Choosing a career in life insurance sales

by David Keelaghan20 Mar 2017
Selling life insurance may not be the most glamorous of careers, but it is a highly satisfying one according to Dan O'Shaughnessy.

The Cambridge University graduate started his career on the banking side, and at a high level. Roles with Goldman Sachs and Bank of America Merrill Lynch left him with an empty feeling, however, as he outlines.

“When I left Cambridge University, all my friends would talk about banking and consulting, as if those were the only two options,” he says. “Both paid well, opened the door to very challenging problems, and got big names on your CV. Nobody talked about the endless hours, the complete lack of freedom, or the political and dangerous promotion process to the top.”

Wanting to move in a new direction that would fulfill his entrepreneurial ambitions, he established O'Shaughnessy Financial Services. It was a risk for sure, but he was confident he had read the market right and his firm would be providing a much-needed service in the Canadian marketplace.

“When I was deciding what to do for my career, I noticed there was a huge disconnect with the desire for insurance and having the people to service that in the right way,” he says. “A lot of brokers are in their mid-60s.”

At 34 years old, he is part of the new breed of insurance broker that the industry desperately needs. He specializes in term and participating insurance for business owners and professionals who are looking for ways to protect their assets. There still is a great need for this profession, he believes, despite technology offering different options for consumers.

“In the wealth management space, businesses like WealthSimple are doing a great job in marketing their business,” he says. “But there are people where that’s not the kind of environment they want to work in. They want a person to work with and are willing to pay a premium for that.”

While it is generally accepted that the industry has made great strides when it comes to the underwriting process, in O'Shaughnessy’s view the pace of change hasn’t been fast enough.

“Even with technology getting so advanced and people’s expectations being so high, the underwriting process still takes a lot of time,” he says. “To underwrite properly, there’s medical underwriting, then there can be financial underwriting as well. So you’re relying on people, not technology. The current process has not adapted to the times. I’m sure 10 years ago nobody would have minded that length of time. It is still very human driven.”


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