Jill E. McCutcheon

Toronto: 416.865.8121
Fax 416.865.7380


BA (Economics) McGill University LLB and BCL, 1989
McGill University

Bar Admissions

Ontario, 1989


Jill McCutcheon is co-head of the Financial Services Practice. She specializes in insurance - corporate, regulatory and transactional matters. She has more than 25 years of experience in providing 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 is noted for her ability to respond to and resolve issues with the numerous regulators who impact on the insurance sector in Canada. Jill also has extensive experience in privacy law and data breach response matters.

Jill's work includes:

  • Advising on the formation of insurers
  • Advising on governance of insurance companies and advising insurance company boards of directors
  • Obtaining federal and provincial regulatory approvals
  • Resolving distribution, product and other regulatory issues on behalf of clients and with regulators
  • Drafting and negotiating reinsurance, distribution and other specialized agreements germane to the sector
  • Developing policy wordings
  • Advising on reinsurance
  • Advising on self-insured, risk retention and captive strategies
  • Advising on market conduct and compliance requirements
  • Advising on privacy law, the resolution of privacy complaints and privacy breach response


Chambers Canada—Leading lawyer in insurance: transactional and regulatory (2018-2022)

The Legal 500 Canada—Leading lawyer in insurance (2020-2021)

IFLR 1000: The Guide to the World’s Leading Financial Law Firms—Highly regarded in financial services regulatory (2019-2022)

Best Lawyers in Canada—Leading lawyer in insurance law (2021-2022)

The Canadian Legal Lexpert Directory—Leading lawyer in financial institutions regulation - Ontario (2018-2021)

Who’s Who Legal—Leading Canadian lawyer in insurance and reinsurance (2018-2021)

Expert Guides’ Women in Business Law—Leading lawyer in insurance and reinsurance (2018-2021)

Lexology and the International Law Office’s Client Choice Award—Insurance and reinsurance, Ontario and Canada (2014)



Professional Involvement

Jill sits on the Board of Directors of three federally regulated insurers. She serves as Counsel to the Travel Health Insurance Association of Canada and as Director of the Ladies First Hockey Foundation.


Jill sits on the Board of Directors of three federally regulated insurers.


  • Director, Ladies First Hockey Foundation

Memberships and Affiliations

Counsel, Travel Health Insurance Association of Canada