Fleet Manager

Overview

Reporting to the Logistics & Donation Centre Manager, the Fleet Manager is responsible for overseeing the transportation and fleet operations that support the movement of goods between the Donation Centre, WINS retail stores, programs, and community partners. This role ensures safe, timely, efficient, and cost-effective transportation services through effective route planning, vehicle utilization, and driver coordination.

This position oversees transportation operations for a fleet of five trucks and provides leadership to a team of approximately 20 employees within a single 30,000-square-foot Distribution Centre.

The Fleet Manager is accountable for fleet maintenance, regulatory compliance, driver safety, and daily transportation operations. This role provides leadership and support to drivers and logistics staff while ensuring vehicles are properly maintained and transportation services operate efficiently and reliably. The Fleet Manager works collaboratively with warehouse and retail teams to support operational needs and maintain effective service delivery across the organization.

The Fleet Manager is responsible for optimizing fleet utilization, coordinating transportation schedules, monitoring key performance indicators, and ensuring compliance with all applicable safety and transportation regulations. This is a hands‑on operational leadership role focused on supporting a single‑site distribution operation and its transportation requirements.

• Plan and oversee daily transportation routes and fleet utilization to support operational requirements and service delivery.
• Coordinate transportation schedules and pickup/delivery requirements, including customer pickups, retail stores, warehouse teams, and community partners.
• Ensure safe, timely, and efficient transportation operations, including vehicle loading coordination and delivery execution.
• Oversee fleet maintenance schedules, vehicle inspections, and transportation practices to ensure safety, compliance, efficiency, and service reliability.
• Monitor transportation performance and identify opportunities to improve operational efficiency, routing, and service delivery.

• Ensure all transportation‑related health and safety policies and procedures are implemented and consistently followed.
• Monitor compliance with required personal protective equipment (PPE), safe driving practices, and workplace safety standards.
• Promote a strong transportation safety culture through training, incident prevention, compliance monitoring, and leadership.
• Report and respond to safety concerns, incidents, and operational hazards in a timely manner.

• Oversee preventative, routine, and emergency maintenance and repairs of WINS’ vehicle fleet
• Coordinate vehicle servicing, inspections, repairs, and maintenance schedules with internal departments and external service providers.
• Ensure fleet vehicles and transportation equipment are maintained in safe working conditions and operated in accordance with safety standards and manufacturer guidelines.
• Maintain accurate fleet records including vehicle inspections, maintenance history, repairs, licensing, and service schedules to support compliance and minimize downtime.
• Monitor vehicle condition and proactively identify maintenance needs to reduce operational disruptions and extend fleet life.
• Ensure transportation equipment, tools, and safety supplies are available, maintained, and used appropriately by staff.

• Provide daily leadership, scheduling, and operational oversight to drivers and transportation staff.
• Support recruitment, onboarding, training, and performance management processes in collaboration with the People and Culture team and leadership.
• Ensure drivers and transportation staff are trained on safe driving practices, vehicle operation, routing procedures, equipment use, and regulatory compliance requirements.
• Manage staffing schedules, attendance, and operational coverage to align with organizational needs and transportation demands.
• Approve timecards and maintain…