Representative - Employee Benefits Sales

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.

Employee Benefit Sales Representative - Winnipeg

Carve your path to success by learning from industry sales experts who sell our unique Employee Benefit Insurance programs to independent businesses across Canada.

Our high-performance team will help you enhance your discipline and help you refine the skills required to achieve your goals.

Western offers our Employee Benefits Sales representatives an Annual base Salary plus unlimited commissions, including Annual and monthly bonus payouts. Our Empress location also includes an Onsite Gym and Parking.

The Expectation

• 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 with prospects to qualify leads as sales opportunities
• Exhibit outstanding organizational skills to efficiently navigate our CRM program
  
  

What You Bring

• LLQP License an asset
• 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 + 30% commission on new business
• Requisition #: 82941
  
  

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.