Director, Underwriting Operations, Commercial Mid-Market - West

Wawanesa; Calgary; On-site; CAD 180,000 - 200,000; Full time

Benefits offered by this job

Annual bonus

Pension plan

Generous vacation time

Benefits package

Job summary

The Director, Underwriting Operations, Commercial Mid-Market at The Wawanesa Mutual Insurance Company leads Western Canada's Middle Market Property & Casualty, Agriculture and Fleet underwriting teams to drive profitable growth and operational excellence.

Responsibilities include guiding underwriting, pricing, risk selection, and broker engagement, with the highest underwriting authority for the segment, and shaping the future of Commercial Middle Market across Western Canada.

Qualifications

• 10+ years of experience in commercial insurance, with mid-market underwriting expertise.
• At least 5 years in a leadership role leading regional underwriting teams and broker relationships.
• Bachelor’s degree in business, insurance, risk management, or related field; MBA/CRM/CIP/FCIP assets.

Responsibilities

• Oversee underwriting processes, workflows, and governance to ensure accuracy, speed and ease of doing business.
• Standardize practices, procedures, and tools across regional underwriting teams for national alignment.
• Collaborate on the transformation roadmap for Commercial Small Business.
• Lead and coach underwriting leaders and teams across BC, AB, MB, and SK.
• Build strong broker relationships to support profitable growth.
• Drive risk management and portfolio profitability.

Skills

Leadership

Underwriting

Broker relations

Strategic planning

Education

Bachelor's degree in business/insurance

MBA/CRM/CIP/FCIP assets

Job description

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Director, Underwriting Operations, Commercial Mid-Market - West

Job ID: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.

About The Wawanesa Mutual Insurance Company
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 wawanesa.com.

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.

Job Overview

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.

Responsibilities

• 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 pace by applying a test-and-learn approach, failing fast and pivoting quickly in response to learnings.
• Use effective collaboration and communication with key stakeholders to navigate roadblocks and governance processes.

Empower, mentor, and develop a high-performing underwriting operations team in Commercial Small Business, fostering a culture of accountability, collaboration, and innovation. Provide leadership and coaching to underwriting leaders and teams across BC, AB, MB, and SK.

• Attract and retain top talent, focussing on capabilities that will accelerate the transformation and thrive in the future state.
• Serve as a key liaison between underwriting, distribution, actuarial, claims, finance, and compliance functions.
• Build strong relationships with brokers and partners to ensure service expectations are met and exceeded.Maintain a visible market presence and strengthen strategic broker relationships to support profitable growth.

Qualifications

• Minimum 10 years of experience in commercial insurance, with deep expertise in mid-market underwriting in the specific segment.

At least 5 years in a leadership role, preferably within a national insurer, with experience leading regional underwriting teams, broker relationships, and complex commercial portfolios.

Bachelor’s degree in business, insurance, risk management, or related field. MBA, CRM, CIP, or FCIP are considered assets.

• Product development and portfolio management experience considered an asset.
• Strong understanding of the mid-market business environment, commercial lines regulatory frameworks, and broker distribution models.
• Proven ability to grow income, with a focus on long-term portfolio health, proactively managing risk and building member value.
• Excellent relationship management, communication, and stakeholder engagement skills.
• Bilingualism in English and French is considered an asset.
• Ability and willingness to travel nationally to engage with regional teams and brokers.

Diversity Equity, Inclusion& Belonging

At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.

We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas.

We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to [e-mail] .

Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.