Oliver Cunningham’s Career Story
Director, Valuation & Advisory Services – Colliers International
This series features the professional journeys of a wide range of individuals across Canada’s real estate development industry. Often, these stories highlight how rewarding careers in real estate development are the result of following your interests, fostering personal and professional networks, and keeping an open mind about what a career in real estate development might be.
Meet Oliver Cunningham – Director, Valuation & Advisory Services – Colliers International.
How did you get started in your career?
I started in real estate shortly after completing my Commerce degree at the University of Victoria. I moved back to Calgary and, on a friend’s recommendation, applied for a research position with Colliers and joined the downtown brokerage team. That role gave me a strong foundation in market data and trends and exposed me to the entrepreneurial culture at Colliers, which really clicked for me. After about a year and a half, I moved into the Valuation & Advisory team, where I’ve now been working for roughly 12 years, continually challenged and motivated by the mix of independence, responsibility, and client-focused problem solving the role offers.
Tell us a bit about your first job.
My first job was in the commercial kitchen at Sunterra Market when I was 14. It taught me how to handle several tasks at once, show up on time and be prepared for hard work, and develop strong interpersonal skills as I interacted with customers and co-workers every day. That experience set me on a path of enjoying fast-paced, team-oriented environments, which still carries through to how I work today.
Have you considered a career switch within or outside of the broader real estate industry?
When I was working full time and completing my AACI designation simultaneously, there were definitely moments when I questioned whether I could keep going. Balancing client work, coursework, work product submissions, and exams while trying to grow professionally was mentally exhausting, and I came close to throwing in the towel more than once. What kept me going was a commitment to finishing what I started and reminding myself how much time and effort I had already invested. Looking back, I’m very grateful I stuck with it, as it has led to opportunities and a career path I couldn’t have imagined ten years ago, and I’d encourage anyone in a similar situation to pause, recognize the progress they’ve already made, and keep climbing.
Who was your biggest influence or mentor in your career?
My biggest mentor and advocate has been my business partner, Adam Grisack. He was the one who really illuminated the AACI path for me and encouraged me to pursue and complete the designation. Since we began working together, we’ve built our own team and become very close friends, and it’s hard to imagine what my career would look like without his mentorship and the strong working relationship we’ve developed.
What is one project or achievement you are most proud of?
The achievement I’m most proud of is the team my business partner and I have built. At the beginning of COVID, it was just the two of us, and we made the decision to formally start our own team. Over the last five and a half years, we’ve grown to four people and nearly quadrupled our team revenue. More importantly, we’ve built a group that works well together, supports each other, and consistently delivers for our clients, which is something I take a lot of pride in.
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