Fleet Team Lead

Overview

The Fleet Team Lead plays a key operational support role at the WINS Donation Centre, helping ensure the safe, timely, and efficient external movement of goods from the Donation Centre to WINS’ retail stores and programs, as well as supporting the pickup of donations from donors and partners. Reporting to the Fleet Manager and working closely with the Fleet Assistant Manager, this role provides hands-on leadership to the truck and moving team and supports daily routing, loading/unloading, and delivery execution.

This position is critical to maintaining reliable transportation services that support store performance and program fulfillment in alignment with WINS’ mission of providing women and their families with the resources to thrive. The Team Lead reinforces safety practices, supports equipment readiness, and helps ensure a professional, donor- and customer-focused experience during pickups and deliveries.

Duties And Responsibilities

Outbound Distribution & Logistics (External)

• Support daily and weekly routing and delivery plans for WINS trucks in alignment with organizational priorities and operational requirements.
• Assist with adjustments to pickup and drop-off schedules in response to changes from donors, program participants, or store/warehouse teams.
• Communicate clearly and consistently with retail stores and Donation Centre teams to coordinate inventory movement, timing, and delivery expectations.
• Lead and support safe, accurate loading of trucks and ensure deliveries are completed in a timely and organized manner.
• Ensure goods are secured properly (straps, safe stacking, load balance) and handled in ways that reduce damage and loss.
• Support donation pickups and deliveries to program participants as needed, ensuring professional and respectful service at all sites.
• Support safe and compliant transport of recyclable and non-recyclable goods as directed.

Team Leadership & Daily Coordination

• Provide daily task direction and on-shift leadership to drivers and moving associates to ensure work is completed safely and to standard.
• Support onboarding and training of new team members on routes, delivery protocols, donor pickup expectations, customer service standards, equipment use, and safety procedures.
• Monitor workflow progress during shifts and help ensure tasks are completed on time and to standard.
• Provide coaching, feedback, and real-time support to maintain efficient service and positive team performance.
• Keep the Fleet Manager and Fleet Assistant Manager informed of operational issues, route challenges, and resource needs.

Health & Safety

• Reinforce compliance with all transportation-related health and safety policies, procedures, and safe work practices.
• Monitor and model proper PPE use and safe work practices in loading zones, docks, store deliveries, and donor sites.
• Support regular safety checks and housekeeping in truck bays/loading areas; address hazards promptly.
• Support incident reporting, follow-up, and training as directed by the Fleet Manager, Fleet Assistant Manager, or Health & Safety team.
• Foster a strong safety culture through communication, coaching, and leading by example.

Equipment Maintenance (Fleet)

• Support daily vehicle readiness by completing and verifying pre-use inspections and ensuring trucks and equipment (lifts, straps, dollies, pallet jacks) are clean, available, and safe.
• Identify and report mechanical or equipment concerns promptly; support coordination of repairs and preventative servicing to minimize downtime.
• Support accurate completion of vehicle inspections, maintenance records, and required documentation, escalating maintenance needs to the Fleet Manager or Fleet Assistant Manager as required.

Volunteer Engagement (As Applicable)

• Support coordination of volunteers involved in logistics-related activities such as donation drives, deliveries, and Donation Centre events.
• Ensure volunteers are welcomed, oriented on safety procedures, and assigned meaningful tasks aligned with their capacity and availability.
• Contribute to a positive, inclusive volunteer experience aligned with WINS’ values.

Operational Support Across Departments

• Provide operational support to Inventory and Sort teams as business needs require, helping maintain workflow continuity across the Donation Centre.
• Contribute to cross-departmental collaboration and shared accountability for workplace safety and operational effectiveness.

Acting Coverage / Continuity

• Provide continuity and on-shift leadership for truck/distribution operations when the Fleet Assistant Manager and Fleet Manager are unavailable.
• Escalate operational exceptions, staffing concerns, and safety issues to the Fleet Assistant Manager and/or Fleet Manager
• Document operational updates, shift outcomes, safety concerns, and required follow-up actions to ensure continuity between shifts.
• Other duties as required.

Requirements

Education

• Grade 12 diploma or equivalent combination of education and experience.
• Forklift operating certification is required.

Experience

• Minimum 2 years of transportation, logistics, fleet, warehouse, or distribution experience.
• Minimum 1 year of supervisory or leadership experience in an operational environment.
• Experience in a nonprofit, social enterprise, or community-based organization is considered an asset.
• Experience working in fast-paced operational environments with changing priorities and deadlines.

Skills & Competencies

• Must be legally eligible to work in Canada.
• Demonstrates an understanding of and commitment to the WINS mission, values, and role in supporting clients, customers, volunteers, donors, and the community.
• Strong organizational and time management skills with the ability to prioritize multiple tasks in a fast-paced environment.
• Excellent verbal and written communication skills in English.
• Basic numeracy skills to support inventory control and operational accuracy.
• Welcoming, respectful, and empathetic approach with the ability to build positive relationships with staff, volunteers, donors, and customers.
• Strong customer and donor service orientation.
• Flexible and able to work a variety of shifts between Sunday and Saturday, typically between 7:30 a.m. and 4:00 p.m., including weekends on a rotating basis.
• Must wear CSA-approved steel-toed safety boots while on duty.

Physical Demands & Working Conditions

• Work is performed in warehouse and outdoor environments with regular exposure to varying weather conditions, moving vehicles and equipment, noise, dust, and other operational hazards.
• Requires frequent standing, walking, bending, kneeling, reaching, and climbing throughout the shift.
• Must be able to safely lift and carry up to 50 lbs (23 kg) independently and up to 100 lbs (45 kg) with team assistance.
• Requires the ability to load, unload, inspect, and move donated goods, equipment, and fleet-related materials.
• Required to operate company vehicles and travel between WINS locations as operationally required.
• Must be able to work safely while using material handling equipment and comply with all health and safety policies, including the use of required personal protective equipment (PPE).
• Occasional overtime, weekend work, or schedule adjustments may be required to meet operational needs.