Jennifer Reynolds never feared a career jump — and it led to the role of her dreams.
The senior manager of equity, diversity and inclusion with Maple Leaf Sports and Entertainment shares her journey.
By Hailey Eisen
Jennifer Reynolds’ LinkedIn banner image shows her marching in the 2019 Toronto Pride Parade. She’s wearing a T-shirt that says Hockey for Everyone, and there’s a huge rainbow Raptors banner behind her. The moment captured in the photo represents the culmination of years of hard work, risks taken, unexpected opportunities, and a commitment to making an impact while following her passions.
“I was marching alongside 50 of my colleagues down Yonge Street right after the Raptors championship win,” Jennifer recalls. “As a Queer woman and an athlete, to see the delight in people’s eyes, and to hear the chanting and spirit, was an extremely meaningful and memorable experience.”
Now the senior manager of equity, diversity and inclusion (EDI) with Maple Leaf Sports and Entertainment (MLSE), Jennifer didn’t set out with the intention of working in the sports industry, or EDI for that matter. She’s a chartered professional accountant by trade and describes her career journey as more of a jungle gym than a ladder. “I often advise people that the education you choose, and the first job you get, doesn’t have to dictate your career direction or where you’ll end up — rather, look at each opportunity as a stepping-stone.”
Jennifer’s first stepping-stone was a move from Calgary (where she grew up) to Kingston to complete her undergraduate degree in Commerce at Smith School of Business, Queen’s University. She focused most of her studies on accounting.
“My experience at Queen’s was really well-rounded. I participated in extracurricular clubs and conferences with the Commerce Society, I played intramural soccer and basketball, and excelled on the varsity triathlon team. I was also able to focus on my studies alongside other really talented students. I gained international experience and got to travel around Europe on an exchange semester to London, which was truly an enriching opportunity,” she says.
After graduating, Jennifer moved to Toronto, joined KPMG and worked towards her professional accounting designation on the side. “Though I loved accounting, I came to realize that being an auditor didn’t fully align with my core strengths and so I joined Deloitte’s mergers & acquisitions group in 2015 where I had the opportunity to provide value to clients in a more dynamic environment.”
“It can seem scary to make these kinds of career jumps early on, but it’s important to keep your own best-interests and passions in mind.”
It was then that she says she really began to think about the idea of stepping-stones. “It can seem scary to make these kinds of career jumps early on, but it’s important to keep your own best-interests and passions in mind…Your studies, plus your lived experiences in the world, can lead to so many different things. What’s most important is that you believe in yourself, advocate for your own success and take steps to plan your own journey.”
During her three years with Deloitte, Jennifer says she experienced huge learning and growth. “I became a manager, found myself within the business world and had an entrepreneurial opportunity to help develop and grow Deloitte’s mergers and acquisitions practice, defining the roles and responsibilities as I went along.”
When the opportunity at MLSE presented itself, it seemed like a dream to the self-described sports fan. While she was happy in her current role, what MLSE was looking for in a manager of corporate strategy and planning aligned quite well with her skillset and passions. “It was hard to leave Deloitte, but I was excited to apply everything I’d learned in the first years of my career to an end product I was really passionate about.”
Jennifer had the opportunity to build out the role — supporting the organization’s CFO and senior executives when it came to strategic business planning across a variety of projects. “It was quite amazing to be working on projects that I’d seen and experienced as a sports fan and getting to understand them from the business side.”
Fast forward to the summer of 2020, a time when many organizations were facing an internal reckoning of sorts, following the murder of George Floyd and the rise of the contemporary Black Lives Matter movement. MLSE realized that they could be doing more with their strong community presence at both the local and national level. “We had so much influence in our city and such a global fanbase that we recognized we had a huge platform to take a more active stance when it came to social justice.”
That fall, MLSE brought in an SVP equity, diversity and inclusion. Jennifer recognized an opportunity for herself to pursue something she was really passionate about. “I had always been involved with different community projects, with equity work on a volunteer basis,” she says.
“Being able to make that impact at a grassroots level first to now working in the professional sports space, I’ve come to realize just how much work there is to be done and just how powerful the impact can be.”
In 2016, Jennifer became the Canadian board co-chair for the You Can Play Project, an initiative with a mission to ensure the safety and inclusion for all who participate in sports — including LGBTQ+ athletes, coaches and fans. “Being able to make that impact at a grassroots level first to now working in the professional sports space, I’ve come to realize just how much work there is to be done and just how powerful the impact can be.”
She was also a driving force behind the creation of the Queen’s Queer Alumni Chapter. “There was a gap when I was a student in supporting and providing structure for queer students, which is what propelled me forward to co-found this chapter,” she says. “As alumni, we play an important role in supporting queer students and making the Queen’s community a more inclusive place for all.”
So when Jennifer learned that MLSE was bringing Teri Dennis-Davies — an HR professional with experience leading the design, development and implementation of EDI strategy and initiatives — she knew there would be a need for someone to support her efforts. “I wanted to be that person,” Jennifer says.
She raised her hand, and in November 2020 she stepped into her current role — senior manager of equity, diversity and inclusion — helping to build a department and set the inclusion and engagement framework and strategy for the entire organization.
“I’ve been in this role now for just over 18 months, but it certainly feels a lot longer with everything we’ve accomplished,” Jennifer says. “We have a huge focus now on addressing racism and social justice with an emphasis on three pillars: eliminate barriers, accelerate development, and change lives.”
“Remember that no change or action is too small, and everything contributes in some way to larger shifts. The key is to begin, one step at a time.”
Part of a team of six across an organization of 4,000 employees, Jennifer says she knows that true impact comes from empowering every employee within MLSE to be an agent of change. In February 2021, MLSE made a public declaration to address systemic racism and promote social justice, both within their workplace and in their community. “For a privately held organization of our size, this was a big step for us — and internally we’ve had great success in upholding this commitment. I’m really proud.”
A recent opportunity has come up to take on an expanded portfolio focusing on inclusion for the Toronto Maple Leafs franchise. “It’s been eye opening working alongside the Leafs’ front office, promoting inclusion both within the business side and community side — and seeing a tangible impact of the work we’re doing,” she says. “We acknowledge that professional hockey is typically a white male-dominated sport, and there’s a huge role the Leafs can play to break down those barriers.” One of the ultimate goals is to mirror the diversity of Toronto in the Leafs brand, employees and fanbase.
Looking at all she’s accomplished in a short time, Jennifer is often in awe of how perfectly her passions and career are aligned. “I’m so fortunate to be in this position, to have the influence that I have and the platform that I have.”
As a mentor to young professionals, she says many look to her for guidance when it comes to following your passion and making real change. “You know, there’s always the potential for change in any field and in any organization,” she says. “Sometimes you need to step back to reflect upon how much change has actually taken place, and you’ll often see that there’s more happening than you realize. Remember that no change or action is too small, and everything contributes in some way to larger shifts. The key is to begin, one step at a time.”