2025 Underwriters of the Year | Brittany Siwak, Commercial Auto Specialist, Aviva Canada

With over a decade of experience in the industry, Brittany Siwak brings deep technical expertise and a strong sense of purpose to her role as a Commercial Auto Specialist at Aviva Canada. Siwak began her career as a commercial auto claims adjuster, which gave her a solid foundation before transitioning into an underwriting assistant role. Over the years, she rose through the ranks to her current role, specializing in medium-enterprise insurance and mid-market auto accounts.

Siwak holds a bachelor’s in Health Studies from McMaster University. A proud mom to Beau, 6, and Mila, 3, Siwak loves golfing with her family, reading, shopping, and staying active with her children.

Siwak says being recognized by Lawrie Insurance Group, a member of the Canadian Broker Network — Canada’s largest network of independent brokers — is “truly meaningful. It reinforces the value of the work I do and motivates me to continue striving for excellence.”

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

“Trust, transparency, and open communication. When both parties understand each other’s goals, it creates a collaborative environment where we can find the best solutions for clients.”

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

“I was first introduced to the insurance world through my mom, who is a commercial lines broker. I was drawn to underwriting specifically by the challenge and complexity of assessing risk. I enjoy the technical side of the role most — no two files are ever the same and that keeps the work engaging. The constant evolution of the industry means there’s always something new to learn — something I truly value.”

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

“Navigating a tough market is the biggest challenge. While pricing matters, what really differentiates us as a company is our service. In a competitive landscape, responsiveness and consistency, paired with strong broker relationships, make all the difference.”

Q: What’s one opportunity underwriters should focus more on?
“Strengthening broker relationships through proactive communication and education. We should also be leveraging telematics data more effectively to understand driver behaviour and fleet performance. That way, we can add value beyond pricing by identifying areas for improvement.”

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

“The industry is constantly evolving, offering new challenges and opportunities. It’s a great space for analytical thinkers, problem solvers, and relationship builders.”

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

“AI and machine learning are transforming our world. These tools help us process data more efficiently and identify patterns more accurately, which enhance the service we provide. But human judgment, relationship-building, and contextual understanding will always be essential.”

Q: What skills are needed for underwriting leadership?

“A blend of technical expertise, strategic thinking, and strong interpersonal skills. Communication and adaptability are key. Building trust with brokers doesn’t just grow business; it opens doors for career growth, too.”

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?

“Auto underwriters have an opportunity to work with brokers to communicate emerging risks like auto theft. We can recommend theft prevention tools like TAG or KYCS and share data trends. That helps brokers guide clients more effectively, which leads to better risk management and stronger outcomes for everyone.”

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