Director of Field Sales Training
About The Position
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 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. 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.
Requirements
- 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.
Nice To Haves
- telecom experience an asset
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.
- 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.
Benefits
- A competitive base salary $125K-$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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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
