Representative - Commercial Insurance Sales

Western Financial Group; Winnipeg; On-site; CAD 60,000 - 90,000; Full time

Benefits offered by this job

14 Paid Wellness Days

3 weeks vacation

Company matching savings programs

100% employer paid group benefits

Job summary

Western Financial Group is seeking a Commercial Insurance Sales Representative in Winnipeg. You will sell our Commercial Insurance programs to independent businesses across Canada, building long-term client relationships.

The role combines a base salary with unlimited commissions and bonus payouts, with a path to growth through a high-performance team. You will benefit from a people-first culture and strong support as you drive results.

Qualifications

• FOI license an asset and may be required within 3 months.
• Post-secondary diploma or degree an asset.
• Proven relationship builder with strong negotiation, selling, and closing skills.
• Hunter mindset with entrepreneurial outlook to pursue new opportunities.

Responsibilities

• Generate new business opportunities both independently and with the team.
• Strategize and refine sales approach to target market prospects.
• Engage prospects via cold calls and build long-term client relationships.
• Navigate the sales process with effective information gathering and closing.

Skills

Relationship building

Negotiation

Closing techniques

Sales skills

Cold calling

CRM usage

Education

Post-secondary diploma or degree

Tools

CRM software

Job description

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 2,500 team members supporting over one million customers across 200+ locations across Canada.

Commercial 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
• Compensation: $40,000 salary + 40% commission on new business
• Requisition #: 83243

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 [e-mail] 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.