The 2015 Executive Excellence Awards: Jessie Woolley-Wilson

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Jessie Woolley-Wilson

Chair, President & CEO, DreamBox Learning

In her four years at DreamBox Learning, Jessie Woolley-Wilson has proven herself an evangelist for improving learning comprehension and has helped spread the company’s personalized instruction systems to classrooms throughout the United States and Canada. DreamBox Learning’s tutoring software decides the ideal next lesson to present, based on how a child responds to the most recent one, so each student’s experience is different for his or her needs.

DreamBox develops “adaptive learning” software and its CEO, a former banker, has had to do plenty of adapting, too. “I sit here as an English major with an economics and physics degree,” says Woolley-Wilson of her responsibility for leading the flourishing e-learning firm. Last year alone, she expanded her staff from 39 to 93. “If you can adapt [and] harness collective wisdom,” she says, “you can find the pathway to your goal.”

The company has adapted to change as well, embracing the rise of tablets such as the iPad, expanding curricula for middle-school students and adding Spanish language to its grade-school math programs. Woolley-Wilson is excited that today’s students are increasingly comfortable in a world where work and play are globally connected through technology.

All kids can succeed, she insists, with approaches and tools that are as diverse and flexible as the children themselves. “This notion that some kids can really learn and some can’t,” she asserts, “we’re disproving that every day.” 

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