Halpenny Insurance: Poised for Major Growth

Over the last few years, Halpenny Insurance Brokers has been making an impact in the Ottawa region. 

Halpenny, also known as Eastern Ontario’s oldest and largest, locally owned and fully independent insurance brokerage, has roots dating back to 1912 in Westboro. And though that acclaim may give off the impression that Halpenny has an affinity for the traditional, instead, the company has embraced countless changes in its century-long lifespan. 

Its latest change might well be its most exciting.

By Dan Lalande | Photography by Nicolai Gregory


“The Insurance landscape has changed drastically” explains Richard Massie, Halpenny’s enthusiastic CEO. “Many local brokerages have sold. The insurance industry is quite different today than it was a few decades ago. As for our firm, we’ve brought on an entirely new partnership group and a younger generation of insurance experts. We have completed the largest transformation in our history and now have a much stronger core team with an unparalleled depth of experience that will lead our brokerage forward.”

Halpenny’s growth is already evident with its recent rebrand, commemorating its 110 years in the industry. The brokerage also launched a new employee benefits and retirement planning division earlier last year.

“Halpenny can now provide a complete and comprehensive insurance solution to our corporate clients with a high level of expertise and an exceptional service commitment.” its CEO says of the new addition.

Halpenny is no longer just a small brokerage in Westboro is it?

“We most certainly are not!  Halpenny is licensed in every province in Canada and represents all types and sizes of corporate clients from small local businesses to multi-national corporations.”

As a young man, why did you choose insurance?

“After graduating with a degree in Economics from McGill University, I accepted a management training position with Guardian Insurance, a leading commercial insurance insurer at the time. I felt that position would be a great challenge as I entered the business world. I quickly completed my CIP and FCIP designations while working as a commercial insurance underwriter. In March of 1997, Halpenny hired me to grow their commercial insurance division.

After 20+ years of being a partner at Halpenny, I was given the opportunity to take over as President and majority owner in December, 2018.”

 “The last few years have been, by far, the most rewarding in my insurance career. I felt it was very important to personally recruit, interview and hire every new employee. We now have over 50 staff and have integrated seven new partners.”

Poised for Growth: Richard Massie’s Halpenny Insurance is recognized as one of Canada’s fastest growing insurance companies.

The result: Halpenny’s staff doubled during this time period and their revenue tripled, all while successfully negotiating the pandemic. This impressive growth has landed Halpenny recent recognition as one of Canada’s fastest growing insurance companies.

Halpenny seems to be very active in supporting local charities. Can you elaborate on why this is so important to you?

“Giving back to our community is extremely rewarding. We donate to 20-30 local charities every year. It is a very important part of our corporate mission. We live in our community and we care about it and we want to see it flourish.”

Perhaps Halpenny’s biggest attribute and competitive advantage is providing the kind of consulting advice that is essential in today’s risk-strewn landscape. 

“Today’s business owners face an extremely complicated insurance and legal environment. Our risk management and corporate insurance solutions give our clients the guidance and direction they need to manage their businesses without fear of an uninsured loss or lawsuit.”

Looking ahead, Richard emphasizes that Halpenny is poised for major growth and is currently planning further expansion.

Any parting words?

“I would like to hear from and connect with local business owners that are currently not getting expert advice from a locally owned broker. At Halpenny, we are doing things the old-fashioned way.

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