Stephen Billyard is the CEO of Billyard Insurance Group Inc. (BIG). His excellence in leadership is exemplified by BIG’s astounding revenue growth, rapid company expansion, thriving industry partnerships, and numerous accolades. Scaling nationally, he has invested heavily in technology and training to equip teams to reach their full potential. Stephen Billyard was the recipient of the CEO of the Year award at the 2021 Insurance Business Canada Awards, and under his leadership, BIG has received recognition as one of Canada’s Top Growing Companies for 5 consecutive years from 2020 to 2024 by The Globe & Mail’s Report on Business. Insurance Business Canada has also recognized BIG as Big Brokerage of the Year (2022), Fast Brokerage (2023 and 2024), 5-Star Brokerage (2023), and Top Insurance Employer (2023).
Company: Billyard Insurance Group
We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company
Stephen Billyard: Thank you. BIG first began as a family business in my hometown of Welland, Ontario, back in 1991 when it was founded as “Sandy Billyard Insurance Brokers Inc.”. Over time, I saw opportunities to modernize and expand our business offerings, so I purchased the company and re-founded it in 2012. My vision was clear: I wanted to leverage technology to change the face of the digital insurance landscape. Now, in just over a decade, we’ve scaled from a single branch to 85 franchise locations and 1,200 employees across Canada. With technological innovation, we equip our Managing Partners and their teams to do their best work on the technical side while enabling them to maintain exceptional customer service standards.
What were the most significant challenges you faced during the scaling process, and how did you overcome them?
Stephen Billyard: We made some of our biggest strides in scaling during COVID, the volatility of which made decision-making more complex than usual. Navigating uncertain conditions required agility and clear communication with our Head Office teams and franchise partners alike. We ensured everyone understood the evolving landscape and felt supported in their roles. Instead of perceiving the pandemic as a limitation, we seized whatever opportunities it presented to us. As a result, BIG saw unprecedented growth from 2020 onward.
However, as we rapidly scaled, attracting and retaining top talent quickly — and in a competitive job market to boot — was a hurdle. We invested heavily in providing our brokers with comprehensive resources and access to markets that our competitors lacked. That differentiated us. By equipping our teams with excellent tools and support services, we empowered them to excel. In turn, this ensured our growth did not compromise our quality of customer service.
How did you ensure that your company culture remained intact as your business expanded?
Stephen Billyard: People are our number one focus, and that philosophy guides many of the decisions we make here at BIG. “Our people” doesn’t just include our internal teams. It includes our Managing Partners, their employees, our market partners, and especially our customers. I never lost sight of that focus as we grew, and I never will. We want every decision we make to reflect our commitment to our people.
We’ve also always kept vertical lines of communication open across all levels of the organization. I keep my door open to questions, concerns, and ideas as often as I can. In doing so we’ve nurtured trust and interdepartmental collaboration over the years, even during challenging times. By prioritizing transparency, we created a culture where everyone felt informed and valued, and this ultimately strengthened our collective purpose.
Finally, staying true to our core values was instrumental in guiding our actions and preserving the essence of who we are. That said, revisiting those values is also an important part of that equation. Just last month, I surveyed the entire company to get their opinions on our current core values. I want everyone to have a say in what guides us moving forward, not just a few of us in a room at Head Office.
What strategies did you employ to maintain quality and customer satisfaction while scaling rapidly?
Stephen Billyard: We leaned heavily on technological innovation and proactive communication to help our Managing Partners keep up with their businesses at scale. More specifically, we’ve given our brokers advanced AI-based tools designed to enhance their efficiency and effectiveness in servicing their clients. This has yielded consistent service quality despite a heavily increasing volume of business.
We also make great efforts to gather client feedback through our Net Promoter Score (NPS) surveys and Google reviews; we can monitor our performance in real time and address issues and potential escalations promptly. This way, customer satisfaction can stay at the forefront of our focus even alongside rapid expansion.
Can you share a specific turning point that was crucial for your business’s successful scaling?
Stephen Billyard: There was no specific turning point, but some notable decisions over the years have helped us scale. Our franchise model has allowed us to expand our reach to a broader client base, all the while maintaining the flexibility and responsiveness our core business requires. Our technology investments have been pivotal as well. Without them, our front-line broker force and internal teams wouldn’t be able to keep up with their growing workloads. Most importantly, though, hiring the right people to help build the company early on – including our current COO, Cody Douma – has been instrumental in establishing a strong leadership team that drives our vision forward. While our journey has been non-linear, each of those elements has contributed to our resilience and adaptability, positioning us for sustained growth and success.
How did you manage the financial aspects of scaling, particularly in securing funding and maintaining cash flow?
Stephen Billyard: Our franchise model combined with our 100% organic growth have really helped us maintain our cash flow. Franchisees manage their own overhead costs, and this means we have the capital to support them in other ways – loans, training, business support, and more. With our organic growth, we’ve never had to rely on acquisitions, mergers, or massive ad campaigns to attain the growth we have, which is extremely rare in the brokerage space.
Along with this, our investment partnership with Peloton Capital Management has allowed us to be financially agile and focused on our core operations. Our collaboration with Peloton affords us the resources to invest heavily in technology and innovation without compromising our bottom line. These combined strategies have given us a solid financial foundation to support our growth over the years.
