Jill McCutcheon > Torys > Toronto, Canada > Lawyer Profile


Work Department



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 has broad and extensive experience advising on all aspects of activity in the insurance industry. This includes advising on the formation of insurers, governance matters and obtaining federal and provincial regulatory approvals. She also regularly acts as counsel to insurance company boards of directors.

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.


Ontario Bar, 1989


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.

Lawyer Rankings

Canada > Insurance

(Leading individuals)

Jill McCutcheonTorys

Advising on a number of high-value transactional matters, the team at Torys counts among its clients key domestic and international insurers, insurtechs, and reinsurers. Recent highlights include co-head Blair Keefe advising intact on its C$12.3bn acquisition of RSA Insurance Group, and fellow co-head Jill McCutcheon assisting with Cigna’s $6.3bn sale of its life, accident and disability lines to New York Life. On the regulatory side, the team has a growing practice advising large-scale insurance groups on new lines of business and insurtech integration. The practice also acts in contentious cases, from contract interpretation and statutory concerns to matters heard before the Supreme Court of Canada. Other key names include Kelly Morris, who advises on insurance regulatory law with an emphasis on privacy and security, and associate Melissa Prado, who has a transactional focus. All named lawyers are based in Toronto.