By: Billyard Insurance Group
In a dynamic conversation with Stephen Billyard, the CEO of BIG, he reveals the driving forces behind his leadership style, his strategies for fostering high-performing teams, and his vision for BIG’s future in the Canadian insurance industry. With a focus on technology, culture, and resilience, the CEO provides valuable insights into navigating challenges, making tough decisions, and inspiring a thriving workplace.
Q: How would you describe your leadership style?
“My leadership style is transparent, proactive, value-driven, and empowering. If I’m not honest with my team down to the last broker, I’m not doing my job right. I also believe in giving people the autonomy to make their own informed decisions. I trust their judgment but always offer guidance and clarity. In times of uncertainty, I work hard to keep calm and optimistic so my team feels stable, prepared, and motivated to achieve our goals together. Ultimately, it’s not just for BIG’s benefit, but for their own growth and success.”
Q: How do you build and motivate high-performing teams?
“Building high-performing teams starts with hiring the right people who are both talented and aligned with our culture. I believe in empowering our leaders by giving them ownership of their projects and maintaining open communication. I hold regular town halls to share my thought process so they can see the broader vision of BIG and feel equipped to contribute meaningfully. That shared understanding goes a long way in building trust and fostering motivation.”
Q: Can you share an example of a time you had to make a difficult decision and how you navigated that situation?
“There was a critical point where we had to choose between scaling rapidly or investing heavily in a new technology that could disrupt our operations in the short term. I chose to prioritize long-term innovation over immediate growth, a decision that was not easy due to the risks involved. But I felt that building our AI-driven underwriting tool, Precision would be transformative for BIG. It’s one of the important decisions we’ve made. Precision has given us an edge in the market and opened doors to even more sophisticated tech projects that will define our future.”
Q: How do you continue to develop your leadership skills?
“I’m constantly looking for learning opportunities. Courses, seminars, and mentorship from seasoned industry leaders are invaluable to me. I also prioritize self-reflection, making it a point to evaluate my own performance regularly and listen to feedback from my team. This introspection is crucial for me to evolve as a leader and ensure I’m always improving.”
Q: What are the most important lessons you have learned in your career?
“There are two guiding principles I always follow: resilience is king, and adapt or die. Resilience and adaptability have allowed BIG to succeed even in challenging times. As a CEO, I’ve learned the importance of delegating and trusting my team. Without that trust, you’ll constantly feel like there isn’t enough time in the day. Finally, taking care of my mental and physical health has become a priority. If I’m not at my best, then BIG won’t be either.”
Q: What advice would you give to aspiring CEOs?
“Focus on your people and culture, especially as your business scales. Technology and innovation are essential, but without the right team and environment, even the right tools won’t reach their full potential. Be both a visionary and a creative problem solver and never stop adapting as your company evolves. Reinventing your approach as a leader is part of being introspective and essential to staying effective as your business changes.”
Q: What are your thoughts on the current state of the insurance industry in Canada?
“We’re in a hard insurance market here in Canada, and on the brokerage side, there are new regulatory demands, shifting consumer expectations, and external crises affecting us. The industry has been slow to adopt new technologies, but I believe that those who embrace innovation will thrive. For BIG, technology is at the core of how we stay competitive and responsive to these demands.”
Q: How is BIG different from other insurance companies?
“At BIG, our focus on technology and innovation is central, but our culture is what really sets us apart. We empower our brokers with excellent tools and the freedom to excel. We’re agile enough to pivot quickly in response to market changes while maintaining our commitment to evolution and innovation. It’s a balancing act, but it’s one we’re committed to upholding.”
Q: What are your plans for growing BIG in the coming years?
“We’re looking to grow a sustainable and profitable book of business. Expansion into British Columbia is on the horizon, along with strengthening our presence in Alberta and the Atlantic provinces. Ultimately, we’re focused on growth that aligns with our standards for quality and innovation.”
Q: What are the biggest challenges BIG is facing?
“Our biggest challenge right now is the tough market conditions, especially with the auto theft crisis in Ontario. Finding the right quantity and quality of seasoned professionals to meet our expanding needs is also challenging. We’ve built full teams to support our evolving operations, but we’ll need to continue hiring in the coming months to keep up with demand.”
Q: What are your thoughts on the role of technology in the insurance industry?
“Technology is no longer optional; it’s a necessity in our industry. Whether it’s combating fraud, driving operational efficiency, or enhancing customer experiences, tech enhances every aspect of our business. At BIG, technology has allowed us to scale without sacrificing quality or control, and that’s something I’m really proud of.”
Q: What advice would you give to someone who is looking to buy insurance in Canada?
“My advice is to work with a broker who understands your needs and make sure you fully understand the coverage you’re purchasing. Double-check that no essential coverage was removed just to lower the premium if you’re comparing quotes. Also, make sure your personal information is accurate to avoid future issues, and only sign your policy after a thorough review.”
Q: What are your thoughts on the future of the insurance market in Canada?
“I think we’re going to see significant change, with technology playing a central role. Digital innovation will result in improvements in service and overall outcomes. The industry will also diversify as more people move to Canada, bringing new perspectives. However, we also have to brace for the challenges of environmental disasters, which will continue to impact market conditions.”
Q: What are your proudest accomplishments?
“I’m incredibly proud of the leadership team we’ve built; BIG would not be where it is without each one of them. Recently, I’d say building Precision is a major accomplishment, as it’s now the backbone of our operations. And receiving recognition, like being named in The Globe and Mail’s Top Growing Companies list and the CEO of the Year award from Insurance Business Canada, are milestones that hold special meaning for me.”
Q: What are your biggest goals for the future?
“My main goals are to expand into other provinces and eventually take BIG public. I want BIG to be Canada’s most trusted and reliably growing brokerage, delivering high-quality business to the market while offering our customers high-quality service.”
Through this candid look at his journey, the CEO offers valuable insights into his approach to leadership, technology, and building a resilient, forward-thinking company. His unwavering focus on innovation, strong team culture, and adaptability serve as a roadmap for BIG’s continued success in the Canadian insurance industry.
Published by: Josh Tatunay
