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.