Representative - Employee Benefits Sales

Western Financial Group; St. James Industrial; On-site; CAD 47,000 - 57,000; Full time

Benefits offered by this job

Onsite gym

Parking

Wellness days

Vacation days

Employer paid group benefits

Job summary

Western Financial Group is seeking an Employee Benefits Sales Representative for Winnipeg. This full‑time role combines building client relationships with proactive prospecting to drive new business across Canada.

Base salary is complemented by a generous commission structure, with an onsite gym and parking at the Winnipeg office. You will learn from sales experts and contribute to a high‑performance team focused on achieving personal quotas and KPIs through a proven process.

Qualifications

• Proven relationship builder with strong negotiation, selling and closing techniques.
• Hunter mindset with entrepreneurial drive to proactively seek and close new business opportunities.
• Ability to work in a target-driven sales environment with clear KPIs.

Responsibilities

• Support generation of new business opportunities both independently and in teams.
• Strategize and refine sales approach for target market prospects.
• Interact with clients through our sales process and qualify leads to convert to opportunities.
• Maintain organized CRM records and track performance against quotas.

Skills

Relationship building

Negotiation

Closing deals

Prospecting

Education

Post‑secondary diploma or degree

LLQP License (asset)

Tools

CRM software

Job description

Career Opportunities: Representative - Employee Benefits Sales (83349)

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 representativesan Annual base Salary plusunlimitedcommissions, 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
• Hours: Full Time, Permanent (37.5 hours/week)
• Location: Office role in Winnipeg
• 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

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.