Region Field Trainer

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.

 Where You’ll Make an Impact:

The Regional Field Trainer is responsible for the delivery of learning activities focused on new hire training and other training activities and supports the development of our sales teams. Reporting to the Manager, Sales Enablement, the incumbent will be driving results through expert delivery, development and facilitation of sales specific learning programs. They will support the development of OSL’s US Sales teams and leaders to accelerate sales performance and effectiveness.

Execution Starts with You!

• Facilitate sales and sales training that will be executed through classroom, on-the-job training, train-the-trainer as well as synchronous and asynchronous e-learning strategies
• Keep sales force within boundaries of sales excellence in the metrics needed by their current program. (Sam’s, WMUS, WMUS ESP, Etc)
• Validate and comply with sales growth expectations and needs of the business in an ever changing—ever growing company with our corporate client partners. Assess needs of the business and have measured impacts to regional KPIs. (Subject to change with the needs of the business; such KPI lifts can be changed on a quarterly basis.)
• Implement and execute new employee onboarding, sales/operations training, product training, talent development and growth initiative programs to accelerate sales associate performance
• Build strong relationships and partner with Regional Director(s), District Managers and Team Leads to drive learning initiatives in-market
• Partner with a variety of outside vendors and corporate liaisons to build central growth strategies.
• Including but no limited to local client management, local level vendor partners, vendor partner trainers, and our internal learning enablement team.
• Have candid conversations with managers and associates to raise their awareness of development opportunities and connect them to resources
• Oversee and maintain training material and curriculum resources with upward feedback to Manager of Sales Enablement.
• Distribute training aids, such as instructional material, handouts, evaluation forms, etc.
• Create and maintain training schedules for existing employees and new hires
• Liaise with vendors/carrier partners as directed by OSL HQ to drive learning objectives
• Maintain alignment with OSL corporate budget
• Other projects and duties as assigned

What You Bring to The Table:

• Degree or Diploma in a business-related field; equivalent experience may be considered
• 3+ years of experience in a sales or training role in the retail industry
• Have the strong ability to motivate, inspire and build long lasting relationships within all levels of the organization
• Must be self-motivated and keen to build and develop your own career through constant learning
• Demonstrate credibility; knowledge of all learning platforms, product knowledge and training materials
• Strong understanding and execution of selling processes
• Be able to downwardly communicate sales process to a team of people and be able to measure impacts in both qualitative and quantitative terms.
• Strong knowledge of and confidence with MS Excel, Word, PowerPoint and webinar platforms
• Must have high level of organizational, time management and critical thinking skills
• Experience in facilitating small and large groups
• The successful candidate will be energetic, responsive, decisive and must possess a good knowledge of the wireless industry
• Strong communication and influencing skills (verbal, written, presentations)
• Strong relationship management skills to establish trust and credibility with associates, business leaders, and subject matter experts; getting results with and through others without formal authority• Travel (approx. 60-80%)

Internal candidates must meet the following criteria:

• 6 months in current position
• Meeting all performance expectations
• Discuss with their Manager prior to applying for the position.
• Sounds like a good fit? Well, let’s talk!

 So, What’s in it For You?

While the starting salary for this role typically begins at 50K your final offer will reflect your relevant skills, individual strengths and experience.

Let's Talk Perks

Beyond the numbers, we’re proud to offer a holistic package that includes bonus opportunities, room to grow, chances to be recognized, top-tier benefits, and perks that make coming to work something you can actually look forward to. We’re committed to supporting your success every step of the way.

Let’s chat about your Total Rewards:

• Generous time off: Start with 3 weeks of vacation, plus extra flex days to recharge.
• Comprehensive benefits package: Includes medical, dental, vision, health spending account, and Teladoc virtual care.
• Retirement support: Company-sponsored savings plan to help build your financial future.
• Fully Remote: Work where you’re most productive—no commute required.
• Top-tier tools: Best-in-class systems and equipment so you can do your best work.
• OSL Cares: Opportunities to give back through community and charity initiatives.
• WE at OSL: Supporting women’s empowerment and leadership.
• Career growth: Ongoing training, development, and programs to help you advance.
• Culture & Connection: Stay engaged with regular company-wide town halls, team-building events, etc.
• 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.
• Perks & Discounts: Enjoy savings on electronics, fitness memberships, and more through exclusive employee programs.
• Committed to Sustainability: We take environmental responsibility seriously by partnering with certified electronic recycling organizations to reduce our ecological footprint.

Recruitment Process 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 a virtual conversation with the hiring manager.
• Step 3: The final step is an in-person interview with the extended team members.

Ready to bring your talent to a team where your impact matters? Apply today — we can’t wait to meet you!

We thank all interested applicants; however, only qualified candidates will be contacted.  This position requires the successful completion of a criminal background check. OSL is committed to an inclusive workplace that does not discriminate against race, nationality, religion, age, marital status, physical or mental disability, sexual orientation, gender, or gender identity. We believe in diversity and encourage any qualified individual to apply.

 Disclaimer: 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.