75 Years with Halpenny Insurance Brokers

As the insurance landscape evolves, so has Halpenny — a brokerage that balances tradition with forward-thinking growth. Richard Massie shares how the business has expanded its reach, diversified its services and continued to lead with a client-first approach.  

How has Halpenny evolved over the years? 
What began as a very small firm in Westboro Village in Ottawa is now a multi-division firm serving clients across Canada. Percy R. Halpenny founded the brokerage in 1912 — we became an IBAO Member in 1950. Halpenny quickly became a trusted name and pillar of the community. We grew from a local business to a full-service operation including Commercial insurance, Group Benefits and a Private Client division.  

What are the achievements you’re most proud of? 
In 2019, Richard Massie became our CEO and Principal Broker and strengthened our leadership team to position the firm for long-term growth. In 2020 we secured a standing offer with the federal government, expanding our footprint in the public sector. In 2022 we were named one of the Fastest Growing Insurance Brokerages in Canada. In 2023 we launched our Group Benefits division as part of a broader plan to diversify our services. And this year we’re expanding with a new downtown Ottawa office and our first Toronto office, continuing our commitment to long-term, sustainable growth across Eastern Ontario. 

What’s driving the expansion? 
It reflects the scale and structure needed to support a growing business. Our new offices are designed to better support our clients and team. As our Commercial and Benefits divisions grow, we’re building the right infrastructure to ensure consistent service across all regions. The move to downtown Ottawa and our first Toronto office has helped strengthen client relationships while attracting and retaining top talent.  

How is Halpenny supporting Ontario’s broker community? 
Through mentorship, collaboration and advocacy, we continue to strengthen the broker channel and support its growth in Ontario. We encourage our staff and partners to volunteer locally with the Ottawa Insurance Brokers Association (OIBA) — many have served on its Board and Executive Team. We’re also actively involved in training the next generation of brokers. We’re working on partnerships with local educational institutions to create more insurance programs in the area.  

What trends have shaped your approach over the years? 
We've streamlined our systems and increased digital accessibility while ensuring our service level remains above industry standards. We’ve seen an increased demand for specialized insurance products and solutions — we're focused on continuous training, strengthening our team's expertise and recruiting leading talent. The importance of data and compliance has also grown, prompting us to strengthen internal processes. These trends have inspired us to be more proactive, responsive and forward-thinking in how we deliver our services. 

There’s been a shift in client expectations, with a growing desire for faster responses, clearer communication and more control over policies. 

What role do you envision Halpenny playing in the evolving insurance landscape? 
We’re focused on scaling with intention. Our goals include expanding our Commercial, Risk Management and Private Client divisions for high-net-worth clients. We’ll also continue expanding our Employee Benefits division and individual Life and Retirement Solutions division. As we grow, we remain focused on our values of trusted advice and a client-centric approach. Our priority is to stay connected to our clients, introducing new technology to improve their experience. We’re your trusted insurance specialists, delivering customized risk management and insurance solutions with the personal touch that defines our business.