Fraser Reid.

• Position: Teekay Shipping (Canada - Interview

"It's for tax reasons."

You've heard that expression before. For Fraser Reid, vice president, taxation, at Teekay Shipping (Canada) Ltd., it was a turning point in his career.

Here's how Reid explains it: "When I was completing my thirty months of articling for my chartered accountant (CA) designation in the 1990s, there used to be a requirement to complete a significant number of audit hours. Often when on a large company audit, there would be a complex organizational structure for the client's business, and when you asked questions around the office hoping to better understand the structure and related transactions, the response was typically, 'It's for tax reasons.' I wanted to really understand what drove the rationale for these structures--especially for cross-border business transactions. I thought it was a way to add value to both myself as a professional as well as to potential clients. That's when I decided to pursue training in international tax."

Black-Letter Law

Reid finds several aspects of corporate tax law interesting, including tax treaty interpretation, but atop his list is how a specific word in "black-letter law" may have a deep, below-the-surface meaning that requires a tax specialist to understand both the context from the perspective of the drafting of the particular area of law as well as how the word has been historically interpreted in previous jurisprudence. "Occasionally," Reid explains, "this can play a significant factor in assessing the tax position of a business transaction that is within the purview of this specific tax law."

Anti-Avoidance Rules

What's the most problematic tax law problem Reid has encountered in his career? "One very challenging area is anti-avoidance rules--especially if you're assessing a transaction that has both bona fide commercial reasons as well as a tax benefit attached to it. Knowing where the fine line in the sand might be on when a transaction facing these circumstances is likely to be OK from a tax perspective as opposed to when it could be viewed as tax-motivated can be a tricky concept to accurately assess," he says.

OECD BEPS Initiatives

The corporate tax area always holds surprises. For Reid, the biggest has been how quickly the OECD BEPS initiatives are getting traction since the guidance was released in 2013 and how rapidly various jurisdictions are implementing these concepts in their respective domestic tax laws. "Although tax practitioners were aware of the fundamental...