It’s hard to imagine many students getting excited about math, but CEO Jessie Woolley-Wilson of DreamBox Learning, a Bellevue-based digital education company, swears it’s not only possible, but in some school districts, teachers actually reward their students with the subject.

“We believe there are a lot of kids who are not doing well because we’re not teaching them in a way they need to learn,” says Woolley-Wilson.

DreamBox uses intelligent adaptive technology to customize a math curriculum specific to each student, maintaining just the right amount of difficulty and understanding. The company is now in 48 states, the District of Columbia and three Canadian provinces. And the demand is only growing.

In 2011 the Bellevue school district launched its own DreamBox pilot program. The following school year it was adopted for students in kindergarten through third grade, and has since been expanded through fifth.

“Think about the best teacher you ever had in your life. How is that teacher going to prioritize and personalize for a [classroom] of 30 kids instantaneously?” asks Woolley-Wilson. “At DreamBox we know there are a lot of different ways to solve a problem, but it’s how you solve it that gives you insight into how ready that kid is for a certain level of instruction.”

Unlike other tech education companies that prioritize entertainment, Dreambox – started in 2006 by Lou Gray and former Microsoft Executive Ben Slivka – measures how students respond to a question, to assess their understanding of a topic. Using games illustrated by jazzy characters and a chirpy dialogue, DreamBox takes a sort of “choose your own adventure” route to learning.

Woolley-Wilson notes ballooning class sizes, alarmist headlines about the U.S. lagging behind other countries in math and science, and increasingly technology-infused lifestyles. DreamBox, she says, is meeting the challenges and demands of a new educational landscape.

“If you think about kids these days…the only time they don’t have technology is when they go to school. Kids have changed expectations and parents have changed expectations,” says Woolley-Wilson. “They want to make sure Johnny and Sally are ready not just to survive the next century but to drive it and thrive in it.”

Depending on a students’ math proficiency, programming leads them through a maze of games, pausing to help those who need more attention and moving on to later lesson plans for those with a better grasp. Not only does it offer a customized, version of learning, says Woolley-Wilson, but it also instills in students a set of critical thinking skills, that will serve them well beyond their K-12 years.

“Most educational technology shows you, ‘here’s how you subtract fractions using a common denominator, now go do it.’ Kids don’t actually have to think. That’s part of the problem,” explains Tim Hudson, PhD, curriculum director for the company and a former high school math teacher. “[Under that model] we’re cultivating a learned helplessness.”DreamBox launches students into an activity with limited instructions, forcing them to immediately begin interacting with their curriculum. Under a lesson plan on subtracting fractions, Hudson demonstrates using his son’s DreamBox portfolio by dragging blocks to the bottom of the screen.

Woolley-Wilson’s own route to DreamBox wasn’t what you might expect. Her parents are immigrants from Haiti, having come to the country only with their “faith, family and education,” she says. The importance of academics was instilled in her from a young age and Woolley-Wilson often volunteered her time as a tutor.

After majoring in English at the University of Virginia, she went on to get her MBA from Harvard University. She worked for Chase Manhattan Bank and American Express before a colleague encouraged her to apply her passion for education at Kaplan. Woolley-Wilson followed it with positions at collegeboard.com and LeapFrog Learning. In 2010 she joined DreamBox, soon after the company was acquired by Netflix CEO Reed Hastings and the nonprofit venture capital firm Charter School Growth Fund.

Woolley-Wilson admits there are skeptics. She cautions against too much screen-time for kids, and says program use should be gradually increased.

“I can’t imagine kids 24/7 in front of the screen, but I do see kids leveraging technology to optimize their learning experience,” she says. “Let’s not underestimate what kids can do. Kids are already consuming technology. The question is what technology they are consuming, and is it an engaged, fruitful, benevolent learning experience.”

That “sweet spot” of learning, as she calls it where students are both confident and challenged by their curriculum, is in part thanks to DreamBox’ partnerships. Instead of solely using software engineers to develop programming, the company recruits teachers to share their input.

“We’re compressing the time between that instructional moment and the epiphany. Now we have technologies that can impact learning at the moment of instruction, in real time. That’s never happened before,” says Woolley-Wilson. “I believe we’re helping teachers return to the art of teaching.”