U.S. specialty insurance firm to acquire SSRU

Chicago-headquartered Ryan Specialty has signed a definitive agreement to acquire Toronto-based Stewart Specialty Risk Underwriting Ltd. (SSRU).

Terms of the deal were not disclosed. The transaction is expected to close in the fourth quarter of 2025.

SSRU is a managing general underwriter (MGU) specializing in underwriting large-account, high-hazard property and casualty solutions. SSRU will become part of the Ryan Specialty Underwriting Managers division of Ryan Specialty, the latter firm says in a press release.

Founded in 2016 by Stephen Stewart, SSRU has established itself as a Canadian MGU with expertise in manufacturing, utilities, real estate, construction, and oil and gas.

“SSRU has built a robust distribution network that includes many global retail brokers and has capabilities across all 13 Canadian provinces and territories,” Ryan Specialty says in the release. “The firm’s breadth of expertise and consistent underwriting results have attracted the backing of multiple A-rated carriers.”

For its part, Ryan Specialty is a specialty products and solutions service provider for insurance brokers, agents and carriers. Founded in 2010, the firm provides distribution, underwriting, product development, administration and risk management services by acting as a wholesale broker and a managing underwriter with delegated authority from insurance carriers.

“We could not be more excited about the opportunity to welcome Stephen Stewart and the entire SSRU team to the Ryan Specialty family,” says Pat Ryan, founder and executive chairman of Ryan Specialty. “This very strategic transaction not only expands our capabilities in Canada but also represents a significant increase in the total addressable market that we serve.

“We are confident that the Ryan Specialty platform will greatly enhance the value that SSRU can deliver for its clients and trading partners.”

Ryan Specialty CEO Tim Turner adds SSRU has “a proven track record of disciplined underwriting and strong broker relationships. This acquisition allows Ryan Specialty to expand our Canadian market presence at scale…”

And SSRU’s “deep sector knowledge and national reach position us to deliver our broader product offering into Canada,” adds Miles Wuller, CEO of Ryan Specialty Underwriting Managers.

For SSRU president and CEO Stephen Stewart, joining Ryan Specialty Underwriting Managers allows the MGU to bring its expertise to a broader platform while maintaining the independence and discipline that defines its approach.

CAIB New Edition 1.0 – a New Standard for Broker Education Image

Insights Paid Content

CAIB New Edition 1.0 – a New Standard for Broker Education

Preparing brokers to navigate an increasingly complex insurance landscape.

By 

Sponsor Image

The release says SSRU generated approximately $18 million of operating revenue for the 12 months ending Sept. 30, 2025. This figure has not been audited and using current exchange rates, $18 million of operating revenue equates to US$13 million in operating revenue.

Jason Contant

Jason has been an award-winning journalist with Canadian Underwriter for more than a decade, including the past three years as associate editor and, before that, as digital editor for seven years.