Director, Training and Sales Enablement

Overview

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:

Reporting to the Senior VP Sales Enablement, we are recruiting a Director, Training and Sales Enablement. As a seasoned, successful sales driver, you will have experience running large scale sales teams, providing 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, 8000 strong, in a fast‑paced retail and direct sales environment.

Strategic Leadership:

• Set an enterprise-wide field training strategy, aligning all field training priorities with up-to-date, diverse delivery models, and capability development to strengthen OSL’s business and growth objectives.
• Translate support‑center strategies into effective replication in‑field sales execution.
• Demonstrates proven results in similar roles that show scale, impact and ROI models.

Field Sales Training Strategy & Execution:

• Build and oversee the execution of consistent field training programs to efficiently support frontline employees across North America for the entire employe lifecycle 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 complete framework to build and sustain outstanding coaching skills with strong organizational and interpersonal skills.
• Analyze performance data, skills gaps, and field feedback to identify training needs and improvement opportunities.
• Creating strong partnerships with Operations, Client Services, Sales, HR/Talent by tailoring 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.

To be successful and join our team:

• 10+ years of progressive experience in sales training, driving sales operations, performance enablement, and 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; Dashboarding and Power BI and comfort adopting learning and performance technologies.

Let's Talk Perks:

While the salary range for this role is $125k to $140k, your final compensation will reflect your years of experience and beyond the numbers, we’re proud to offer a holistic package that includes:

• 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?

Interview Steps:

• 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 SVP Sales Enablement & SVP HR/TA.
• Step 3: Final step is an in-person interview with the Chief Operating Officer.

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.