Kimberley Medeiros’s career trajectory has been anything but linear. With a dream of becoming a teacher, she never imagined that earning a master’s degree in education would take her from the classroom to the boardroom.
Starting as a substitute teacher with the Windsor Essex Catholic District School Board, Medeiros secured a long-term placement teaching high school English before specializing in elementary special education.
Hoping to “open new doors” in her career, she enrolled in the course-based Master of Education program at the University of Windsor, focusing on curriculum development.
“I felt like it could be manageable while working full-time and help open doors for me within the teaching profession,” Medeiros reflected.
While completing her studies, she was inspired by her professors to consider roles beyond the traditional classroom setting.
“A lot of teachers and educators don’t necessarily know how many career opportunities await them outside of the classroom,” she noted.
Graduating just three weeks before the birth of her first child, Medeiros relocated to Toronto, where she worked for the Toronto Catholic District School Board, focusing on students with autism. It was here that she discovered the Build Our Kids’ Success (BOKS) program, which aimed to engage students through physical activity.
“One student I worked with was extremely active and was better able to learn and socialize when he was active in the mornings,” she explained.
“I began searching for resources and soon discovered BOKS — a partnership between Reebok, the Public Health Agency of Canada, and the CFL that provided free physical activity resources to schools to get kids active. It was perfect for my student as it was focused on movement, not sports.”
Recognizing the program’s impact, Medeiros integrated it into her classroom and subsequently reached out to Reebok to explore employment opportunities.
“I was really excited at the idea of joining the corporate world, especially in a role focused on outreach to schools across the country.”
Transitioning from teaching to the corporate sector was a significant leap, but Medeiros was able to use her curriculum development skills and knowledge to help modify and improve the existing BOKS curriculum to meet Canadian standards.
“It was really rewarding to be able to leverage my knowledge and skillset in such a tangible way.”
What began as a one-year contract turned into eight years, three promotions, and countless learning experiences.
In 2022, after Reebok was sold and BOKS disbanded in Canada, Medeiros secured a contract with Tennis Canada, helping to launch its Gender Equity in Sport Strategy.
Today, as director of community, government relations, and corporate citizenship at Woodbine Entertainment, Medeiros blends her educational background with a passion for community engagement and corporate responsibility.
Reflecting on her time at the University of Windsor, Medeiros emphasizes the lasting impression of her experience.
“The focus on innovation, collaboration, and creativity in the Master of Education program teaches transferrable soft skills that are valuable anywhere,” she said.
“To be honest, the boardroom is not that different from the classroom sometimes! I still focus on creating creative solutions to challenges, and I’m not afraid to admit when something isn’t working.”
Medeiros’ commitment to her own growth and education is part of what has allowed her to embrace adventurous career choices and set her apart in the job market.
Her latest project involves the revitalization of Woodbine’s Community Garden, where a local non-profit educates aspiring farmers traditionally excluded from agriculture due to race, gender, or socio-economic status. The farmers cultivate the land and donate hundreds of pounds of fresh vegetables to local racetrack employees, helping combat food insecurity.
“Myself and my colleagues now use our lunch hours and volunteer in the garden. It is extremely rewarding to see work like this come to fruition,” Medeiros said.
Monte McNaughton, Woodbine Entertainment’s executive vice-president of industry relations and people experience, describes Medeiros as a leader.
“Her commitment to our community is demonstrated every day,” he said. “She helps lead the Woodbine Cares Community Garden initiative, which is Canada's largest corporate community garden. This project — and a winter food program for our backstretch workers — is just a few examples of Kimberley giving back. She leads by example, and in turn, inspires others at Woodbine to do the same.”