Heads Up

By broadening his perspective, Ryan Caughey landed in the general counsel position at Sentry Investments, where he gets to see the larger effects of his work

Ryan Caughey
“Sentry is poised to have a long and successful future, and I’m certain that’s because of the galvanizing experiences [its executive team has] had together.” —Ryan Caughey, General Counsel
For a simple sports analogy, “keep your eye on the ball” is usually pretty sound business advice, no matter what your role or industry may be. And it might have held true for attorney Ryan Caughey, too—at least 10 years ago. But the expression also indicates a myopia that will only get a professional so far, so when Caughey discovered he wanted to be not just a counsel but rather a partner to his clients, he decided he needed to widen his view.

Before Caughey became the general counsel for Sentry Investments, he spent his formative years like most junior attorneys: reviewing documents, reporting potential liabilities, and gaining the technical chops to counsel his own clients. “Think of it as being a guy on an assembly line,” Caughey says. “You do you little piece and are oblivious to what the finished product looks like.”

Even after Caughey became more senior at Osler, Hoskin & Harcourt LLP—where he started his career and developed a reputation for his work on large mergers and acquisitions—when a case was closed, so too was any opportunity for follow-up or ex post facto advice. “Many files would be one-off situations, so I would do my bit but rarely be privy to all of the information about the client I’d like to have had,” Caughey says.

It wasn’t until he took a secondment to the Ontario Municipal Employees Retirement Systems (OMERS) that he got a taste of the exclusivity that in-house counsel work offers. “Everything I did was directed towards that single client, where you could see your contributions in action,” Caughey says of the case. “It provided [me] more satisfaction as a lawyer because I could see how my work fit into the larger picture of that business.”

It was the appeal of that dynamic that encouraged Caughey to look outside private practice and into the legal department at Sentry. The investment company piqued his interest while he was working in private practice on a lengthy transaction involving one of Sentry’s competitors. The experience provided Caughey with insight into the inner workings of investment fund companies and the industry in general. When the opportunity to join Sentry presented itself, Caughey jumped at the chance to leverage his previous experience and add value to an up-and-coming industry player.

DOs & DON’Ts

Succeeding as a General Counsel in the Financial Industry


Be open to new ways of doing things.

Ensure that the right minds (not titles) are in the room on key decisions.

Practice strategic relationship management.

Actively communicate with key stakeholders.

Have the courage and conviction to speak your mind.


Be afraid to delegate.

Succumb to hubris. Stay on your toes at all times.

Forget to provide feedback and praise.

Be afraid to have tough conversations.

Take things personally. It’s just business!

“At the time of my arrival, Sentry was very active in creating closed-end investment trusts, and I really enjoyed the transactional side of things,” says Caughey, who became immersed in the business, helping its newly appointed general counsel get the basics of the legal and compliance department up and running. Then, after that attorney left to start his own firm, Caughey took the reins as general counsel and, together with a group of other executives, went to work reinventing Sentry after it fell on hard times during the market downturn of 2008 and 2009. Through hard work and determination, Sentry transformed its fund lineup from primarily closed-end offerings to the well-rounded suite of mutual funds it offers today. “The timing was perfect,” Caughey says. “The rebirth of the company came about during a critical transition for me personally, so, in many ways, our development was simultaneous.”

While Sentry’s identity has become clear in the past four years, Caughey continues to develop his leadership skills because he’s always striving to be a better executive. With the help of Sentry’s executive coaching program, he is on his way. And, he says, his membership and participation in various industry associations has been a tremendous asset.

Though he doesn’t have a formal business background, Caughey’s mutual fund acumen is increasing on the job. “As I continue to refine my understanding of all aspects of the business, I’ve become a much stronger contributor to the strategic direction of Sentry,” he says, and he notes that the rest of Sentry’s leaders are rich with potential, too. “We’re a very young executive team. We’ve been together and have grown as a group. Sentry is poised to have a long and successful future, and I’m certain that’s because of the galvanizing experiences we’ve had together.”