Director of Sales and Field Training
About The Position
As a seasoned, successful sales driver, the Director of Sales and Field Training has experience running large scale sales teams, with inspiring leadership that develops high performing sales professionals and builds winning sales culture. They provide enterprise-level leadership for the strategy, design, and execution of sales training, coaching, and capability development programs for OSL’s field‑based team in a fast‑paced retail and direct sales environment. This role is instrumental in driving sales excellence, operational consistency and scalable performance across more than 8,000 frontline employees. Accountable for aligning training strategy with enterprise priorities and field execution realities, the Director architects innovative, scalable learning ecosystems that accelerate performance and enable business growth.
Requirements
- 10+ years of progressive experience in sales training, sales operations, performance enablement, or transformation roles, ideally within retail or field‑based environments (telecom experience an asset).
- Demonstrated success leading enterprise‑scale sales 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
- Build and oversee the execution of consistent field training programs to efficiently support frontline employees across North America including onboarding, sales training, and ongoing development.
- Identify and implement new approaches, tools, and technologies to enhance training effectiveness and speed‑to‑competency.
- Inspire and mentor field employees fostering a culture of sales excellence.
- Provide outstanding coaching skills with strong organizational and interpersonal skills.
- Own the sales training and coaching framework, including content direction, updates, and delivery standards.
- Define success metrics and measure training effectiveness through sales performance, productivity, and execution outcomes.
- Analyze performance data, skills gaps, and field feedback to identify training needs and improvement opportunities.
- Build strong partnerships with Operations, Client Services, Sales, HR, and Leadership ensuring training alignment and impact.
- Conduct field visits to validate execution, gather feedback, and ensure training strategies translate effectively in field.
- 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.
Benefits
- Generous time off: Start with 3 weeks of vacation.
- Comprehensive benefits package: Includes medical, dental, vision and a health spending account.
- Retirement support: Company-sponsored RRSP matching program to help build your financial future.
- Structured employee development programs designed to help you thrive.
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
