Kaitlin’s practice is focused on transfer pricing and cross-border tax matters, supporting clients across the country and different industries with planning, compliance and resolving disputes with the Canada Revenue Agency.
She also has expertise in other areas of international tax, such as the implementation of the global minimum tax in Canada and the hybrid mismatch rules. Kaitlin was previously seconded to the Department of Finance Canada where she worked on legislation relating to international outbound matters.
Kaitlin is a member of the Young IFA Network (YIN) Committee of the Canadian branch of the International Fiscal Association, and is a frequent speaker and writer on tax and transfer pricing topics.
Representative Work
- 5C Group
5C Group in its US$835-million capital raise from Brookfield and Deutsche Bank
- Suncor Energy Inc.
Suncor Energy Inc. in its takeover of day-to-day operations at Syncrude oil sands mining joint venture
- Wheaton Precious Metals in the successful resolution of its transfer pricing appeal to the Tax Court
- A royalty and streaming company in its pending transfer pricing appeal to the Tax Court
- Various Mutual Agreement Procedure (MAP) matters for relief from double taxation
- Various Advanced Pricing Arrangement (APA) matters regarding, among other things, global cost sharing arrangements
- A pipeline company in the successful resolution of its dispute with CRA regarding transaction costs
5C Group in its US$835-million capital raise from Brookfield and Deutsche Bank
Suncor Energy Inc. in its takeover of day-to-day operations at Syncrude oil sands mining joint venture
- Various Mutual Agreement Procedure (MAP) matters for relief from double taxation
- Various Advanced Pricing Arrangement (APA) matters regarding, among other things, global cost sharing arrangements
- A pipeline company in the successful resolution of its dispute with CRA regarding transaction costs
Latest Insights
-
Osler Update March 18, 2025
Transfer pricing in times of tariff turmoil
We examine the intricate relationship between tariffs and transfer pricing, with insight on how protectionist measures impact pricing.
Read more -
Report December 5, 2024
Canadian global minimum tax, digital services tax and other international tax reforms
The international tax landscape has seen substantial and complex changes in recent years, with still more underway.
Read more -
Osler Update July 2, 2024
Dow Chemical and Iris Technologies: Supreme Court rules on jurisdictional issues in tax matters
In this Update: On June 28, 2024, the Supreme Court released its decisions in Dow Chemical and Iris Technologies regarding the respective...
Read more -
Osler Update May 2, 2024
Canadian government moves ahead with Global Minimum Tax Act
Canada’s Pillar Two legislation, the Global Minimum Tax Act, is introduced in Parliament. In their Update, Patrick Marley, Oleg Chayka, Ilana...
Read more
Awards and Recognition
-
Best Lawyers: Recognized as “One to Watch” in Tax Law
-
Completion of the CPA In-Depth Tax Course and CPA In-Depth Transfer Pricing Course
Media Mentions
-
Media Mentions July 16, 2025
Canada will pay the price for cancelling its digital services tax – Bloomberg Tax
In an article written for Bloomberg Tax, partners Patrick Marley and Kaitlin Gray suggest that Canada’s eleventh-hour decision to cancel its...
Read more -
Osler News February 20, 2025
Osler welcomes 14 new partners and three new counsel in 2025
Osler is pleased to announce the addition of 14 new partners and three new counsel across our offices in Toronto, Montréal, Calgary and Vancouver.
Read more
Community Involvement
- Tax Court Assistance Project
Speaking and Writing
Speaking Engagements
2025 CTF Transfer Pricing Conference
Speaker, “OECD Pillar Two / Amount B & Digital Services Tax”, Toronto, February 27, 2025 (with Patrick Marley)
2024 IFA Congress in Cape Town, South Africa
Speaker, Seminar H “Recent Developments in International Taxation” (on Husky Energy decision), Cape Town, October 27-31, 2024
2024 IFA Congress in Cape Town, South Africa
Speaker, YIN Seminar “Tax Certainty in Uncertain Times: A Regional Perspective and Practical Insights on 21st Century Tax Controversy”, Cape Town, October 27-31, 2024
2024 IFA Canada Tax Conference
Speaker, ‘Hybrid Mismatch Rules: What’s Cooking?’, Montreal , May 14, 2024 – May 15, 2024
2023 CPTS Annual Conference
Speaker, ‘Transfer Pricing Dispute Trends and Issues’, June 6, 2024 (with Amanda Heale)
2021 CPTS Annual Conference
Speaker, ‘Current Cases’, June 1, 2021 (with Joanne Vandale)
2018 CPTS Fall Lecture Series
Speaker, ‘Managing Transfer Pricing Audits and Disputes Pre-Litigation’, October 3, 2018 (with Amanda Heale)
Published Work
“Canada Will Pay the Price for Canceling Its Digital Service Tax”, Bloomberg Law, July 15, 2025 (with Patrick Marley)
“MEGlobal Canada ULC: What Goes Up Must Come Down—Maybe”, International Tax Highlights, May 2025 (co-authored with Amanda Heale)
“Trump’s Plan to Exit OECD Deal Threatens Two Canada Tax Rules”, Bloomberg Law News, February 18, 2025 (co-authored with Patrick Marley)
“Canada’s Double Court System for Tax Challenges Needs Reforming”, Bloomberg Law News, July 30, 2024 (co-authored with Amanda Heale)
“Transfer Pricing 2024 – Canada”, Global Practice Guides, Chambers and Partners, April 11, 2024 (with Edward Rowe, Mark Brender and Amanda Heale).
“Proposed Changes to Canada’s Transfer Pricing Rules” Tax Litigation Journal, Volume XXVI, No. 3, 2023
“Finance Proposes Tying Transfer-Pricing Rules to OECD Guidelines” Canadian Tax Focus, 13:3, August 2023
“Osler Submission to Department of Finance re Finance Consultation Paper on Reforming and Modernizing Canada’s Transfer Pricing Rules”, July 28, 2023 (contributor)
“Canada’s New Transfer Pricing Proposal Likely to Face Criticism”, Bloomberg Tax, Tax Insights & Commentary, July 5, 2023 (co-authored with Amanda Heale and Peter Macdonald)
“TPM-02R: Transfer-Pricing Secondary Adjustments and Repatriation” Canadian Tax Focus, 11:1, August 2021
Credentials
Education
- University of Calgary, J.D.
- University of British Columbia, Bachelor of Kinesiology
Languages
- English
Professional Affiliations
- International Fiscal Association
- Canadian Tax Foundation
- Canadian Petroleum Tax Society
- Law Society of Alberta