Stephen Cheeseman, CIPP/C


Thinktum Inc

Legal and Compliance Attorney

For 25 years, Stephen Cheeseman has brought legal and compliance experience to financial services and technology-driven companies throughout North America. This includes 20 years in legal and compliance leadership in Canada and the US, and includes tenure with Foresters Financial, HSBC, Canada Protection Plan, and Mutual Life. He currently sits in advisory and committee roles for the Ontario Bar Association, the Canadian Corporate Counsel Association, the IAPP, the American Bar Association Cyberspace and International Law Committees and the Society of Corporate Compliance and Ethics.


Mr. Cheeseman is admitted to practice law in Canada, the US, and the UK. He has held roles as a FINRA Certified Compliance Officer, a Canadian Securities Institute-qualified Chief Compliance Officer, an IAPP Certified Privacy Officer, an ACAMS Certified Anti-Money Laundering Officer, and is a qualified Certified Cryptocurrency Investigator.


As a respected subject matter expert, Mr. Cheeseman has published works on a range of technical topics, including: the intersection of technology and regulation, financial services privacy standards, and the global growth of the Regulatory Sandbox concept. He is also an enthusiastic educator and has taught in the financial services sector, and presented on both online and terrestrial radio platforms on regulating technology.


His current role as Head of Legal and Compliance for thinktum, inc. places him at the forefront of Canadian and American intellectual property, privacy laws, and provides corporate direction as to how thinktum’s technology will impact insurance underwriting platforms.


Mr. Cheeseman is an active sports enthusiast and coach, including playing and coaching hockey and introducing youngsters aged 3-5 to the sport of downhill skiing.


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Contributions by Stephen Cheeseman

  • Member of Canadian Advisory Board 2020 - 2023