Date: Jun 19, 2026
Location: Hybrid - Canada, CA
Company: Wawanesa Insurance
Job ID: 10121
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; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Lethbridge, AB; Toronto (North York), ON; Kitchener, ON; Ottawa.
Working Business Language : English. This role is considered a head-office role and will be required to communicate with internal and external stakeholders across Canada where the primary business language for this role is English. As such, the successful candidate must be fully proficient in 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: $120,000 - $145,000. 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 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 Manufacturing & Wholesale 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 VP, Commercial Lines, 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.
Job Responsibilities
Support the development of underwriting strategies, standards, tools, and pricing approaches for the mid-market segment, ensuring alignment with risk exposure, competitive benchmarks, and emerging trends to drive profitable growth and operational excellence
Act as a technical expert for the segment, supporting large account underwriting, file and portfolio reviews, and large loss analysis, while providing coaching and technical leadership to underwriters to strengthen underwriting quality and pricing adequacy
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
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 VP in monitoring and reporting on key portfolio performance metrics for the specific segment, hit ratio, loss ratio, growth, retention, mix, and broker performance, while identifying opportunities for growth, diversification and loss ratio improvement
Embed Wawanesa’s purpose and values into all aspects of leadership, building trust with members, enabling success for brokers, and creating value for communities
Promote inclusion, integrity, and fairness in how business is conducted, decisions are made, and teams are developed
Qualifications
Minimum 10 years of experience in commercial insurance, with deep expertise in mid-market underwriting in the specific segment
Bachelor’s degree in Business, Insurance, Risk Management, or a related field, along with a CIP or FCIP designation; an MBA or CRM designation is considered a strong asset
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
Experience underwriting mid-market commercial risks, with exposure to Manufacturing and Wholesale segments strongly preferred
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 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
[email protected] .
All Wawanesa job applicants are subject to Wawanesa's Privacy Policy .
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.
