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A panel on leading successful, innovative organizations at the GeekWire Summit 2019 at the Hyatt Regency Seattle, Oct. 9, 2019. From left to right: Ana Mari Cauce, president of the University of Washington; DreamBox Learning president and CEO Jessie Woolley-Wilson and Marilyn Strickland, president and CEO of the Seattle Metropolitan Chamber of Commerce. (Photo by Dan DeLong for GeekWire)

To build successful, impactful businesses, leaders need to do more than just manage diversity goals.

“We try to see diversity as something to leverage, something that we want to lean into. It’s an asset,” said Jessie Woolley-Wilson, president and CEO of DreamBox Learning, a digital education enterprise based in Bellevue, Wash. It all ties into the bottom line.

“If we don’t have women or people of color at the table, will we build as empathetic a product?” she asked.

Woolley-Wilson shared her thoughts on innovative leadership strategies during a panel at the 2019 GeekWire Summit. She was joined by Ana Mari Cauce, president of the University of Washington, and Marilyn Strickland, president and CEO of the Seattle Metropolitan Chamber of Commerce. Strickland led the conversation.

That diversity, the speakers said, opens the door to productive conversations that push innovative products forwards.

“We like to be hard on ideas and soft on people, and that means you have to subordinate your ego,” Woolley-Wilson said. All of these factors play together. “If you don’t have a diverse setting, if you don’t have an ability to subordinate that ego, a good idea may never become a great idea.”

DreamBox Learning’s math curriculum serves 3 million students in North America in kindergarten to eighth-grade. Last year, the company raised $130 million in venture capital in 2018 to expand and grow its reach.

The panel also emphasized the importance of hiring employees who are resilient, creative problem solvers. The UW, said Cauce, is trying to prepare students for an ever-changing workforce and for careers that evolve and shift over time.

“If you’re going to be an innovator, if you’re going to be an entrepreneur, we know that the first failure and the second and third failures are a step toward success,” Cauce said.

“It’s not about preparing students for their first job,” she said. “It’s about preparing them for a life where they’re going to have a first, a second, a third.”

DreamBox is likewise focused on teaching kids not just what to learn, but more importantly how to learn.

“When you look at a kindergartner in the face, how do you know what to prepare them for?” Woolley-Wilson said. “We do know is that they have to be life-long learners, and we do know that they have to be critical thinkers… I look for nimble intelligence.”


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