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The talent shortfall within the insurance industry and the succession problem we all face need to be urgently addressed. Insurance serves a key societal function in the world economy and is filled with skilled people doing interesting and varied work. If we, as the current industry workforce, don’t accept the challenge of putting this wonderful industry in a better place than when we found it, our clients, employees, companies and reputations will all suffer. I am told that back in the 1980s, there were two industries that topped new business school grads’ wish lists across North America: investment banking, presumably due to the roar of the leveraged buyout and insurance. How different the world is for one of these industries four decades later, where investment banking remains highly desirable by new grads, yet not so for insurance. Somewhere along the line, because of the overwhelming number of insurance jobs that were filled by the baby boomer generation, we didn’t need to
In the midst of shifting insurance market cycles, businesses are often caught between extremes. In a hard market, premiums soar; in a soft market, prices may drop. While stability may be elusive, the demand for dependable insurance products remains constant—businesses consistently seek the best possible coverage. Berkley Canada, a specialty insurance provider, stands out in this landscape. While the industry has seen a renewed reliance on managing general agents (MGAs) during the hard market, Berkley Canada has remained steady. With access to secure, stable, A+ XV-rated paper, it has no need to chase or replace capital. “We bring in skilled underwriters and claims professionals to make decisions for our clients locally—delivering faster, more personalized, and transparent solutions,” says Ashley Beales, Chief Underwriting Officer. With a foundation of underwriting discipline and long-term partnerships, Berkley Canada ensures that clients have access to top-tier coverage—regardless of market conditions. From complex long-tail liability risks to accident, health, and travel insurance, the company serves both Canadian and international clients with precision, expertise, and a deep commitment to care. Organized into industry-specific and product-focused teams, Berkley Canada caters to sectors such as technology, construction, healthcare, and life sciences, while offering specialized expertise in commercial liability, financial lines, professional liability, and environmental coverage. This approach, combined with its customer-centric model, fosters trust— especially among international clients who value Berkley Canada’s long-term commitment. These qualities endure through volatile markets, where the company’s underwriters— armed with both expertise and autonomy—craft policies tailored to the specific needs of each client. The focus on local empowerment further extends to Berkley Canada’s claims team, which has the authority to act. When a fair resolution is on the table, the team can say “yes” immediately. Such agility proves invaluable in time-sensitive settlement negotiations, which is rare in today’s market. For example, a healthcare association received a fully compliant, customized policy within 24 hours when faced with urgent regulatory insurance changes..
In the Canadian Prairies, where tight-knit communities form the backbone of the economy, the importance of local businesses cannot be overstated. Often passed down through generations, these businesses serve as the lifeblood of small towns and rural areas. Yet, as owners approach retirement, the question of succession looms large. Who will take up the mantle and ensure vital services remain rooted in the communities that need them most? Prairie Centre Insurance solves this dilemma by helping residential and farmland owners, along with local commercial businesses, with an exit strategy. This ensures their operations remain functional while preserving the honor, legacy and community presence that the owner worked so hard to build. The steppingstone for this process starts with Prairie Centre Insurance thoroughly reviewing a client’s business. This involves assessing various aspects such as financial performance, operational efficiency and organizational structure. Based on the review, Prairie Centre Insurance collaborates with the business owner to develop a transition plan. This plan outlines the steps to facilitate the transfer of ownership or management responsibilities, while ensuring a smooth transition for all parties involved. Prairie Centre Insurance has had notable success facilitating the purchase of businesses, taking some of the management workload off the owner in terms of administration, accounting, or operations.
