McDougall Insurance Brokers Limited has entered into a strategic partnership with Tailored Insurance Services Inc., a boutique brokerage based in Richmond Hill, Ontario, that focuses on commercial program business.
Tailored is a portfolio-driven firm with specialist programs for machine shops, photography and graphic design, as well as broader commercial and personal lines.
Through the deal, McDougall aims to broaden its program access across its growing national footprint, drawing on Tailored’s niche expertise while using McDougall’s scale and market access to extend Tailored’s reach and service capabilities.
The move comes during an active period of consolidation in Ontario’s brokerage market, where large acquirers have been targeting the province to build scale and deepen distribution.
McDougall said the partnership continues its inorganic expansion in the Greater Toronto Area (GTA).
The broker acquired Markham-based Cornell Insurance Brokers Ltd. in a merger that closed on December 2, 2024, bringing more than 50 staff and a full-service personal and commercial offering into the group while retaining the Cornell brand. Cornell has since combined with Etobicoke-based Active Insurance & Financial Group to strengthen McDougall’s presence in the Toronto market.
Under the new arrangement, Cornell and Tailored are expected to work closely together to make use of Tailored’s program capabilities and McDougall’s broader infrastructure.
“Tailored was a rare opportunity for us to partner with a business that both shares our entrepreneurial culture and brings new expertise and options for us to provide to our clients,” said Lorne McDougall, vice president at McDougall Insurance. “We are confident that our collaboration will produce meaningful gains for the clients of both organizations and we appreciate this opportunity to further build our story in the GTA.”
Tailored’s president, Gary Spry, will remain with the business following the deal.
“This process was motivated by customer service,” said Spry. “Tailored takes its obligations to clients very seriously – and partnering with McDougall gives Tailored’s clients access to a market-leader in our industry while providing Tailored access to a wealth of opportunity nationally. We look forward to collaborating with McDougall to take our respective businesses to the next level.”
McDougall said it is committed to supporting Tailored in maintaining the standards of professionalism and customer service that Tailored’s clients expect.
Founded in 1946, McDougall is one of Ontario’s largest P&C brokerages, representing more than 50 insurance companies and operating through over 40 branches with more than 450 employees. Definity Financial Corporation first took a stake in the firm in 2017 and later increased its ownership to a majority interest, backing an acquisition program that saw McDougall complete multiple broker deals and more than double its annual premium base to about $500 million.
Definity later announced a $232 million transaction combining McDougall with fellow Ontario broker McFarlan Rowlands, creating a platform with more than $700 million in annual premiums, about 670 employees and 57 locations, with a stated ambition to expand nationally.
McDougall executives have described their M&A approach as a “Goldilocks” strategy focused on culturally aligned, mid-sized firms rather than purely pursuing geography or product mix. The Tailored partnership fits that pattern, adding a specialist commercial-program capability while reinforcing McDougall’s position in the GTA, Canada’s largest and most competitive commercial insurance market, the company said.
