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About the Role

The Segment Specialist, Middle Market Commercial Insurance will collaborate closely with the Director, Underwriting Operations, Middle Market Commercial Insurance to drive Wawanesa's strategy, performance, and execution of the national portfolio. Targeting commercial insurance policies with premiums from $10,000 to $500,000, this role is responsible for developing the underwriting strategy framework, analyzing performance, and identifying growth and product development opportunities for the defined middle market business segment. This role will also provide national technical leadership in underwriting, product development, pricing, risk selection, and quality assurance for the specified segment, ensuring the quality, profitability, and competitiveness of the defined segment or portfolio.

Responsibilities

Participate in the development of underwriting manuals for the defined middle market segment, ensuring the portfolio is positioned for profitable growth, operational excellence, and superior service.
Contribute to the development of underwriting standards, tools, pricing strategies, and risk management practices tailored to the complexity and scale of the segment.
Act as a technical expert for the target segment, supporting the underwriting of major accounts, conducting file reviews, analyzing significant claims, and performing portfolio reviews, while mentoring underwriters and holding high underwriting authority for this business segment.
Collaborate with actuarial, analytics, and data teams to ensure pricing remains competitive and reflects risk exposure and emerging trends in the middle market segment.
Partner with product development teams to evolve middle market offerings, introducing solutions that meet the needs of brokers and members, and driving profitable growth.
Work closely with risk management and claims teams to provide compelling and effective solutions to members, enabling brokers to position Wawanesa as a preferred choice in the market.
Support the Director in providing technical leadership to middle market underwriters, fostering a high-performance, goal-oriented culture that drives profitable growth while promoting underwriting quality and pricing adequacy.

Requirements

At least 10 years of experience in commercial insurance, with in-depth expertise in middle market underwriting within a specific segment.
Strong communication skills in both French and English, oral and written.
Bachelor's degree in Business Administration, Insurance, Risk Management, or a related field. An MBA or Canadian Risk Management (CRM) designation is a significant asset.
FCIP or CIP designation.
Experience in product development and portfolio management is an asset.
Solid understanding of the middle market, commercial insurance regulatory frameworks, and broker distribution models.
Proven ability to balance growth and risk, with a focus on long-term portfolio health and member value.
Excellent relationship management, communication, and stakeholder engagement skills.
Bilingualism (English and French) is an asset.
Ability and willingness to travel nationally to collaborate with regional teams and brokers.

Skills

Underwriting strategy
Performance analysis
Product development
Risk selection
Quality assurance
Pricing strategies
Risk management
Competitive analysis
Business development
Portfolio management
Relationship management
Stakeholder engagement

Location

Toronto (North York), ON
Kitchener, ON
Ottawa, ON
Montréal, QC
Ville de Québec, QC
Moncton, NB
Dartmouth, NS

Work Type

Hybrid
Full-time

Experience Level

10+ years of experience in commercial insurance
In-depth expertise in middle market underwriting

Education Level

Bachelor's degree in Business Administration, Insurance, Risk Management, or a related field
MBA or Canadian Risk Management (CRM) designation is an asset
FCIP or CIP designation

Salary/Compensations

$120,000 - $145,000

Benefits

Annual incentive program
Supplementary leave programs
Generous vacation days
Personal days
Bonus-free benefits
Pension plan

About the Company

Founded in 1896, Wawanesa Mutual Insurance Company is one of Canada's largest mutual insurance companies, wholly owned by its members, with over $4.1 billion in annual revenue and $12.5 billion in assets.
Wawanesa, headquartered in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance solutions across Canada, and Western Financial Group, a major national distributor of personal and business insurance.
In March 2026, Wawanesa entered into an agreement to acquire The Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.
Wawanesa is proud to serve over 1.8 million members and employs over 3,000 people across Canada.
The company actively gives back to organizations that strengthen communities, donating over $4 million annually to charities, including over $2 million annually to support those on the front lines helping communities adapt to climate change.
Learn more at wawanesa.com.

Equal Opportunity

Wawanesa is committed to diversity, equity, inclusion, and belonging (DEIB) and believes our strength lies in our diverse workforce, representative of the population.
We encourage all qualified candidates to apply, including visible minorities, women, Indigenous persons, persons with disabilities, members of the 2ELGBTQIA+ community, persons of diverse gender identities, and neurodiverse individuals, or anyone who can contribute to greater diversity of perspectives and ideas.
We want to ensure our recruitment process is accessible to all candidates. If you require accommodation during the recruitment process, please confidentially email jobs@wawanesa.com.
All applicants for employment with Wawanesa are subject to the Employee Personal Information Policy.