But when a terrible injury cut that dream short, Thompson found herself working at Citadel Assurance straight after high school.
“Like most of my peers or colleagues, we all do the same thing – just sell into insurance,” she says.
That injury, however, would take Thompson to the top of insurance – from broker to president of the Insurance Brokers Association of Ontario and beyond.
Climbing the ladder
Thompson began to get serious about the business while vacationing in the Bahamas, where she met a broker from Gellatly Insurance, who encouraged her to obtain her broker license. For a few years, Thompson moved from Gellatly to HK&B (now HKMB HUB International) to RKS Insurance (which was later purchased by Sinclair-Cockburn Financial Group).
Over her 30-year tenure, Thompson rose through the ranks to become a partner at Sinclair-Cockburn. But in 2010, the company was purchased by Hub International.
“That purchase led to me having to sell my partnership, and I was out of a job,” Thompson says. “During this time, I was volunteering with IBAO, and it was through my connections at IBAO that I met Peter Blodgett and Judy Bell.”
Blodgett and Bell had opened a new brokerage just outside of Toronto called Beyond Insurance in 2008 – and they wanted Thompson to join their team.
“[Blodgett] said, ‘I don’t want you to make any sudden moves. I want you to think about an opportunity that I have for you with Beyond Insurance,’” Thompson remembers.
Thompson, however, had just been with a major player, and Beyond Insurance was a small brokerage in the Durham region, just outside the city.
While Thompson, who lives in Durham, says the idea of working in her home community was appealing, she still had her reservations.
“I’ve got to say, at first I wondered if I would be satisfied there,” she admits. “But what it’s allowed me to do is … leverage my experience to help them get into another space that they weren’t tapping into, which is the commercial lines space.”
Thompson came to the IBAO in 2005 as the territory director for the GTA and inspired her many peers and colleagues.
“She is passionate about the industry, and she passes that passion on to anyone she meets,” says Nadia Sartor, the head of broker relations for the IBAO.
Thompson says her work with the IBAO, in turn, made her even more excited about insurance.
“I think volunteering with our brokers’ association was a pinnacle for me,” she says. “The people I met and the experiences I gained really led me to believe in our broker system.”
In 2013, the same year she became a managing partner at Beyond Insurance, Thompson reached another pinnacle of her career: becoming president of the nearly century-old IBAO – a position only three women before her have held.
“When I first started, there was still very much a glass ceiling,” Thompson says. “For the longest time, the IBAO board – and not just the IBAO board, but many other boards in our industry – were made up of men.”
There were only three women on the IBAO board when Thompson started in 2005. Now, there are seven – including two on the executive team.
“The landscape is changing, albeit a little slowly, but it is changing,” Thompson says. “It’s ironic because our industry is made up primarily of women, but not always at the executive level. That tide is starting to change, and women are being seen more as leaders.”
Sartor says Thompson’s passion has spread through the industry like wildfire.
“It was a positive time,” Sartor says. “Debbie was not the first woman, but she was definitely the first black woman, and that speaks volume for the association. She enjoys great credibility within the industry itself. It was a positive thing for the association.”
Looking to the future
Thompson again has the opportunity to lead as managing partner for Beyond, which is made up of seven female brokers. She also uses her tech-savvy to move the brokerage forward.
“Before we’d say, ‘In 20 years from now…’ but now it’s in five years,” Thompson says. “So we have to make sure we’re providing a value proposition in that space and giving a great customer experience even though there’s not much human interaction.”
The strength of the broker distribution channel is an issue that Thompson is currently addressing in her work with Beyond, and one that she highlighted during her tenure as IBAO president.
“Being able to stand before the membership in 2013 as president and deliver a message that I strongly believe in – our distribution channel – was probably the highlight of my career, and a personal achievement,” Thompson says. “I’ve always been passionate about it, and being able to do that – it felt great.”
Thompson is also passionate about her three children, whom she raised as a single mother.
“Raising my three children has been my greatest achievement – seeing them become young adults and having a vision and very strong core values, and doing well,” she says.
Now that her kids are grown, Thompson is excited to inspire other young people via a new board she’s sitting on that will help develop youth entrepreneurship.
“[Today’s youth] live in a country where they can do whatever they want, dream as big as they can,” she says. “If you can inspire one person to dream, then you have done your job.”
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