Six insurance organizations have been named among Canada’s Top Small & Medium Employers for 2026, underscoring how a limited group of carriers, MGAs and brokers are reshaping their workplace practices to compete in a tight labor market.
The insurance-sector honorees are CHES Special Risks Inc., Humania Assurance, UV Insurance, Lawrie Insurance Group, One Insurance Group and Trisura Guarantee Insurance. They joined small and mid-sized employers from across the economy in a competition that examines everything from compensation and benefits to training, community involvement and work–life balance.
The annual Canada’s Top Small & Medium Employers list, part of the broader Canada’s Top 100 Employers project, assesses organizations with fewer than 500 employees on HR policies and programs that support staff at different life and career stages.
CHES Special Risks, a managing general agent and wholesale broker founded in 2004, appears on the list for the sixth consecutive year. The Lloyd’s coverholder offers more than 300 commercial products and supports brokers from offices in Toronto, Ottawa, Vancouver, Edmonton, Québec City and Montréal. Its repeat recognition reflects a long-running emphasis on professional development, flexibility and support for employees’ lives outside work.
Humania Assurance and UV Insurance, both Québec-based life and health insurers, bring the perspective of long-established mutual and cooperative players. Their inclusion highlights how regionally anchored carriers can compete with larger institutions on culture, benefits and development, translating member-focused missions into workplace practices such as internal mobility, broad benefits coverage and defined wellness and community programs.
Lawrie Insurance Group and One Insurance Group represent independent, multiline brokerages that have grown to meaningful scale while remaining rooted in local communities – Lawrie with its long history in Ontario, and One Insurance Group with its network across Manitoba. Both have invested in structured training, leadership development and flexible work arrangements to retain experienced brokers and attract new entrants into the profession.
Trisura Guarantee Insurance, a specialty lines insurer, rounds out the group. Known for niche commercial, surety and professional liability offerings, Trisura has built its people strategy around an entrepreneurial culture, clear career paths and a strong emphasis on technical expertise, aiming to give underwriters and claims professionals room to progress within a focused, performance-driven environment.
Across these six organizations, several common threads emerge: structured support for education and professional designations, enhanced parental and family benefits beyond statutory minimums, formal flexible or hybrid work models, and a stated emphasis on inclusion and employee well-being as part of day-to-day culture.
Despite insurance’s scale in the Canadian economy, only a small number of sector employers appear on the 2026 SME list. That scarcity underlines how competitive the awards process has become and how demanding the bar is on flexibility, benefits, culture and career development.
It also suggests that many insurance employers are still adjusting to changing employee expectations. While the industry has traditionally offered stability and solid benefits, formal policies on hybrid work, mental health resources, defined learning pathways and inclusive advancement are now under closer scrutiny from both candidates and external evaluators.
For CHES, Humania, UV Insurance, Lawrie, One Insurance Group and Trisura, inclusion on the list signals that their offerings stand up not only against other insurers, but also against leading SMEs in sectors such as technology, professional services and healthcare.
The recognition comes as Canada’s P&C and life sectors continue to grapple with skills shortages and demographic pressure. Studies point to a large cohort of experienced underwriters, brokers and claims professionals approaching retirement over the next decade, while surveys consistently show relatively few younger workers actively considering insurance as a first-choice career.
At the same time, flexible and hybrid work has emerged as a top non-salary priority for many candidates, and clearer, quantifiable benefits around education, parental leave and mental health increasingly shape how employers are perceived. In that context, documented policies – such as defined tuition support, transparent leave top-ups and explicit hybrid-work frameworks – are becoming nearly as important as base pay in attracting and retaining talent.
The fact that only six insurance-sector organizations made the 2026 SME list points to considerable room for improvement across the broader market. For some firms, that may mean formalizing existing informal practices; for others, it may require more fundamental shifts in how performance, flexibility and support are balanced.
The presence of these insurers on Canada’s Top Small & Medium Employers serves as both recognition and challenge, evidencing that insurance can compete with the best SME workplaces in the country, and a reminder that employers willing to invest in people, culture and modern HR practices are likely to be better placed in the ongoing competition for talent.
