Jill E. McCutcheon
Automatically compiled listing. Details may contain errors.Partner at Gowling WLG
- Called to the bar
- 1989
- Languages
- English
Insurance LawInsurance LawAbout Jill E. McCutcheon
Insurers, reinsurers and the businesses around them turn to Jill McCutcheon for corporate, regulatory and transactional insurance work. A partner in Gowling WLG's Toronto office, McCutcheon co-leads the firm's Insurance and Reinsurance practice from within its Regulatory Services Group, and serves clients across property and casualty, life and reinsurance. Questions can fall under federal or provincial law, and the client list runs well beyond carriers to banks, credit unions, intermediaries, MGAs and third-party administrators.
On the regulatory side, McCutcheon advises on the Insurance Companies Act and OSFI's guidelines, handles inquiries from regulators, and guides clients through investigations. The work also means dealing directly with Canada's insurance regulators on clients' behalf, anticipating issues and working to resolve them.
Called to the Ontario bar in 1989, McCutcheon joined Gowling WLG in 2026 after more than nine years at Torys, where the role included co-leading its financial services regulatory practice. Chambers Canada ranks McCutcheon in Band 1 for insurance, and the partner spoke at the CLHIA's compliance and consumer complaints conference in both 2025 and 2026. Outside the office, McCutcheon sits as a director of the Ladies First Hockey Foundation.
Practice areas
Insurance deals and new entrants
Buying and selling insurers and blocks of business, setting up new insurers, bringing foreign insurers into Canada, and licensing insurers and intermediaries.
Pensions, reinsurance and sector agreements
Advising on and drafting pension buy-in and buy-out deals with the reinsurance that supports them, plus outsourcing, distribution and other agreements specific to insurance.
Regulatory compliance and investigations
Advice on the Insurance Companies Act, OSFI guidelines and compliance obligations, along with responding to regulator inquiries and working through investigations.
Education & credentials
- LLB, BCL, McGill University (1987)
- BA (Economics), McGill University (1983)
- Called to the bar of Ontario (1989)
Awards & recognition
- Chambers Canada, Band 1, Insurance: Transactional & Regulatory (Nationwide, Canada), Chambers and Partners
Publications & speaking
- AI-Generated Complaints: Emerging Risks and Compliance Strategies; Federal Updates, CLHIA Compliance and Consumer Complaints Annual Conference, Saint-Sauveur (2026)
- A TPA Receivership: The TruStar Case Study, CLHIA Compliance and Consumer Complaints Annual Conference, Charlottetown (2025)
- Insurance Regulatory Updates and Case Studies, Travel Health Insurance Association of Canada Annual Conference, Palm Springs (2025)
- Regulatory Landscape, Canadian Insurance Accountants Association Annual Conference, Quebec City (2025)
In the community
- Director of the Ladies First Hockey Foundation.
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This listing was generated by AI from public sources in October 2026. It may contain errors, and we can’t guarantee it’s accurate or complete. Before you rely on anything here, verify it on their firm’s website. Confirm Jill E. McCutcheon’s licence and standing in the Law Society of Ontario directory ↗
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