With extensive experience and nuanced knowledge of the complex regulatory landscape of the insurance industry, Jill gives clients practical advice on regulatory, transactional and other advisory matters.
Co-head of the firm’s Financial Services practice, Jill has more than 25 years of experience advising the property and casualty, life and reinsurance sectors of the insurance industry on corporate, regulatory and transactional matters.
Jill regularly advises on all aspects of the law, whether federal or provincial, and acts as counsel to a broad range of clients, including insurers, reinsurers, banks, credit unions, intermediaries, cover holders and MGAs, third-party administrators, retailers, employers and associations. Jill is noted for her ability to respond to and resolve issues with the numerous regulators who impact on the insurance sector in Canada. She also has extensive experience in privacy law and data breach response matters.
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
She frequently engages with regulators, resolving distribution, product and other regulatory issues on behalf of her clients. Jill also counsels clients on market conduct and compliance requirements.
Her work regularly involves drafting and negotiating reinsurance, distribution and other specialized agreements germane to the sector, developing policy wordings, and advising on reinsurance and self-insured, risk retention and captive strategies.
Beyond insurance matters, Jill has experience in privacy law, the resolution of privacy complaints and privacy breach responses.
2018-2025 | Chambers Canada—Leading lawyer in insurance: transactional and regulatory |
2020-2024 | The Legal 500—Leading lawyer in insurance |
2019-2023 | IFLR1000: The Guide to the World’s Leading Financial Law Firms—Highly regarded in financial services regulatory |
2021-2025 | Best Lawyers in Canada—Leading lawyer in insurance law |
2018-2023 | The Canadian Legal Lexpert Directory—Leading lawyer in banking and financial institutions regulation (Ontario) |
2018-2022 | Who’s Who Legal— Global and National leading lawyer in insurance and reinsurance |
2018-2022 | Expert Guides’ Women in Business Law—Leading lawyer in insurance and reinsurance |
2014, 2022 | Lexology and the International Law Office’s Client Choice Award—Insurance and reinsurance (Ontario and Canada) |
Jill sits on the Board of Directors of three federally regulated insurers. She also serves as Counsel to the Travel Health Insurance Association of Canada and as Director of the Ladies First Hockey Foundation.