Manager Direct Sales Jobs in Ontario (NOW HIRING)

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.

As a seasoned, successful sales driver, the Director of Sales 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.

• 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.

• Build and oversee the execution of consistent field 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.
• Inspire and mentor field employees fostering a culture of sales excellence.
• Define success metrics and measure training effectiveness through sales performance, productivity, and execution outcomes.

• 10+ years experinece in sales operations and training, performance enablement ideally within retail or field based environments, telecom experinece 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, 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?

• 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 hiring manager.
• Step 3: In-person panel presentation with the VP Operations and extended Senior Leaders.
• Step 4: Final step is an in-person interview with the Chief Operating Officer.

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