Flexibility is key to Sutton Special Risk’s success

One of the highlights of her career as an insurance underwriter at Sutton Special Risk, Inc., according to Renee Sands, is a week she spent in London on an exchange with employees of Sutton’s U.K. partners.

“It was great to have the opportunity to watch them go about their job,” she says. “It was also nice to get to know them on a face-to-face level. Just having access to high-level colleagues and business partners and having them host us was very unique, and I’d be surprised if other companies offered the same thing to their younger employees.

“London was an incredible experience, and I feel we came back to Toronto with enhanced perspectives and got to strengthen our business relationships in person.”

For president and CEO Greg Sutton, that opportunity echoed his own early experience at the company his father founded in 1978 to create special insurance policies for clients with unusual needs.

He was sent to London for two years to work with Lloyd’s of London, a global industry leader, and remembers how he made “some really long-lasting connections that have been vital to our business to this day.”

“I’m glad Renee mentioned that trip,” he says. “We try to allow for those sorts of experiences. Not only does it provide a change of pace and scenery, but to go over there and see how we’re connected to our business partners and learn first-hand positive opinions on our capabilities, it makes our people here feel more connected to what we do and gives them an idea of our reputation and the impact of our strong relationships.

“We like to say we’re a small company with large-company capabilities,” says Sutton. “We are extremely agile, allowing us to offer a more bespoke solution — to work with the client to offer the product that meets their risk exposure. It puts us in a position to compete with larger carriers.”

Sands says working in a smaller office like Sutton’s makes communication much easier, which is crucial when tailoring client policies. “You can be on an underwriting team and ask questions to the finance team by walking over to their department. You feel comfortable doing something like that. You don’t have to set up formal meetings.”

With so much shared knowledge in the office, employee retention is key. Sutton talks about matching employees’ RRSP contributions, and health plans that cover everything from drugs and dental to wellness and critical illness, but adds that team volunteering events are critical to “bring people together for a common goal, to know how important it is to give back.”

At Sutton, employees have the opportunity to suggest organizations or causes they are passionate about. This not only empowers employees to engage with issues that matter to them but also fosters a deeper sense of connection between the company and the community.

For Sands, that meant organizing a blood drive. “I was really encouraged to do this as a team thing, to take the initiative and make it happen, to work with causes where we have a connection.”

This article appeared in the magazine announcing this year's Canada's Top Small & Medium Employers winners, published April 8, 2025 in The Globe and Mail. This article was prepared with the financial support of the employer, which reviewed but did not write its contents.