Retail Field Trainer

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.

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.

• 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

• 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

• 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

• 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

• 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

• 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

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

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

• 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