Director of Field Sales Training
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Key skills for this role
About the Role
OSL Retail Services seeks a Director of Field Sales Training to lead enterprise-level training strategy and execution for a field-based workforce of 7,000+ frontline employees.
Key Skills for This Role
Responsibilities
- Set the enterprise field training strategy, aligning training priorities, delivery models, and capability development to OSL’s business and growth objectives.
- Build and oversee the execution of field training programs to efficiently support frontline employees across North America.
- Own the sales training and coaching framework, including content direction, updates, and delivery standards.
- 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.
- Build strong partnerships with Operations, Client Services, Sales, HR, and Leadership to ensure training alignment and impact.
- Lead the Training function’s structure, priorities, and operating model to deliver high quality, consistent outcomes.
- Manage the training budget responsibly, balancing investment with impact and return.
Requirements
- 10+ years of progressive experience in training, sales operations, performance enablement, or transformation roles, ideally within retail or field based environments
- 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
Full Job Posting
Overview
- At OSL Retail Services, we believe people are the heart of everything we do.
- We are currently seeking a Director of Field Sales Training.
- As Director of Field Sales 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.
- Location: Mississauga.
Key Responsibilities
- 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.
Performance Measurement & Effectiveness
- 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.
Cross Functional Alignment & Field Partnership
- 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.
Operational Excellence & Resource Management
- 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.
Field Team Development
- 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.
To be successful and join our team
- 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.
What we offer
- A competitive base salary CAD 125K CAD 140K plus bonus.
- Vacation plus additional flex days.
- Comprehensive benefits.
- RRSP Matching Program.
- Training and development opportunities to grow your career with one of Canada’s Best Managed Companies.
- A supportive workplace culture and work environment.
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