The CN Tower had been open just three years when Dennis Craig first walked into the North American Life regional office across the street. It was the fall of 1979, and the young University of Toronto graduate had signed on for a two-year training program. Four and a half decades later, Craig is calling it a career.
“I love the business,” he said in an interview on Tuesday. “It’s a really nice environment to work in.”
Craig accepted a marketing role at New York Life as it was building its group business in 1986.
“My boss asked me to spell group,” he said. “I said G-R-O-U-P. He said, ‘good, you’ve got the job.'”
It was an opportunity to learn a part of the business he’d never worked in, from the “ground up,” Craig said. It would be a recurring theme in his career. He went on to lead the marketing team at Gerling Global Life Insurance in 1989, and then join Westbury Life as senior vice-president, sales management in 1997. That was just a year after it had been acquired by RBC.
While Craig had studied commerce and economics at university, it was this jump-in-the-deep-end approach that turned him into one of the Canadian industry’s most knowledgeable leaders. I saw this up close when he and I worked together at RBC Insurance. Craig knows nooks and crannies of the business that most of us have never heard of.
He did, after all, see the modern Canadian industry grow up in real time. He remembers premium payments being recorded by hand on client cards that had 52 tiny boxes — one for each week. “That was a challenge for me because I couldn’t write that small.”
Craig was working out of a North American Life branch in 1980 when the first IBM 3270 PC arrived. It connected mainframe computers to an individual workstation. It ran Lotus 1-2-3 off of an Intel 8088 processor, complete with floppy drives.
“Everybody was afraid that they might break it,” he said. No wonder. The team was warned not to spill anything on the unit’s $800 keyboard.
Craig was 23, and less apprehensive. He remembers printing a client list for an advisor from Windsor with about 4,700 names on it. “I didn’t realize the printers weren’t very fast,” he said. “I had to sit there for hours.”
Desktop PCs, laptops, the internet, social media and now AI — they all rolled out under Craig’s watch. The business grew, it demutualized and consolidated. Markets climbed, corrected and even crashed. He saw it all.
Craig’s decision to retire at 69 reflects more than just an affection for the industry. The other thing that’s changed during his working life is the nature of retirement. Gone are the days when the average Canadian called it quits in their early 60s. Like so many, he understood the health benefits of work and the advantages that come with an active life.
Craig and his family have a new golden retriever to ward off a sedentary post-work lifestyle. Teddy is six months old and a healthy 58 pounds. “I want to stay active,” he said.
I reached out to a couple of Craig’s colleagues for reaction to his retirement. Their praise for him was effusive. I’ll give the last word to Michael Hamilton, senior vice-president and chief distribution officer at RBC Insurance.
“Dennis Craig has been a cornerstone in our industry,” Hamilton wrote me in an email. “He is viewed as a trusted advisor on all things insurance related, and is able to approach all discussions in a candid, honest fashion … He is one of the greats.”
Join us May 12 for the kick-off of our Advisor Learning Series. This one’s focused on alternative investments — private markets, real assets, liquid alts and more. Online and in-person at 150 King St. W.