With new downtown offices now open in Ottawa and Toronto, Halpenny Insurance Brokers enters its next phase of growth—rooted in legacy and driven by leadership.
At a time when many businesses are scaling back, Halpenny Insurance Brokers is doing the opposite—growing, expanding, and doubling down on its presence in the nation’s capital.
This spring, the company opened its doors to its newest location: a bright, modern office in the heart of downtown Ottawa, designed to reflect both its deep local roots and national reach.
Bright and open with views of downtown Ottawa, Halpenny’s new office reflects the company’s forward momentum and modern approach. | Photography by Nicolai Gregory
With over 110 years of history, Halpenny is Eastern Ontario’s largest independently owned brokerage. The company offers commercial insurance, employee benefits, private client services, group and affinity insurance, and risk management services. Licensed across Canada, its client base spans sectors and cities—but its approach remains distinctly personal.
“We are entrusted by our clients to manage and protect their operations, assets, and people,” says Richard Massie, CEO. “We’re not just here to sell insurance—our brokers are trained to understand our clients’ needs, assess their exposures, and design and implement insurance programs that protect every facet of their organization. Our brokers are not sales-focused. They are all leading insurance experts, extremely well-trained to identify risk, well-versed in insurance wordings, and know how to structure policies that will help protect our clients should a serious loss occur. That is the Halpenny difference!”
In recent years, Halpenny has more than doubled its staff and expanded into new markets. At the heart of that growth, says Massie, is their exceptional team. “Our employees are our biggest strength,” he explains, “and that experience is what drives us forward.”
Heritage remains a key part of Halpenny’s identity. Many clients have stayed with them for decades—some for over 50 years. That loyalty, Massie says, speaks to the way the company builds relationships.
“We’re constantly evolving, especially as the industry changes,” he says. “But while we embrace innovation, we stay grounded in our roots. Our history, our relationships, and our reputation are our strength.”
That balance—between evolution and legacy—is reflected in the company’s newest space. Opened in May 2025, the downtown Ottawa office marks a bold step forward, especially at a time when many businesses are moving away from the core.
“We strongly feel Ottawa needs to continue revitalizing its downtown,” says Massie. “We’re proud of this city, and when our clients and industry partners visit, we want them to see that pride reflected.”
More than a location change, the new office signals a renewed energy. “It’s a modern space that reflects our passion and commitment,” Massie says. “It also gives us the perfect venue to connect with clients in person. There’s a great atmosphere here—we hope people drop in and feel it for themselves.”
Since taking over the company in 2019, Massie has led Halpenny through major change—including a global pandemic. “We were in the middle of transforming our operations when COVID hit,” he recalls. “But we didn’t slow down. If anything, it gave us even more clarity. We expanded our team during those years—it was a pivotal time.”
That momentum continues. Alongside the Ottawa office, Halpenny is now expanding into Toronto.
“Toronto is Canada’s largest market, so having a presence there is key to our growth and success,” says Massie. “We already serve many clients in Eastern Ontario, and building a local team in downtown Toronto ensures we service these clients properly and with a personal touch.”
Through all of this, Massie says the company’s focus remains simple: trust. “It’s our biggest responsibility,” he says. “When I see our client base growing, that’s the strongest sign we’re doing something right.”
Leading Halpenny into this new era, Massie keeps his focus on the people behind the progress. “Building and leading this team has been the most rewarding part of my career,” he reflects.
As Halpenny enters its next chapter, one thing is clear: growth hasn’t changed what matters most. The new office is more than a modern space—it’s a reminder of what’s possible when a company keeps showing up for its people, its clients, and its city.
