Representative- Cmrcl Sales
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.
Insurance Sales Representative
Carve your path to success by learning from industry sales experts who sell our unique Commercial Insurance programs to independent businesses across Canada. Our high-performance team will help you enhance your discipline and help refine the skills required to achieve your goals.
Western offers our Commercial Sales representatives an annual base salary plus unlimited commissions, including annual and monthly bonus payouts.
Here Is What a Typical Day Looks Like
Support the innate desire to generate new business opportunities both independently and working as a team Strategize and refine your sales approach by focusing on target market prospects Constantly adapt your cold-calling strategies to attract new customers, set personal quotas and monitor your performance using proven KPIs, Possess the confidence to interact with clients while obtaining relevant information through our sophisticated sales process Demonstrate superior active listening skills to understand prospects' needs through building long-term, trusting relationships and turn leads as sales opportunities Exhibit outstanding organizational skills to efficiently navigate our CRM program
The value you bring
FOI License an asset (will be required to obtain within 3 months) Post-Secondary diploma or degree an asset 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
Role Details
Hours: Full Time, Permanent (37.5 hours/week) Location: Office role in Winnipeg Current Vacancy: Pipeline role Compensation: $40,000 salary + 40% commission on new business Requisition #: 82968
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 Representative jobs in Winnipeg, Manitoba, Canada
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.
Similar Jobs
Representative- Cmrcl Sales
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.
Insurance Sales Representative
Carve your path to success by learning from industry sales experts who sell our unique Commercial Insurance programs to independent businesses across Canada. Our high-performance team will help you enhance your discipline and help refine the skills required to achieve your goals.
Western offers our Commercial Sales representatives an annual base salary plus unlimited commissions, including annual and monthly bonus payouts.
Here Is What a Typical Day Looks Like
Support the innate desire to generate new business opportunities both independently and working as a team Strategize and refine your sales approach by focusing on target market prospects Constantly adapt your cold-calling strategies to attract new customers, set personal quotas and monitor your performance using proven KPIs, Possess the confidence to interact with clients while obtaining relevant information through our sophisticated sales process Demonstrate superior active listening skills to understand prospects' needs through building long-term, trusting relationships and turn leads as sales opportunities Exhibit outstanding organizational skills to efficiently navigate our CRM program
The value you bring
FOI License an asset (will be required to obtain within 3 months) Post-Secondary diploma or degree an asset 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
Role Details
Hours: Full Time, Permanent (37.5 hours/week) Location: Office role in Winnipeg Current Vacancy: Pipeline role Compensation: $40,000 salary + 40% commission on new business Requisition #: 82968
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 Representative jobs in Winnipeg, Manitoba, Canada
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.