Retail Field Trainer

Overview

At OSL Retail Services, we believe people are the heart of everything we do, and it is an exciting time to be part of something special! Our momentum is growing, and is fueled by innovation, collaboration, and a shared entrepreneurial spirit that drives real results. Founded in 2012 in Mississauga, Ontario, OSL delivers customized sales solutions in retail, direct sales, and customer acquisition, all built on a foundation of integrity, respect, and passion. Our culture thrives on connection, purpose, and growth. If you’re looking for a place where your talents are valued, your ideas matter, and your career can grow, we’d love to meet you.

About the role:

We are seeking a Retail Field Trainer. Reporting Customer Experience Manager, our ideal candidate is responsible for executing and continuously improve training programs that support customer experience, operational excellence and associate performance across retail stores. Responsible for designing and delivering the training that enhances customer journeys, product knowledge and service quality. This role directly contributes to associate engagement, service excellence, and customer satisfaction.

Region: Vancouver, British Columbia

What you’re responsible for:

Training Program Execution & Delivery

• Deliver and support training programs across onboarding, new store openings, product launches and operational processes
• Facilitate in-person and virtual training sessions while supporting the rollout of standardized programs across multiple locations
• Ensure all training content is current, accurate and aligned with brand standards and business objectives

Customer Experience & Journey Enablement

• Support the development and execution of training programs that enhance the end-to-end customer experience (in-store, online, and post-sale)
• Reinforce best-in-class service behaviors and brand expectations through training and coaching
• Identify customer experience gaps and implement training solutions to improve NPS, engagement, and service performance

Content Development & Continuous Improvement

• Develop and maintain training materials, playbooks and tools to support field teams and learning initiatives
• Enhance training content through innovative learning methods, digital tools and scalable self-service solutions
• Continuously refine training programs based on feedback, performance metrics and evolving business needs

Cross-Functional Collaboration

• Partner with operations, marketing, product and field leadership teams to align training initiatives with business priorities
• Support coordination of training efforts across multiple stakeholders and initiatives
• Act as a liaison between field teams and corporate stakeholders to ensure alignment and consistency in execution

Innovation & Program Optimization

• Contribute to the evolution of training programs by identifying opportunities for innovation and improved delivery methods
• Support integration of new tools, technologies and methodologies that enhance training effectiveness
• Promote a culture of continuous learning and development across the organization

Performance Tracking & Insights

• Track training effectiveness using key metrics (e.g., engagement, knowledge retention, performance outcomes)
• Analyze training results to identify trends, gaps, and opportunities for improvement
• Provide insights and recommendations to improve training impact and business outcomes

Project & Program Support

• Assist with planning, coordination, and rollout of training programs across regions
• Contribute to communication, adoption, and implementation of new processes and initiatives

Travel Requirements:

• 10% travel
• Estimated 1 trip quarterly to Calgary AB

Job Requirements:

• 4+ years of experience in training, learning & development, retail operations, or customer experience roles
• Bachelor’s degree in business, Education, HR, or a related field preferred
• Strong facilitation and presentation skills, with the ability to engage diverse audiences
• Experience developing and delivering training content in fast-paced, customer-facing environments
• Strong understanding of customer experience principles and retail service delivery
• Ability to analyze performance data and translate insights into actionable improvements
• Strong communication, organization, and stakeholder collaboration skills
• Ability to manage multiple priorities in a dynamic, high-growth environment
• Proficiency in Microsoft Office (PowerPoint, Excel, Word); experience with LMS platforms is an asset

Let's Talk Perks:

While the starting salary for this role typically begins at $60k - $85k, your final offer will reflect your relevant skills, individual strengths and experience. Beyond the numbers, we’re proud to offer a holistic package that includes bonus opportunities, room to grow, chances to be recognized, top-tier benefits, and perks that make coming to work something you can look forward to. We’re committed to supporting your success every step of the way.

• Generous time off: Start with 3 weeks of vacation, plus extra flex days to recharge
• Comprehensive benefits package: Includes medical, dental, vision, health spending account, and Teladoc virtual care
• Retirement support: Company-sponsored savings plan to help build your financial future
• Top-tier tools: Best-in-class systems and equipment so you can do your best work
• OSL Cares: Opportunities to give back through community and charity initiatives
• Career growth: Ongoing training, development, and programs to help you advance
• Award-winning culture: Proud to be one of Canada’s Best Managed Companies for 8 years running — now a Platinum Club member.
• Invested in you: Structured employee development programs designed to help you thrive.
• Perks & Discounts: Enjoy savings on electronics, fitness memberships, and more through exclusive employee programs.

The Interview Process:

• Step 1: If your profile is a match, we will invite you for a first conversation with the recruiter.
• Step 2: The next step is an in-person interview with the hiring Manager.
• Step 3: The next step is an in-person interview with the hiring Manager and Director.

If this sounds like you and you are excited to be a member of our team, please apply now.

Disclaimer: As part of our recruitment process, we utilize artificial intelligence (AI)-based tools to assist with certain stages, including initial resume screening and skills-matching assessments. These tools are designed to help our hiring team identify candidates whose experience and qualifications align closely with the requirements of the role. Please note that all final hiring decisions are made by our recruitment team. The preceding job description has been designed to indicate the general nature and level of work performed by employees within this job. It is not designed to contain or be interpreted as a comprehensive inventory of all duties, responsibilities and qualifications required of employees assigned to this job. In compliance with Ontario’s Bill 190, we confirm that this posting represents a current existing vacancy within our organization.