Amid the swirling uncertainty of WNBA free agency, the Chicago Sky made a major addition this week — to their front office, not their roster.
The Sky hired Nadia Rawlinson for a newly created role of operating chairman. Rawlinson, 43, aims to establish a stronger base for the business aspects of the team as the WNBA continues to grow on and off the court.
“For so long, many WNBA teams have been just trying to survive,” Rawlinson said. “Especially from an operational standpoint, they were just trying to get through and make it. And now it’s time to thrive.”
Before Rawlinson’s hire, the Sky’s executive branch consisted of three people: CEO and President Adam Fox, chief financial officer Stephanie Hedrick and head of strategy Watchen Nyanue.
Principal owner Michael Alter and Fox began to discuss the concept of creating the operating chairman role in 2021. It wasn’t a concrete position, and the franchise never underwent an interview process. But last year when Alter met Rawlinson — who initially was interested in simply investing in the team — he quickly began to feel the Sky had found their new operating chairman.
Rawlinson brings a deep background in human resources, strategy and business development — as former chief people officer for Slack Technologies; as the former chief human resources officer for Live Nation Entertainment; and as a current consultant for venture capital firm Google Ventures. She currently serves on the board of directors for J. Crew, Vail Resorts and Save the Children and sits on the Stanford University Board of Trustees and the Harvard Business School Board of Dean’s Advisors.
To Alter, the experience paired with a deep love for Chicago, basketball and the empowerment of women’s sports made Rawlinson the correct fit.
“We thought, ‘If we find the right person, it would be great to do this,’ ” Alter said. “We didn’t do any formal search. It was really just a thought that we had. She’s absolutely the perfect person to be in this role.”
Rawlinson will oversee the development of the Sky’s strategic business initiatives, which includes establishing and growing corporate partnerships and increasing the organization’s civic engagement throughout the community.
Rawlinson and Alter highlighted two areas for immediate growth. The first is sports betting, which recently became a viable revenue outlet because of laws enacted in March. The second is the establishment of a media rights deal in 2025, which Alter believes is “way undervalued” under the current agreement with the WNBA.
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Alter believes Rawlinson’s expertise from the corporate sector will allow the Sky to increase revenue to compete more fervently in future free-agent markets while also providing benefits such as charter flights, which became a key topic for players this offseason.
“The biggest objective we all have is we need to grow revenue,” Alter said. “That’s how we pay players more money, which they badly deserve. And that’s how we afford the charter flights, which they also deserve. So those are all things we want to have. We need to be in a position to do that.
“One of the ways we do that is by bringing in incredibly talented people like Nadia, who could be working, making a lot more money somewhere in the corporate world but believes deeply in what we’re trying to build here.”
Alongside her role as operating chairman, Rawlinson also joins the Sky as a co-owner, with Alter remaining the principal owner. It isn’t her first venture into sports investment — during the pandemic, Rawlinson and her husband started a sports fund to invest minority stakes in minor-league baseball, lacrosse and hockey teams.
Rawlinson said she gained experience and appreciation for how the correct combination of capital and strategic operational expertise can improve the success of a sports franchise.
Applying those same practices to a WNBA franchise will be a new challenge, but Rawlinson embraces what she described as a “crucible moment” for the Sky and the league.
“I believe in the future of the team,” Rawlinson said. “This isn’t just a passion thing. This is a true financial asset for my family. You just don’t randomly invest in asset classes that you don’t think are going to give you returns, right? I believe in the future focus on the team. I think it’s a great bet.”
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A Lake Forest native, Rawlinson’s affinity for the Sky derives from a lifetime of Chicago basketball. She grew up during the golden days of the Bulls — trying to trick-or-treat at Michael Jordan’s house as a kid, celebrating her 16th birthday in the rafter seats of a game, sneaking out to take the Metra downtown with friends to celebrate the 1997 championship.
But Rawlinson also sees her new role with the Sky as an opportunity to invest in the many intersectional communities who are often overlooked in sports development, including women, people of color and the LGBTQ community.
As a Black woman, Rawlinson said she’s spent most of her professional career feeling othered. In the Sky, she saw a chance to commit to a different type of environment — a franchise created “for women by women, especially women of color.”
“You have to really navigate these spaces that weren’t built for you,” Rawlinson said. “I want to be able to pay it forward and make things better and easier for the next generation, the next woman, the next person of color, creating the future the way I believe it should be.
“If I can do that within institutions like sports, within women’s sports, within the W in particular and then in Chicago — you can’t get any better than that. “