Embodying the philosophy of ‘business with a heart,’ Greatway Financial stands out in the insurance landscape as a premier Insurance Managing General Agency (MGA). The firm ensures that Canadians, both native-born and immigrants, have a fair opportunity to kickstart their careers and create a legacy for their families. Its business, encompassing a wide market and currently thriving in the middle market, fostering a family-oriented culture where everyone rises together. Driven by the saying —practice what you preach— the firm guides clients toward a better financial future, considering the uncertainties and longevity of life. In an industry often characterized by sales pitches and product-focused approaches, Greatway focuses on customer-centric services, encompassing life insurance, critical illness protection and other financial tools. Marlon Antonio, CEO, founder, and lead mentor of Greatway, brings over two decades of experience in the insurance industry. Reflecting on his journey, he recognized a prevailing trend where agents focused on selling products rather than genuinely understanding clients' needs. This experience fueled his determination to establish Greatway to provide personalized advice and ensure each customer receives a policy perfectly tailored to their unique circumstances. "We spend one and a half to three hours explaining the policy in detail to the client," Marlon explains. “This ensures they fully understand their coverage, reducing confusion and increase retention of their policies." At Greatway, the approach to service delivery is comprehensive and empathetic. The firm tackles the lack of ongoing support head-on by conducting annual policy reviews and maintaining a rigorous training program for its advisors. This ensures they are well-equipped to serve clients effectively, always adhering to the principle of fair treatment of customers. Investing in Knowledge and Empathy Greatway's success is largely attributed to its people, each with a distinct background and a shared commitment to making a difference. Antonio, who transitioned from a meat cutter and realtor career to insurance out of a desire to make a tangible difference, exemplifies the aspirations of the individuals served by Greatway. One of the Executive Vice Chairman, Eunice Dator, a former nurse turned insurance agent, embodies a lesson she learned from her mom—if you have something good, you must share it, and if you genuinely desire to help others, money will follow. "I used to hold down two jobs. It was challenging and left me with little time for my family. Greatway changed my life, and I've seen it change the lives of thousands of others as well," shares Dator, highlighting the transformative power of Greatway and its focus on helping others. This culture of compassion permeates every aspect of Greatway's operations, creating a supportive environment where everyone can thrive. Similarly, Carol Villarica, the first National Executive Vice Chairman of Greatway, with her background in dentistry, brings a philosophy of sharing blessings and making a difference. Villarica often emphasizes that in her 36 years of living in Canada, she has never encountered an opportunity that can transform lives as quickly as Greatway. She articulates, "The transformation is real. That's why I'm delighted to belong in an organization where everyone is treated equally, with opportunities for all." By prioritizing transparency and simplicity in financial education, these individuals demonstrate their commitment to addressing clients' needs rather than just selling products. This strategy reflects their long-term vision for creating lasting change in the industry. Transformative Success Stories and Cultural Impact Greatway's impact is not measured in terms of profits but by the lives it transforms. The firm takes a holistic approach to insurance, addressing the broader financial challenges clients face, including inflation and rising expenses.
Beth Diamond, Group Chief Claims and Litigation Officer, Beazley
Holly Hollenbeck, JD, CRIS, Regional Vice President, Legal and Contracts, Marsh McLennan Agency
Alex Stonkus, Senior Underwriting Manager, BCAA
Cheryl Muschette, Director, Claims, BMO
Jonathan Schjott, Regional Vice President, Insurance Brokerage, RBC Insurance
The Canadian specialty insurance sector is adapting to advanced risks and technologies while providing tailored coverage, fostering innovation and stability across industries.
The Canadian insurance market has hardened, increasing premiums and scrutiny, requiring businesses to adopt proactive risk management and strategic broker partnerships for coverage.
Rising Demand, Evolving Risks, and the Leaders Driving Change
Specialty insurance, once a niche offering, is now experiencing significant growth in Canada. As businesses confront a surge in complex and emerging risks, ranging from extreme weather events and cyberattacks to supply chain disruptions and regulatory uncertainty, the demand for tailored coverage is rapidly expanding. Industries such as manufacturing, transportation, real estate, and technology are increasingly turning to specialty insurance as a strategic safeguard against high-impact exposures that traditional policies often fail to address. This transformation is being driven by the integration of advanced technologies across the insurance value chain. Digital platforms, data analytics, artificial intelligence (AI), and IoT-enabled devices are enhancing insurers’ ability to assess, price, and manage risk with greater accuracy. Innovative products such as parametric insurance for climaterelated events and customized cyber liability solutions are gaining traction, offering faster claims settlement and targeted protection for clients seeking immediate, dependable support. Despite the sector’s momentum, several challenges persist. A shortage of skilled professionals, especially underwriters and claims adjusters, continues to strain capacity. Regulatory inconsistencies across provinces add operational complexity. Besides, inflationary pressures, rising reinsurance costs, and evolving expectations around ESG and data governance are reshaping underwriting standards and risk appetites. To remain competitive, the industry is investing in digital infrastructure, forming strategic partnerships, and prioritizing the development of talent. By enhancing analytical capabilities, reskilling teams, and improving client engagement, insurers are laying the foundation for long-term resilience. In this edition, we spotlight influential leaders helping shape the future of specialty insurance. Among them is Matthew T. Studley, Chief Operating Officer, Ontario & Atlantic at HUB International. Studley brings deep expertise in risk transfer for sectors such as investment management, fintech, private equity, and cryptocurrency. We also feature insights from Donna Carbell, EVP, Chief Strategy and Impact Officer at Equitable, and Bogdan Laza, Vice President, Strategic Risk Consultant, Commercial Insurance at Brown & Brown. Their perspectives offer valuable guidance for more informed, datadriven decision-making.