Director, Underwriting Operations, Commercial Mid-Market - West

Job : 10247

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:
Winnipeg, MB;
Vancouver, BC;
Calgary, AB;
Edmonton.

Working Business Language
:
English

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: $180,000 - $200,000. 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 Director, Underwriting Operations, Commercial Mid-Market is responsible for leading Wawanesa's Middle Market Property & Casualty, Agriculture and Fleet teams across Western Canada - driving profitable growth, portfolio diversification, and operational excellence within a nationalized underwriting structure. Focused on larger commercial business, this role provides technical leadership in underwriting, pricing, risk selection, portfolio management, and broker engagement to deliver competitive solutions for mid-sized businesses across Western Canada.

Working closely with the VP, Mid-Market, this leader will help shape the future of Commercial Middle Market at Wawanesa, while leading and coaching underwriting leaders and teams, maintaining a strong market presence with brokers, and advancing strategic priorities. The role holds the highest underwriting authority for the segment, providing expertise and guidance on complex commercial risks and large account opportunities.

• Oversee underwriting processes, workflows, and governance to ensure accuracy, speed and ease of doing business.
• Standardize practices, procedures, and tools across regional underwriting teams to drive national alignment while maintaining regional expertise and broker service models.
• Monitor underwriting performance metrics and operational KPIs, implementing corrective action where needed. Provide oversight of catastrophe-exposed and large complex accounts to ensure strong risk management, underwriting discipline, and portfolio profitability.
• Collaborate and provide input into the design and implementation of the transformation roadmap for Commercial Small Business.
• Move at…