Bilingual Farm Underwriting Specialist, Commercial Mid-Market

Job : 10248

Employment Type: Existing Role

Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations:
Toronto (North York), ON;
Kitchener, ON;
Ottawa, ON;
Montreal, QC;
Quebec City, QC, Moncton, NB;
Dartmouth; NS.

Working Business Language: Bilingual in French and English. This role requires regular interaction with customers across Canada, including in Quebec, where the business languages utilized are both English and French. As such, the successful candidate must be fully proficient in English and French.

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan.

The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $120,000 - $145,000. Candidates with salary expectations outside of the range are still encouraged to apply.

Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance.

In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.

Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at

We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.

The Segment Specialist, Commercial Mid-Market is responsible for working closely with the Director, Underwriting Operations, Commercial Mid-Market to drive Wawanesa’s strategy, performance, and execution for the national [insert segment] portfolio. Targeting commercial policies ranging from $10K to $500K in premium, this role is responsible for developing underwriting playbooks, analyzing performance, identifying growth and product development opportunities for the defined mid-market business segment, and provides national technical leadership in underwriting, product development, pricing, risk selection, and quality assurance for the specified segment, ensuring portfolio quality, profitability and competitiveness for the defined segment/portfolio.

Reporting to the Director, Underwriting Operations, Commercial Mid-Market this creative, solution oriented, technical underwriter works close partnership with middle market…