Jill E. McCutcheon

Jill McCutcheon is a partner within the Regulatory Services Group and co-leads the Insurance and Reinsurance practice.  She specializes in insurance - corporate, regulatory and transactional matters. She provides advice to the property and casualty, life and reinsurance sectors of the insurance industry. She advises on all aspects of the law, whether federal or provincial, and acts as counsel to insurers, reinsurers, banks, credit unions, intermediaries, cover holders and MGAs, third-party administrators, retailers, employers and associations. 

Jill’s work includes acquisitions and dispositions of insurers and books of business; formation of new insurers; entry of foreign insurers; licensing of insurers and intermediaries; advising on and drafting pension buy-in and buy-out arrangements and related reinsurance solutions; drafting outsourcing, distribution and other specialized agreements germane to the insurance sector; advising on the requirements of the Insurance Companies Act and OSFI’s related guidelines; responding to regulatory inquiries and navigating regulatory investigations; and advising on compliance requirements and regulatory matters.

Jill is noted for her strong, longstanding relationships with the numerous Canadian insurance regulators and for her ability to anticipate, respond to, and resolve, issues with them on behalf of her clients. She has been widely recognized as a market-leading lawyer by Chambers Canada, where she is ranked Band 1, as well as by Lexpert, Who’s Who Legal: Insurance & Reinsurance and other leading directories. Jill has twice received the Lexology and International Law Office Client Choice Award for insurance and reinsurance in Canada/Ontario.

"Jill McCutcheon is an excellent adviser with a deep understanding of the regulatory insurance landscape. She provides valuable guidance on complex questions and novel ideas."
— Chambers Canada 2024