Retail Support Executive - Winnipeg

Retail Support Executive (Territory-Based)

Location: Winnipeg, MB

About the Role:

We are seeking a high-performing and driven Retail Support Executive (Territory-Based) to bridge the gap between frontline sales execution and Team Leads. This role is ideal for an experienced sales professional who consistently exceeds targets, demonstrates strong product expertise, and is ready to take on expanded responsibilities including peer support, field guidance, and territory optimization.

As a key contributor in the field, you will not only drive sales and elevate the customer experience but also act as a trusted in-store partner, supporting the execution and growth of a smoke-free product portfolio across multiple retail locations, conducting product demonstrations, and ensuring territories are optimized for maximum engagement and sales performance.

Compensation & Schedule

• One year contract starting January 2027
• 28-35 hours per week (weekdays and weekends)
• 4-5 days per week (7-hour shifts, including paid travel time), between 12 p.m. and 9 p.m.
• Hourly rate: Starting at $27/hour + performance incentives and a bonus upon successful completion of the contract
• Paid training

What You’ll Do

Sales Performance & Execution

· Consistently achieve and exceed individual sales targets and KPIs.

· Deliver exceptional customer engagement through confident product education and hands-on demonstrations across multiple product categories (e.g., IQOS devices, VEEV products, combustibles, promotions).

· Drive customer acquisition, registration, and retention through effective selling techniques.

· Identify opportunities to increase sales performance and in-store conversion within assigned locations.

Territory Support & In-Store Execution

· Manage and optimize a designated territory, ensuring strong coverage and consistent brand execution across retail locations (1–3 locations per shift; 3–4 hours per location).

· Build and maintain strong relationships with retail staff, store teams, and key stakeholders.

· Provide insights on store performance, customer trends, and opportunities for growth.

· Ensure retail environments are prepared and positioned to convert customer interest into confident product adoption.

Coaching & Peer Support

· Act as a mentor and resource for Sales Brand Ambassadors, supporting onboarding and ongoing development.

· Share best practices, sales techniques, and product knowledge with peers.

· Provide informal, on-the-ground coaching to support team success.

Operational Excellence & Compliance

· Ensure accurate and timely reporting of sales activities, customer registrations, and field insights.

· Support execution of campaigns, product launches, and field initiatives.

· Identify and troubleshoot in-store challenges with a proactive, solution-oriented approach.

· Handle sensitive customer information responsibly and in compliance with program and regulatory requirements.

What You Bring

· 2–3+ years of experience in retail, field sales, or customer-facing roles.

· Proven track record of meeting or exceeding sales targets.

· Strong communication, interpersonal, and product knowledge skills with a customer-first mindset.

· Demonstrated ability to influence, support, and guide peers (informal leadership experience is an asset).

· Highly organized, proactive, and able to work independently in a fast-paced, territory-based environment.

· Tech-savvy with experience using mobile reporting tools.

· Flexible, adaptable, and able to navigate varying retail environments and customer dynamics.

Additional Requirements

· Valid driver’s license and access to a reliable vehicle.

· Flexibility to work evenings and weekends as needed.

· Ability to travel within the assigned territory.

· Comfortable with a physically active role (standing, engaging customers, transporting materials up to 50 lbs).

Perks

· Performance-Based Incentives: Competitive bonus structure aligned with program objectives and performance outcomes.

· Professional Development: Opportunity to build expertise across a multi-category product portfolio.

· Autonomy & Ownership: Manage your territory and contribute directly to in-store success.

Job Status: Open Position

About Brand Momentum

Brand Momentum is a nationally integrated leader in Sales, Marketing, and Retail, with headquarters in Toronto. We foster authentic and enduring human connections across the nation. As a three-time winner of Canada's Top 100 Best Workplaces® and one of Canada's fastest-growing companies, we take pride in our commitment to 'Goodness,' a core value that permeates everything we do.

Our Commitment

· Enduring Success: We are not just about achieving success; we're about sustaining it. As a market leader in quality and innovation, we foster a fun culture where both employee and client aspirations can be realized.

· Delivering on Promises: We are passionate about delivering on our promises to both clients and our people. Our innovative approach ensures we consistently provide exceptional value and flexibility, always striving to exceed expectations.

· Core Values: Our commitment to integrity, respect, empowerment, and fun is woven into the fabric of our company. We believe in fostering a responsible and flexible work environment that allows our team members to thrive.

· Sustainability: We prioritize sustainable suppliers and work with vendors and clients to offset the environmental impact of our programs, contributing to a greener future.

· Diversity and Inclusion: We are dedicated to fostering a culturally diverse workplace. We value diverse perspectives and are committed to building a team that celebrates individual backgrounds, experiences, and talents. We believe in the power of diversity to drive stronger, more innovative outcomes.

We are committed to providing accommodations for persons with disabilities. If you require an accommodation, we will work with you to meet your needs, to the extent required by law.

Job Status: Open Position