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. 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. 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 advantages 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. About The Wawanesa Mutual Insurance CompanyFounded 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. 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. Job OverviewThe 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 underwriters to undertake competitive research, develop solutions, identify opportunities, and ensure portfolio quality, and profitability while maintaining a competitive edge. This role will hold high underwriting authority for the business segment and provides technical leadership and coaching to underwriters to get complex deals over the line.



Support the development of underwriting playbooks for the defined mid-market segment, ensuring the portfolio is positioned for profitable growth, operational excellence, and superior service. Support the development of underwriting standards, tools, pricing strategies, and risk management practices tailored to the complexity and scale of the specific segment. Act as a technical expert for the specific segment, this will include supporting the underwriting of large accounts, performing file reviews, large loss analysis, portfolio reviews and coaching underwriters while holding high underwriting authority for the business segment. Collaborate with actuarial, analytics, and data teams to ensure pricing reflects risk exposure, competitive benchmarks, and emerging trends in the mid-market segment. Partner with product development teams to evolve mid-market offerings, introducing solutions that respond to broker and member needs and drive profitable growth Working closely with Risk Preventions Services and Claims teams to drive compelling member propositions, solution and efficiencies enabling brokers to sell Wawanesa as a market of choice. Support the director in providing technical leadership to middle market underwriters fostering a high-performance and purpose-driven culture that drives profitable growth while driving underwriting quality and pricing adequacy. Ensure the portfolio is underpinned by sound governance, underwriting discipline, and compliance with all applicable regulatory and corporate policies. Align operations and underwriting guidelines with claims strategies to drive consistent outcomes and ensure fair, member-centric experiences. Support the director in monitoring and reporting on key portfolio performance met

📌 Bilingual Farm Underwriting Specialist, Commercial Mid-Market (Winnipeg)
🏢 Wawanesa Insurance
📍 Winnipeg