VP, Commercial Lines, Small Business
Wawanesa Insurance
Date: 17 hours ago
City: Winnipeg, Manitoba
Contract type: Full time
Job ID: 9307
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: $220,000- $270,000. Candidates with salary expectations outside of the range are still encouraged to apply.
About Us
At Wawanesa, we’re proud to offer a hybrid work environment that offers flexibility to our employees in balancing in-office (3 days 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, ON; Kitchener, ON; Thunder Bay, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth; NS.
The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,600 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. To learn more visit 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 Vice President, Commercial Insurance – Small Business is responsible for leading the strategic development, growth, and profitability of Wawanesa’s national small commercial insurance portfolio defined as policies with under $20K in coverage value. This executive role oversees delivering on the profitable growth of small business including the underwriting strategy, risk selection, pricing, broker relations, and operational execution, ensuring that we deliver solutions that meet the needs of small business owners across Canada.
Reporting to the SVP & Chief Commercial Lines Officer, this leader plays a key role in advancing Wawanesa’s cooperative purpose. We are here to look after one another and instills our values of Service, Openness, Fairness, Collaboration, and Community through every touchpoint with members, employees, brokers, and partners.
Job Responsibilities
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.
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: $220,000- $270,000. Candidates with salary expectations outside of the range are still encouraged to apply.
About Us
At Wawanesa, we’re proud to offer a hybrid work environment that offers flexibility to our employees in balancing in-office (3 days 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, ON; Kitchener, ON; Thunder Bay, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth; NS.
The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,600 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. To learn more visit 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 Vice President, Commercial Insurance – Small Business is responsible for leading the strategic development, growth, and profitability of Wawanesa’s national small commercial insurance portfolio defined as policies with under $20K in coverage value. This executive role oversees delivering on the profitable growth of small business including the underwriting strategy, risk selection, pricing, broker relations, and operational execution, ensuring that we deliver solutions that meet the needs of small business owners across Canada.
Reporting to the SVP & Chief Commercial Lines Officer, this leader plays a key role in advancing Wawanesa’s cooperative purpose. We are here to look after one another and instills our values of Service, Openness, Fairness, Collaboration, and Community through every touchpoint with members, employees, brokers, and partners.
Job Responsibilities
- Develop and execute a national strategy for small business commercial insurance that delivers profitable growth, superior member experience, and operational efficiency.
- Oversee underwriting and portfolio management for small business policies, ensuring alignment with Wawanesa’s appetite, regulatory requirements, and risk frameworks.
- Collaborate with actuarial and pricing teams to create rating models and segmentation strategies that reflect small business market trends, competitive positioning, and member needs.
- Lead product innovation and modernization efforts for small commercial offerings, including digital enablement and broker channel enhancements.
- Provide executive oversight for operational execution, ensuring high-quality, consistent underwriting practices across all regions.
- Build and maintain strong relationships with broker partners, ensuring their needs are understood and supported through clear communication, responsive service, and aligned growth strategies.
- Monitor portfolio performance and trends, leveraging analytics to guide product refinement, underwriting discipline, and process improvements.
- Champion a collaborative approach with Claims, Risk, Legal, and Compliance functions to support underwriting integrity, appropriate risk-taking, and regulatory compliance.
- Inspire and lead a high-performing team across underwriting, product, and support functions, with a strong emphasis on coaching, development, and inclusion.
- Foster a culture that reflects Wawanesa’s values—placing member protection, trust, and fairness at the center of every decision.
- Represent Wawanesa in external industry forums and regulatory discussions as needed, advocating for the needs of small business members and mutual insurers.
- Bachelor’s degree in business, insurance, risk management, or a related field; MBA, CIP, or FCIP designation is a strong asset.
- Minimum 10 years of experience in Commercial Insurance, with a focus on Small Business or SME portfolios; at least 5 years in a senior leadership role.
- Proven track record of profitable growth, underwriting excellence, and strategic leadership in the small commercial market.
- Deep understanding of the Canadian P&C regulatory environment and competitive insurance landscape for small businesses.
- Strong collaboration and relationship-building skills, especially in working with brokers, partners, and internal teams.
- Demonstrated ability to lead transformational change, digital innovation, and cross-functional alignment.
- Exceptional business acumen, communication skills, and strategic thinking capabilities.
- Deep commitment to Wawanesa’s purpose and values, with a passion for supporting communities, protecting small businesses, and leading with integrity.
- Willingness to travel across regions as required.
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.
See more jobs in Winnipeg, MB