Representative- Commercial Sales

Job summary

Generate new commercial insurance business independently and as part of a team by targeting prospects, adapting cold-calling strategies, and converting leads into sales. Build trusting client relationships, gather relevant information through the sales process, and track performance using CRM tools and KPIs.

Job details

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 Current Vacancy: Pipeline role Compensation: $40,000 salary + 40% commission on new business Requisition #: 83348 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.

What you’ll do

Generate new commercial insurance business independently and as part of a team by targeting prospects, adapting cold-calling strategies, and converting leads into sales. Build trusting client relationships, gather relevant information through the sales process, and track performance using CRM tools and KPIs.

Requirements

A Financial and Insurance (FOI) license is an asset and must be obtained within three months; a post-secondary diploma or degree is also an asset. Candidates should demonstrate relationship-building, negotiation, selling and closing skills, along with resilience, teamwork, a positive attitude, and an entrepreneurial approach to finding new business.

Benefits

• Paid Wellness Days
• Vacation
• Company Matching Savings Programs
• Employer-Paid Group Benefits

Listed skills

• Cold Calling · Preferred
• Negotiation · Preferred
• Communication · Preferred
• Organization · Preferred
• Performance Monitoring · Preferred
• Teamwork · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• New Business Development
• Cold Calling
• Sales Strategy
• Prospecting
• Client Relationship Building
• Active Listening
• Negotiation
• Closing Sales
• Communication
• Organization
• CRM Navigation
• Performance Monitoring
• Teamwork
• Resilience
• Entrepreneurial Mindset

Job areas

• Sales
• Finance & Accounting

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