Stephen Stewart

Stephen Stewart is the founder of Stewart Specialty Risk Underwriting Ltd. and Chief Executive Officer of Ryan Specialty Canada Limited. An insurance industry veteran with more than 30 years of experience, he built his career from early roles in brokerage, business development, and underwriting to leading the Canadian operations of an international specialty insurer. His experience spans the domestic, U.S., Bermudan, and London markets on both the carrier and brokerage sides.

Mr. Stewart founded SSRU in 2016 and developed it into one of Canada’s leading specialty MGAs, recognized for disciplined underwriting and strategic capacity partnerships. Following its acquisition by Ryan Specialty, he was appointed CEO of Ryan Specialty Canada Limited, where he now leads the national platform and oversees all Managing General Underwriting operations across Canada. In this role, he is responsible for strategic growth, regulatory governance, carrier relationships, and the continued expansion of Ryan Specialty’s Canadian footprint. Mr. Stewart holds an unrestricted RIBO license, as well as CAIB and FCIP designations.