Sales Director

OSL Retail Services; Mississauga; On-site; CAD 125,000 - 140,000; Full time

Benefits offered by this job

3 weeks vacation

Medical, dental, vision

RRSP matching

Best Managed Company Platinum Club

Structured employee development

Job summary

OSL Retail Services in Mississauga, Ontario, seeks a Director of Sales and Field Training to lead enterprise-level training strategy and field execution for over 8,000 frontline employees across North America. You will shape training programs, guide content development, and drive performance enablement in a fast-paced retail environment.

Ideal candidates bring 10+ years in sales training and leadership, with a track record of scaling training functions, coaching excellence, and strong analytical

Qualifications

• 10+ years of progressive experience in sales training, sales operations, or performance enablement within retail or field-based environments.
• Demonstrated success leading enterprise-scale sales training or capability development functions.
• Exceptional people development, coaching, and performance enablement skills.
• Strong communication and influencing skills with dispersed field teams.

Responsibilities

• Set the enterprise field training strategy, aligning priorities, delivery models, and capability development to business objectives.
• Build and oversee consistent field sales training programs across North America.
• Identify and implement new approaches, tools, and technologies to enhance training effectiveness.
• Own the sales training and coaching framework, including content direction, updates, and delivery standards.

Skills

Sales leadership

Coaching

Performance enablement

Communication

Strategic planning

Analytical thinking

Tools

MS Office

Job description

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.

About the opportunity - Sales Director and Field Training, Mississauga Ontario. (CANADA)

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.

Role Responsibilities:

Strategic Leadership:

• 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.

Field Sales Training Strategy & Execution:

• Build and oversee the execution of consistent field sales training programs to efficiently support frontline employees across North America.
• Identify and implement new approaches, tools, and technologies to enhance training effectiveness and speed-to-competency.
• Own the sales training and coaching framework, including content direction, updates, and delivery standards.

To be successful and join our team:

• 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.

The salary range for this role is $125k to $140k

• 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.
• Award-winning culture: Proud to be one of Canada's Best Managed Companies for 8 years running - now a Platinum Club member.
• Invested in you: Structured employee development programs designed to help you thrive.

We're committed to supporting your success every step of the way. What are the next steps?

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