In order to make the Ottawa BlackJacks a viable sports club, president Jason Winters knew he had to beef things up. In less than a year, he’s grown the front-office team exponentially. In September 2025, the Ottawa BlackJacks, members of the Canadian Elite Basketball League, were acquired by Diamond Sports Canada Inc. Winters became the […]
Get Instant Access to This Article
Become an Ottawa Business Journal Insider and get immediate access to all of our Insider-only content and much more.
In order to make the Ottawa BlackJacks a viable sports club, president Jason Winters knew he had to beef things up. In less than a year, he’s grown the front-office team exponentially.
In September 2025, the Ottawa BlackJacks, members of the Canadian Elite Basketball League, were acquired by Diamond Sports Canada Inc. Winters became the team’s president last October. He also bought into the team as a partner.
“I have a vested interest in the city and the growth of this team,” he said. “It was a big decision to get into this, financially and emotionally. This team is a direct reflection of (me and my family). If we do bad, it’s on us.”
Last fall, Winters said he had three “boots-on-the-ground” employees. “Everything was run out of the league’s head office. So all of the things that people (saw in Ottawa) were run out of the league,” he explained, saying the three employees basically did what the league asked of them.
With a view to growth and establishing the team in Ottawa, Winters said he assessed where he needed to hire and got to work finding the right people.
“I needed (someone in) sales. There’s obviously the ticketing and corporate (partnerships) side of that. We needed brand and creative and then the holistic side of community (engagement). In January or February, you start looking at the true basketball team. Then, finally, the last piece of it was game day (operations). By that, I mean someone working with (the Ottawa Sports and Entertainment Group). This someone needed to know how to liaise between OSEG and what we needed on the court,” Winters explained.
By the time the 2026 season kicked off in mid-May, Winters said he’d gone from three to seven full-time staff. That number ballooned to more than 35 over the summer, with the addition of players on the court, contract basketball operations staff, physical therapists, equipment managers and interns. Now in the off-season, the front office counts eight employees.
“From those seven, we built a fully functioning professional basketball organization that, during the season, grew to more than 5x that size — while delivering a professional game-day experience and welcoming 25,000+ fans to TD Place this year,” Winters wrote in a recent LinkedIn post.
“This kind of growth doesn’t happen because one person has all the answers,” the post continued. “It happens because you find people who are great at what they do, believe in what you’re building, and are willing to roll up their sleeves and get the job done. Scaling isn’t simply about adding more employees. It’s about adding the right talent, the right leaders and the right culture at the right time.”
Speaking to OBJ last week, Winters said his staff was able to work effectively by acting as a team.
“You play for the logo on the front, not the number on the back, and it’s something that’s big amongst my staff,” Winters said.
Alex Forbes, creative brand and brand manager for the BlackJacks, said every front office employee has a dedicated role but can sub in for a colleague if needed.
“We’re still a fairly lean team. We all work closely together, understanding each other’s roles and how they all work to achieve different goals … It wasn’t (about) reliance on one person,” Forbes said.
That mindset has translated into tangible results, Winters told OBJ. In the 2025 season, before Diamond Sports Canada acquired the team, there was a 53 per cent season seat renewal rate. For the 2026 season, 83 per cent of season seat ticketholders renewed for the next season.
“That’s a direct reflection of everyone’s work,” Winters said. “We’re up on every business metric year-over-year.”
As team president, Winters said he’s brought some of his best practices from a career in business, including serving as general manager of Myers Kanata Nissan and owner and operator for multiple Booster Juice franchises in the National Capital Region.
“In the car business, you really learn how to manage multiple departments and people at a time. You learn time management and get rid of time-wasters. It allows your staff to grow. I make it a point every day to talk to every staff member and ask them if they have all the tools they need to do their jobs. If it’s a no, I go and find the tools,” he said.
“Knowing your staff, knowing their strengths and, a lot of people may not understand this, but knowing their bandwidths. Everyone’s got a bandwidth, no matter who they are and what they do ... It's really about understanding who they are outside of your four walls because you can’t do it alone.”
Outside of staffing, Winters said the BlackJacks front office is always keeping score - literally. With a scoreboard in the corporate offices, he said the team keeps an eye on its weekly, monthly and yearly progress against goals.
“I find a lot of businesses get stuck on year one. It’s really simple. If you have a target of x, every manager should sit with their staff and divide the task by 12. You’ve got 12 months to do it. Then, take the task and divide it by 21 or 22 workdays. The number just got smaller. Now, your employee is like, ‘Okay, it’s more manageable’ … One a day or 0.5 a day is much easier than 100,000,” he explained.
On the court, the BlackJacks lost in the eastern conference semi-finals to the Brampton Honey Badgers, winning 10 regular-season games and losing 14. About 2,500 fans watched every BlackJacks home game from the stands during the 2026 season.
In the off-season, Winters said the team will be looking to grow community outreach with its BlackJacks Everywhere tour, where players take over gym classes around eastern Ontario to show kids how to play basketball. On the corporate side, the team has just launched its Workplace Rewards program, where participating businesses get 20 tickets to every home game and brand visibility.
Winters said the team is in planning mode, having just wrapped up the business plan for the 2027 season. Forbes added that the front office is thinking about how to make the BlackJacks experience just as exciting in the 2027 season.
“We have a great season ticket renewal rate. People were very happy with what they saw, but how I take it from the marketing side is, ‘What are we going to do next?’ I think we did set the bar pretty high on a lot of stuff, with halftime entertainment, exciting players and a great overall experience. How do we elevate the brand? How do we elevate the experience? I think having a full off-season together as a team is really going to show what we’re capable of bringing forward into the next season,” he said.
