2025 Underwriters of the Year | Cara Barry, Commercial Auto Trading Underwriter, Economical Insurance

With more than 13 years at Economical Insurance, Cara Barry is a seasoned underwriter with a passion for relationship-building. While her early experience included time on the broker side, Barry has spent most of her career in underwriting, beginning in Facility Association on the commercial team and steadily progressing from there to her current role as a Commercial Auto Trading Underwriter.

She holds a business diploma from the Southern Alberta Institute of Technology. When she’s not working, Barry enjoys many hobbies, including ultramarathoning, raising chickens, keeping horses, and creating soaps and lotions. She also gardens, hikes, knits, and spends time with her three dogs.

Barry says being recognized by Acera Insurance, a member of the Canadian Broker Network — Canada’s largest network of independent brokers — came as a surprise, and she feels honoured. “I’m extremely grateful to get to work with a wonderful group of brokers.”

Q: What’s key to a great working relationship between underwriter and broker, and why is this more important than ever?

“Picking up the phone. These days, many people prefer email, but real conversations — whether over the phone or visiting brokers in person — are essential to building strong relationships.”

Q: Why did you become an underwriter, and what do you love most about your role?

“I’m not one for veering into different roles and always stuck to underwriting once I first became one. What I love most today is the people — my co-workers and the brokers —and the broader connections with many different people. And there’s always something new to learn.”

Q: What’s the biggest challenge for underwriters today, and how can they overcome it?

“There are many, but market conditions is a big one. It has become incredibly difficult to price new business competitively while maintaining profitability, especially given the impact of Cat events. Staying informed on what other markets are doing, sharing information, and working collaboratively are essential.”

Q: What’s one opportunity underwriters should focus more on?

“Specialty market segments and using technology like telematics to better tailor coverage in areas like transportation. It gives us the chance to align pricing with real exposures and offer more meaningful solutions to policyholders.”

Q: Given that talent shortages remain a challenge, what would you say to encourage more people to join the insurance industry?

“Historically, our industry offers real stability, along with huge potential for growth and career development. With so many evolving industries, coverage requirements, and exposures, insurance always offers the chance to keep learning and stay ahead of emerging risks.”

Q: How do you see AI and technology impacting underwriting?

“I was skeptical at first, thinking it might replace underwriters. But it has become a powerful tool that’s great for improving efficiency, helping us answer broker questions faster, and even supporting learning. Still, it’s not always 100 percent accurate and can’t replace human judgment or common sense when reviewing risk.”

Q: What skills are needed for underwriting leadership?

“A growth mindset, strategic thinking, and strong communication. The ability to collaborate and adapt is essential, not just within your team but also with broker partners and industry peers.”

Q: Canada continues to suffer pressures like natural catastrophes, auto theft, fraud, and tariff impacts. How can brokers and underwriters better collaborate to help Canadian consumers manage risk?

“It starts with sharing information and being transparent. We can work together to educate one another and even create programs that support risk mitigation. That, in turn, will help us empower policyholders.”

The Canadian Broker Network Underwriter of the Year awards is a flagship program that CBN has been running on behalf of its members for over a decade. The program is exclusive to CBN in partnership with Canadian Underwriter magazine. The categories allow for each of our member firms, at their option, to select one commercial lines underwriter winner and one personal lines underwriter winner from a primary market, as well as a commercial underwriter from an MGA. The criteria includes underwriting excellence and risk knowledge; prompt and effective responsiveness back to CBN members; writing business that satisfies clients’ needs while creating a win-win for the broker and the insurer; a positive, helpful attitude; and investing time to develop trusting relationships with brokers.

Full list of 2025 Underwriter of the Year Award Recipients