Director of Field Training

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 currently seeking a Director of Field Training. As Director of Field Training, you will provide enterprise‑level leadership for the strategy, design, and execution of training and capability development programs for OSL’s field‑based workforce in a fast‑paced retail and direct sales environment. This role plays a pivotal part in enabling sales excellence, operational consistency, and scalable performance across 7,000+ frontline employees.

Operating at a director’s level, you are accountable for aligning training strategy to enterprise priorities and field execution realities. You will architect scalable learning models, leverage technology and data to improve effectiveness, and ensure training drives measurable improvements in sales productivity, execution quality, and employee capability.

• Set the enterprise field training strategy, aligning training priorities, delivery models, and capability development to OSL’s business and growth objectives.
• Translate support‑center strategies into effective, in‑field execution through structured learning, coaching, and reinforcement models.
• Identify future capability needs and design training approaches that support scale, innovation, and evolving field requirements.
• Partner with executive leadership to ensure field training is positioned as a strategic performance lever.

• Build and oversee the execution of field training programs to efficiently support frontline employees across North America.
• Own the design, governance, and continuous evolution of training delivery models, including onboarding, sales training, and ongoing development.
• Identify and implement new approaches, tools, and technologies to enhance training effectiveness and speed‑to‑competency.
• Ensure training programs are scalable, consistent, and adaptable across clients, regions, and field environments.

• Own the sales training and coaching framework, including content direction, updates, and delivery standards.
• Ensure coaching models reinforce desired behaviors, performance standards, and execution discipline.
• Align learning content with real‑world field execution, client expectations, and operational realities.

• Analyze performance data, skill gaps, and field feedback to identify training needs and improvement opportunities.
• Define success metrics and measure training effectiveness through sales performance, productivity, and execution outcomes.
• Continuously refine training strategies based on data, field input, and business results.

• Build strong partnerships with Operations, Client Services, Sales, HR, and Leadership to ensure training alignment and impact.
• Conduct periodic field visits to validate execution, gather feedback, and ensure training strategies translate effectively on the ground.
• Serve as a senior advisor on field capability and performance improvement initiatives.

• Lead the Training function’s structure, priorities, and operating model to deliver high‑quality, consistent outcomes.
• Oversee training content development requests and team capacity to ensure prioritization and execution discipline.
• Manage the training budget responsibly, balancing investment with impact and return.
• Drive continuous improvement across training processes, tools, and governance.

• Ability to manage changing priorities and keep the team motivated.
• Inspire and mentor field employees fostering a culture of sales excellence.
• Outstanding coaching skills combined with strong organizational and interpersonal skills.

• 10+ years of progressive experience in training, sales operations, performance enablement, or transformation roles, ideally within retail or field‑based environments (telecom experience an asset).
• Demonstrated success leading enterprise‑scale training or capability development functions.
• Exceptional people development, coaching, and performance enablement skills.
• Strong ability to operate in a fast‑paced, highly changeable environment with a practical, execution‑focused mindset.
• Excellent communication and influencing skills with experience engaging diverse, geographically dispersed field teams.
• Strong analytical and problem‑solving skills, with the ability to translate insight into action.
• Proficiency in MS Office; comfort adopting learning and performance technologies.

• 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: Final step is an in-person presentation with the VP Operations and extended team members.

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

We thank all interested applicants; however, only qualified candidates will be contacted.  This position requires successful completion of a criminal background check.

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.