Commercial Insurances Sales Representative
Top Benefits
About the role
Proudly Canadian. Driven by Purpose. Rooted in Care.
Join a national team where people, purpose, and community come first. Western Financial Group was named a 2025 Top Insurance Employer by Insurance Business Canada and is home to more than 2,300 team members supporting over one million customers across 200+ locations across Canada.
Representative - Commercial Sales
Our Digital Sales Team is Western’s fastest growing sales channel, which uses internal leads to drive organic growth. In this role you will be provided warm leads from our website and earn commission on every sale.
Here is what a typical day looks like
- Conduct sales calls for new online leads provided to you by the Business
- Up-sell & cross-sell when talking to customers on all our insurance products
- Best match client needs to insurance company offerings
The value you bring
- General Insurance License required
- At leat 1 year selling insurance, commercial lines products preferred
- Proven relationship builder with strong negotiation, selling, and closing techniques
- A resilient team player who is driven to achieve results with a positive attitude
- A hunter mindset with an entrepreneurial mentality for proactively seeking and closing new business opportunities in the market
If you are looking for a role that feeds into your passion for sales and getting recognized for exceeding sales targets, this role offers you the opportunity to directly impact our customer experience. Your creative problem solving to find solutions for clients and ability to communicate them professionally combined with your persistence and ability to adapt to changing customer needs will accelerate your success.
Role Details
- Hours: Full Time, Permanent (37.5 hours/week)
- Location: Office Role in Winnipeg
- Current Vacancy: Yes
- Compensation: $40,000 salary + 40% commission on new business
- Requisition #: 82791
Why Western?
Western’s people-first culture, grounded in our guiding principles of Truthfulness, Fairness, Value, and Loyalty, is recognized across Canada and strengthened by our commitment to wellness, flexibility, and meaningful community impact.
Highlights include:
- 14 Paid Wellness Days, 3 weeks’ vacation, company matching savings programs, and 100% employer paid group benefits for eligible employees
- Over 1,500 volunteer hours supporting 160+ charities in 2024–2025 through the Western Financial Group Communities Foundation.
Our Commitment to Inclusion: At Western, we strive to create an accessible, equitable, and inclusive workplace where everyone feels valued and can thrive. As an equal opportunity employer, we encourage applicants of all backgrounds to apply, even if your experience doesn’t perfectly match every qualification. If you need assistance or an accommodation during the hiring process, please contact talent.acquisition@westernfg.ca or visit our Careers page.
Our Human First Hiring Approach: We do not use artificial intelligence to screen, assess, or select applicants. All applications are personally reviewed by Western’s Talent Acquisition Consultants. As part of our hiring process, we use standardized, scientifically validated skills assessments (nonAI), and all results are reviewed by our hiring team.
Ready to Apply?
If making a meaningful impact in your community and growing your career in a supportive, purpose-driven environment excite you, we’d love to hear from you.
Not the right fit? Search for Commercial Insurances Sales Representative jobs in Winnipeg, MB
About Western Financial Group
Western Financial Group is a diversified insurance services company that is focused on creating security and has provided over one million Canadians the right protection for more than 100 years. Headquartered in High River, Alberta, Western provides personal and business insurance through 220 locations, its affiliates and a variety of connected channels, with an engaged team of approximately 2,100 people.
Day in and day out, the interactions of our people are rooted in four guiding principles: Truthfulness, Fairness, Value and Loyalty. For customers, that means honesty and accountability from your Western insurance experts; trust and loyalty; hard-earned knowledge of our business; and longstanding relationships with enduring value.
Western Financial Group is a subsidiary of Trimont Financial, a wholly-owned subsidiary of The Wawanesa Mutual Insurance Company.
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Commercial Insurances Sales Representative
Top Benefits
About the role
Proudly Canadian. Driven by Purpose. Rooted in Care.
Join a national team where people, purpose, and community come first. Western Financial Group was named a 2025 Top Insurance Employer by Insurance Business Canada and is home to more than 2,300 team members supporting over one million customers across 200+ locations across Canada.
Representative - Commercial Sales
Our Digital Sales Team is Western’s fastest growing sales channel, which uses internal leads to drive organic growth. In this role you will be provided warm leads from our website and earn commission on every sale.
Here is what a typical day looks like
- Conduct sales calls for new online leads provided to you by the Business
- Up-sell & cross-sell when talking to customers on all our insurance products
- Best match client needs to insurance company offerings
The value you bring
- General Insurance License required
- At leat 1 year selling insurance, commercial lines products preferred
- Proven relationship builder with strong negotiation, selling, and closing techniques
- A resilient team player who is driven to achieve results with a positive attitude
- A hunter mindset with an entrepreneurial mentality for proactively seeking and closing new business opportunities in the market
If you are looking for a role that feeds into your passion for sales and getting recognized for exceeding sales targets, this role offers you the opportunity to directly impact our customer experience. Your creative problem solving to find solutions for clients and ability to communicate them professionally combined with your persistence and ability to adapt to changing customer needs will accelerate your success.
Role Details
- Hours: Full Time, Permanent (37.5 hours/week)
- Location: Office Role in Winnipeg
- Current Vacancy: Yes
- Compensation: $40,000 salary + 40% commission on new business
- Requisition #: 82791
Why Western?
Western’s people-first culture, grounded in our guiding principles of Truthfulness, Fairness, Value, and Loyalty, is recognized across Canada and strengthened by our commitment to wellness, flexibility, and meaningful community impact.
Highlights include:
- 14 Paid Wellness Days, 3 weeks’ vacation, company matching savings programs, and 100% employer paid group benefits for eligible employees
- Over 1,500 volunteer hours supporting 160+ charities in 2024–2025 through the Western Financial Group Communities Foundation.
Our Commitment to Inclusion: At Western, we strive to create an accessible, equitable, and inclusive workplace where everyone feels valued and can thrive. As an equal opportunity employer, we encourage applicants of all backgrounds to apply, even if your experience doesn’t perfectly match every qualification. If you need assistance or an accommodation during the hiring process, please contact talent.acquisition@westernfg.ca or visit our Careers page.
Our Human First Hiring Approach: We do not use artificial intelligence to screen, assess, or select applicants. All applications are personally reviewed by Western’s Talent Acquisition Consultants. As part of our hiring process, we use standardized, scientifically validated skills assessments (nonAI), and all results are reviewed by our hiring team.
Ready to Apply?
If making a meaningful impact in your community and growing your career in a supportive, purpose-driven environment excite you, we’d love to hear from you.
Not the right fit? Search for Commercial Insurances Sales Representative jobs in Winnipeg, MB
About Western Financial Group
Western Financial Group is a diversified insurance services company that is focused on creating security and has provided over one million Canadians the right protection for more than 100 years. Headquartered in High River, Alberta, Western provides personal and business insurance through 220 locations, its affiliates and a variety of connected channels, with an engaged team of approximately 2,100 people.
Day in and day out, the interactions of our people are rooted in four guiding principles: Truthfulness, Fairness, Value and Loyalty. For customers, that means honesty and accountability from your Western insurance experts; trust and loyalty; hard-earned knowledge of our business; and longstanding relationships with enduring value.
Western Financial Group is a subsidiary of Trimont Financial, a wholly-owned subsidiary of The Wawanesa Mutual Insurance Company.