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OSL Retail Services

Connects brands with shoppers through retail sales

Key Holder

Full-TimeDeadline 8/31/27
CA$30/hr+ Bonus
Mid
Toronto, ON, Canada
In Person
RetailRetail Store Management

About the job

Requirements
  • At least three years of retail or comparable service-led consumer care experience.
  • One to two years of responsibility for coaching, supervising or leading a team.
  • Intermediate knowledge of point-of-sale, inventory, scheduling and Microsoft Office systems.
  • Proven success delivering exceptional service alongside measurable targets.
  • Demonstrated ability to develop talent, address performance and coach toward a clear objective.
  • Strong judgment, reliable follow-through and calm decision-making under pressure.
  • Availability to work opening, closing, evening, weekend and holiday shifts as required.
  • The position requires following age-verification, privacy, marketing, health and safety, security, cash-handling and operating requirements.
Responsibilities
  • Open and close the location according to approved security, alarm and access procedures.
  • Complete assigned cash, safe, point-of-sale and end-of-day controls accurately.
  • Protect keys, access credentials, confidential information, inventory and company assets.
  • Escalate incidents promptly, document required details and coordinate an appropriate response.
  • Serve as the accountable leader on duty when the Store Manager is unavailable.
  • Set daily priorities, assign coverage and keep each team member actively engaged.
  • Lead huddles, reinforce approved messaging and communicate operational updates.
  • Observe performance, provide timely feedback and deliver practical coaching.
  • Support one-on-one development conversations, roleplay and follow-up actions.
  • Assist with onboarding, scheduling, training and talent development as directed.
  • Model every consumer experience, sales process and after-sales standard.
  • Ensure adult consumers receive a warm, personalized and compliant experience.
  • Resolve elevated concerns with empathy, commercial judgment and approved solutions.
  • Monitor service quality, conversion, loyalty, net promoter and related performance indicators.
  • Translate results into clear actions that improve team execution.
  • Monitor stock, confirm deliveries and maintain accurate inventory practices.
  • Support forecasting, ordering, returns and faulty-product processes.
  • Check merchandising, cleanliness and equipment throughout the day.
  • Confirm required safety inspections, training completion and policy compliance.
  • Help manage schedules, labour hours, supplies and controllable costs.
  • Maintain consistent execution of standard operating procedures and head-office direction.
Desired Qualifications
  • Experience as a key holder within a premium or highly regulated retail setting.
  • Working knowledge of inventory forecasting, loss prevention and store-level financial controls.
  • English fluency or professional proficiency, plus additional language capability where relevant to the market.

About the company

OSL runs customer-facing sales programs for North American retailers and consumer brands, placing representatives in client locations to explain products and guide purchase decisions. It recruits and manages retail teams for in-store staffing and merchandising, then runs neighborhood marketing and door-to-door sales for business and consumer customers. The company also supports clients with e-commerce platform work that connects online and physical retail. Brands contract OSL to design and operate these sales services on their behalf, rather than buying a consumer product sold under OSL's name. Established in 2012, OSL is headquartered in Mississauga, Ontario.

Company Size

5,001-10,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Mississauga, Canada

Founded

2012

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Simplify's Take

What believers are saying

  • Sales training is paid: OSL's October 2026 Collingwood posting lists in-store and online learning plus structured career-development programs.
  • Field applicants join a North American network: OSL says its marketers work across 2,000+ retail stores.
  • Management earns external recognition: OSL retained Best Managed Companies Platinum Club status in May 2026, according to its announcement.

What critics are saying

  • Portland field sales requires schedule flexibility: OSL's August 2026 ad includes evenings, some weekends and frequent regional travel.
  • The vacancy is prospective: Collingwood's October 2026 OSL ad forecasts hiring and lists hourly pay plus per-sale commissions.
  • Prospecting requires personal transport: OSL's August 2026 Ziply Fiber posting specifies a personal vehicle and door-to-door sales work.

What makes OSL Retail Services unique

  • OSL holds Walmart Canada's wireless mandate: it is the exclusive provider and manages 1,700-plus locations across North America.
  • Sales programs include education: OSL's Walmart Canada work combines product guidance, new carrier partnerships and teams for store openings.
  • Client data sits in one system: OSL says every program includes OneSource for tracking performance and return on investment.

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