chose.

Q: What prompted your passion for education?

A: My parents, including my father, who immigrated to this country from Haiti, were inspired by the teachings of Martin Luther King Jr. and Bobby Kennedy on the American ideal that with a great education came great opportunity. This influenced them to make a life for our family here. And while I did not pursue a career in education right away, my parents’ passion for education inspired me to volunteer as a tutor for children in Harlem. After working with these kids, I discovered the only thing that was different between me and them was that I had amazing parenting and access to a great education. This ignited my passion for unlocking learning potential for all kids — regardless of race, gender or zip code.

Q: How has your experience working in other educational companies helped you run DreamBox?

A: I like to think of my life in chapters. I am grateful for the opportunity to work at other educational companies because each experience (chapter) was an opportunity to learn, build community with other educational innovators and to grow from both successes and learning opportunities. These experiences also taught me how important it is that we best support our teachers and students with the right solutions that meet their needs. I believe the key is to reflect on each of these chapters and imagine new opportunities for the future.

Q: Was being a CEO always your dream job? if not, what was?

A: While I did not always plan to be a CEO of an edtech company, I knew that with a high-quality education, the support of my community and a willingness to learn — I could reach any goal. I originally thought I would grow a career in banking, but I later learned that banking did not fuel my passion. From that moment forward, I have always pursued job opportunities that I am truly excited about. Even when times get hard, if you have a passion for what you are doing, you can face any adversity. That is why I love working with the team at DreamBox — our team believes in the work we are doing together even when it is challenging.

Q: What is your favorite part of your job?

A: Every day I come to work excited about the opportunities at DreamBox. I’m blessed to work with a team of intelligent, mission-oriented innovators who are doing important work to help kids understand their full learning potential.

Q: What advice do you have for aspiring female entrepreneurs?

A: Work really hard and study really hard. Make the most of the educational opportunities you are given. My parents are my greatest inspirations. They reminded me of how fortunate I was to have access to some of the best educational opportunities this country had to offer. They encouraged me to capitalize on the advantages I’d been given and to build a meaningful life centered around family, service and learning.

Q: If you could have a conversation with your 18-year-old self, what advice would you give to her?
Answer: I would give myself three key pieces of advice. First, I would tell myself to follow my passions. When you follow your passions, you will feel more fulfilled, even when times get challenging. For me, that meant switching my industry focus to satisfy my passion for education and learning. Today, I like to ask potential hires at DreamBox about their passions when I interview them. If they don’t share our passion for unlocking learning potential for all kids and supporting learning guardians, then they are not the right fit for DreamBox.

Secondly, I would tell myself to surround myself, especially early on with what I call, “truth-tellers.” These are people who believe in you, support your aspirations, and are willing to risk your disappointment or anger to tell you the truth. This keeps us honest and humble so that we can continue to grow, learn and improve.

Finally, I would say prepare for luck. It’s important to study hard and work hard while learning from mistakes. The harder we study and work, the better prepared we are to act when luck presents itself.

All Raise

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