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.

Duties And Responsibilities

Fleet & Transportation Operations

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.

Health & Safety

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.

Fleet Maintenance & Equipment Management

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.

Team Leadership and Employee Supervision

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 accurate scheduling records in accordance with organizational practices. Utilize fleet tracking and communication systems to support route efficiency, team coordination, and service responsiveness. Maintain regular communication with the Logistics and Donation Centre Manager to address team performance, logistics challenges, and resource needs. Ensure drivers and transportation team provide professional and positive customer service during donation pickups, deliveries, and community interactions.

Operational & Cross-Departmental Support

Support distribution and logistics operations through coordination of deliveries, pickups, and transportation requirements across the organization. Maintain effective communication with warehouse, retail, and program teams regarding transportation schedules, operational updates, and logistics requirements. Provide operational support across departments as required to support organizational efficiency and continuity of service. Support volunteer participation in transportation and logistics-related activities as required.

Other duties as required

Requirements

Education

College education in transportation, logistics, supply chain management, or a related field, or equivalent combination of education and experience Forklift operating certification is required Valid driver’s license with an acceptable driving record is required.

Experience

Minimum 5 years of transportation, fleet, logistics, or warehouse operations experience Minimum 1-2 years of leadership or transportation, logistics, warehouse, or operational settings. Experience coordinating fleet maintenance, transportation scheduling, and driver operations preferred. Experience working in fast-paced operational environments with changing priorities and deadlines.

Skills & Competencies

Strong understanding of transportation operations, fleet coordination, and workplace safety practices. Strong organizational, planning, and problem-solving skills with the ability to prioritize multiple tasks in a fast-paced operational environment. Effective verbal and written communication skills in English. Strong leadership, interpersonal, and decision-making skills with the ability to build and maintain positive working relationships with employees, leadership, donors, customers, volunteers, and community stakeholders. Excellent customer and donor service skills with a professional and approachable demeanor. Demonstrated understanding of and alignment with the WINS mission, values, and commitment to supporting program participants, customers, donors, volunteers, and the community. Eligible to legally work in Canada. Must be able to provide satisfactory results of a Criminal Record Check.

Physical Demands & Working Conditions

This is a hands-on, working manager role that actively supports transportation, delivery, and logistics operations as required. The Fleet Manager may be required to operate delivery vehicles, complete delivery routes, or assist with pickups and deliveries during staffing shortages or operational demands. Ability to safely work in warehouse, loading dock, retail, and outdoor environments in varying weather conditions. Physically capable of standing, walking, bending, climbing in and out of trucks, and performing repetitive physical tasks for extended periods throughout the workday. Able to safely and consistently lift and move up to 50 lbs (23 kg) independently and up to 100 lbs (45 kg) as part of a team on a regular and ongoing basis. Comfortable performing frequent loading and unloading of goods and working extended periods on delivery routes when required. Must be able to safely operate equipment and vehicles in accordance with WINS safety standards and transportation regulations.