Commercial Sales Team Lead

Western Financial Group; Winnipeg; On-site; CAD 55,000 - 68,000; Full time

Benefits offered by this job

14 Paid Wellness Days

3 weeks’ vacation

100% employer paid group benefits

Discretionary quarterly performance bonus

Job summary

Western Financial Group is seeking a Team Lead – Commercial Sales in Winnipeg to guide and support a sales team. You will lead training efforts, drive a strong team culture, and contribute to operational accuracy in meeting sales goals.

The ideal candidate has leadership experience in commercial insurance and excels in client interactions. Join us as we prioritize people, purpose, and community impact.

Highlights include competitive salary and wellness benefits aimed at supporting employee growth.

Qualifications

• At least 2 years of Commercial insurance experience.
• Experience leading and coaching a sales team.
• Ability to work in a fast-paced environment.

Responsibilities

• Lead, coach, and inspire a team of Commercial Sales Representatives.
• Support sales reps in client meetings and presentations.
• Ensure accuracy in sales processes and client experiences.

Skills

Leadership skills

Commercial insurance experience

Attention to detail

Decision-making

Organizational skills

Results orientation

Strategic thinking

Education

Level 2 License

Job description

Overview

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.

Team Lead – Commercial Sales

We are seeking a Team Lead, Commercial Sales to guide, coach, and support a team of Commercial Sales Representatives. In this role, you will champion Western’s strategic goals, foster a positive team culture, and play a key part in developing sales talent throughout their first year. You will also support day‑to‑day sales activities, ensure operational accuracy, and contribute to planning and performance optimization.

Responsibilities

• Lead, coach, and inspire a high‑performing team of Commercial Sales Representatives from onboarding through ongoing development.
• Create a positive, collaborative team culture that aligns with Western’s mission and drives strong sales results.
• Support reps in client meetings, presentations, and closing opportunities to help them succeed and grow.
• Ensure accuracy in sales processes, data entry, and policy reviews to deliver a seamless client experience.
• Provide hands‑on coaching through shadowing and real‑time feedback to elevate sales performance.
• Monitor team metrics, identify productivity opportunities, and contribute to business planning and reporting.

The value you bring

• Level 2 License and at least 2 years of Commercial insurance experience.
• Strong leadership skills with the ability to coach, mentor, and motivate others.
• High attention to detail and strong decision‑making abilities.
• Ability to work in a fast‑paced environment with excellent organizational and prioritization skills.
• Strong results orientation and strategic thinking.
• Familiarity with sales processing, lead management, and routing.

Role Details

• Hours: Full Time, Permanent - Availability to work a total of 37.5 hours/week
• Location: In Office Role in Winnipeg
• Current Vacancy: Yes
• Compensation: $55,000 – $68,000
• Eligible for discretionary quarterly performance bonus
• Requisition #: 82909

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.

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.