Chris Overholt has had a long and prosperous career in the sports industry, joining the Toronto Raptors in 1996 before ultimately playing a part in the growth and success of the Toronto Maple Leafs, Florida Panthers, Miami Dolphins, and the Canadian Olympic Committee. Now he’s made the move into esports as CEO of OverActive Media 
, the holding company behind Splyce and the Overwatch League’s Toronto Defiant.
Despite his robust career in the industry and interest in sports from a young age, however, he never had big dreams of charting such a path through life. “I certainly didn’t grow up thinking I’d be working in the sports and entertainment business,” he said. “I was liberal-arts educated at the university level, and actually studied history.”
Overholt spent about a year traveling the world after graduation before taking a job in the insurance industry, and he credits the position with helping to hone his communication skills in a business setting. Following a brief stop in computer sales, a past university contact reached out about joining the Toronto Raptors in a sales capacity. The team had just completed its first season in the league, and for Overholt, it was a chance to do something totally new.
He joined and led the sponsorship sales department for his first two years with the team, and after the Toronto Maple Leafs owners bought the team and combined them under the Maple Leafs Sports & Entertainment banner, Overholt shifted his focus to driving ticket sales for both teams. The Toronto native quickly found himself in a leadership role for the city’s NBA and NHL teams.
“I certainly didn’t grow up thinking I’d be working in the sports and entertainment business.”
“It was an absolute dream come true,” he said. “I didn’t grow up thinking that it would even be possible, of course—but all at once within a couple of years, I not only find myself in the sports business, but working for the brand new NBA franchise in Toronto and the franchise that I and most of us here in Toronto grew up watching every Saturday night. It was fantastic. I had such a good experience at Maple Leaf Sports.”
Overholt stayed with Maple Leaf Sports & Entertainment until 2003, when he started getting the itch to pursue another opportunity. Although he loved working there, he said that the mass of young, executive talent was so strong that he didn’t see a very good chance to continue progressing in his career. Once more, he sought a new kind of challenge.
Credit: lolesports/Riot Games
“I didn’t see that I was going to have the opportunity to grow into a senior role at Maple Leaf Sports,” he said, “and I wanted that for myself and wanted the chance to grow.”
For that, Overholt shifted gears and moved to South Florida to join the NHL’s Florida Panthers, where he served as executive vice president of business operations and chief marketing officer. It was a major change for both Overholt’s career and his family, but he says that his clan appreciated the change of scenery. “The weather was welcomed by all of us,” he said. “There’s something about blue skies and palm trees that’s good for the soul.”
“There’s something about blue skies and palm trees that’s good for the soul.”
In 2005, he moved over to the Miami Dolphins as vice president of corporate partnerships and broadcasting, and stayed with the NFL team until 2010. Once more seeking a new opportunity, he considered options in Europe before catching an offer back in Toronto from an unexpected party: the Canadian Olympic Committee (COC). “You’re presented with things that come along in life, and it seemed unreal to me that I was being presented with the opportunity to work for the Olympic Committee,” he said. “I certainly took the meeting.”
As the COC’s chief marketing officer and chief operating officer, and soon after its CEO, Overholt helped rebuild momentum around the movement following 2010’s Vancouver Winter Olympics. He led a restructuring of the organization, drove corporate sponsorships, and spearhead initiatives that provided funding for national sports federations, helped transition retired competitors into new careers, and supported LGBTQ athletes and allies.
Credit: OverActive Media
“Of all the things I’ve been lucky to have the chance to participate in, I think my time in the Olympic movement is what I’m proudest of,” he said. “It is a special organization.”
If there’s a common thread that runs through Overholt’s myriad career moves, it’s a yearning to continue pushing forward and not become complacent in any one role or business. It’s what has driven him from insurance to computer sales and prominent roles in three major traditional sports leagues—and now what has pulled him into the previously-unfamiliar world of esports.
“This seemed like a great opportunity for me to redefine myself—an opportunity to learn a new industry…”
“I’ve always tried to evaluate new opportunities as an opportunity for progression for me to learn more,” he said, “and to have a broader set of experiences and to work with different leaders—and find new ways to be successful in new industries.”
His introduction to the group that would eventually become OverActive Media came via Sheldon Pollack—now OAM’s chairman—a contact that Overholt first made in that computer sales role more than 20 years prior. Overholt had already spoken with Activision Blizzard about Overwatch League in 2016 and evaluated the possibility of entering esports then, but didn’t make a move. When asked for advice last year about potentially acquiring the Toronto franchise, Overholt felt that the timing was right to make that next major career leap.
Related Article: OverActive Media CEO on Acquiring Splyce and Seeking Future Franchises
“It’s funny how things work out sometimes in life, and it just goes to show you that every relationship, everybody you meet along the way in your life and your career, they’re all an opportunity to build relationships and build personal connections with people,” he said. “You never know where life takes you and the opportunities that might arrive, and in this case, I got what I think in the end is going to be a life-altering call from Sheldon Pollack to enter into an industry that I think is exploding right in front of us.”
For Overholt, joining OverActive Media not only thrust him into an entirely new industry, but it is also his first experience working in a startup environment. However, he’s always seen himself as a builder in past roles—so while there are adjustments to make, he’s felt well-poised to adapt to the new challenges thrown his way.
“More than that, it’s been a great opportunity to learn a bunch of new skills.”
“I’m 54 years old, and when you get to be this age—sometimes, if you’re not paying attention, you find yourself in a place where you’re no longer relevant in what you might be doing,” he said. “It doesn’t have anything to do with the age, but if you’re just going along in your career and you’re not mindful of growing, and you’re not thinking about how you’re going to progress and learn new things, then sometimes before you realize that you’re stuck in a place that you can’t escape from. It can all be over before you’re ready.”
“This seemed like a great opportunity for me to redefine myself—an opportunity to learn a new industry, work with new people, build something from scratch, and to be relevant in that conversation,” he continued. “All of that seemed to be a great progression for me, and it was something that I still felt like I was young enough and had the energy for. It’s not the scale that I’ve been accustomed to in recent years, but it’s going to be. More than that, it’s been a great opportunity to learn a bunch of new skills.”
Credit: OverActive Media
While OverActive Media has already made a big splash in the esports scene, the company is currently much smaller than the kinds of organizations that Overholt has worked in over the past two decades. And he’s fine with that. He sees this as an opportunity that will grow and expand over time, and today’s modest deals could ultimately lead to much larger things in the future. As he told The Esports Observer last year, Overholt wants to follow the Maple Leaf Sports & Entertainment model and establish the same kind of iconic company in esports. That’ll only happen one step at a time.
“I’m really excited to be in the circumstance that allows me to be part of that story.”
“I’m out talking to marketing partners frankly about deals that aren’t about many millions [of dollars] today,” he said. They’re about literally tens and hundreds of thousands to get them started, and I’m entirely OK with it. Because I know all of what comes with it, right?”
“I imagine what it’s going to look like five years from now and how proud we’re going to be in what we’ve done,” he continued, “and the hand that we’re going to have had not only writing the narrative for esports in the country, but certainly shaping how the world thinks about OverActive Media in an industry that I think is going to be one of the biggest things that we’ve ever seen in the next five to 10 years. I’m really excited to be in the circumstance that allows me to be part of that story.”
