Delivery Supervisor jobs in Toronto, ON

Job Overview

The Assistant Manager – Fleet & Driver Manager is responsible for the day-to-day and overnight delivery operations of Circles & Squares. This role owns the driver team, the truck fleet, and the routing and execution of all customer deliveries at night. The successful candidate will optimize routes, drive labour and fuel efficiencies, uphold safety and regulatory compliance (including CVOR), and ensure every customer order is delivered accurately and on time. This is a hands-on leadership role: the manager is expected to ride along on occasional night routes to identify route and driver efficiencies firsthand.

Key Responsibilities

Delivery Routes & Routing

• Own and manage all Circles & Squares night delivery routes end to end.
• Plan, build, and continuously optimize customer routing for cost, speed, and reliability.
• Adjust routes proactively for volume changes, new customers, seasonality, traffic, and weather.
• Ride along on occasional night routes to identify route and driver efficiencies firsthand.

Driver Team Leadership

• Lead, schedule, and supervise the team of delivery drivers across night shifts.
• Set performance expectations, provide coaching, and handle day-to-day people issues.
• Onboard and train new drivers on routes, equipment, safety, and company standards.
• Monitor driver behaviour and conduct on-route and loading-time observations.
• Identify labour savings during loading and while on route, without compromising service or safety.

Delivery Execution & Customer Service

• Own resolution of delivery issues and errors — shorts, damages, late or missed deliveries, and misdeliveries.
• Track recurring delivery problems and put corrective measures in place to prevent repeats.
• Coordinate with the catering department to ensure smooth daytime customer deliveries.
• Act as the escalation point for time-sensitive or high-priority customer delivery needs.

Fleet Management

• Assist to Manage the fleet of trucks: cleanliness, servicing, maintenance, and repairs.
• Maintain a preventive maintenance schedule to minimize downtime and breakdowns.
• Keep all fleet documentation and paperwork accurate, organized, and up to date.
• Track fleet costs (fuel, maintenance, repairs) and flag opportunities for savings.

Food Safety & Temperature-Controlled Delivery

• Be well versed in food safety practices, given the bakery’s refrigerated and temperature-sensitive products.
• Ensure refrigerated trucks hold proper temperature ranges during loading, transit, and delivery.
• Monitor and log refrigeration temperatures, and respond promptly to any excursions or equipment issues.
• Train drivers on food safety and cold chain handling procedures for temperature-sensitive deliveries.

Safety & Compliance

• Assist in ensuring CVOR (Commercial Vehicle Operator’s Registration) rules are met by drivers and the fleet.
• Monitor hours of service, licensing, inspections, and driver/vehicle records for compliance.
• Promote a strong safety culture and ensure adherence to road safety and company policies.
• Support incident reporting and follow-up for accidents, near-misses, and violations.

Continuous Improvement & Reporting

• Analyze route, labour, and fleet data to surface efficiency and cost-saving opportunities.
• Recommend and implement process improvements across routing, loading, and delivery.
• Report regularly to the Logistics Manager on performance, issues, and savings achieved.

Requirements

• Proven experience in logistics, distribution, fleet, or delivery operations, ideally with team leadership.
• Strong knowledge of route planning and optimization.
• Familiarity with CVOR requirements and commercial vehicle compliance (or ability to learn quickly).
• Valid driver’s licence; ability to operate or ride along in company delivery vehicles as needed.
• Comfortable working occasional overnight shifts to observe and improve night routes.
• Solid people-management skills — coaching, scheduling, and accountability.
• Detail-oriented with sound documentation and record-keeping habits.
• Well versed in food safety and cold-chain handling practices for refrigerated, temperature-sensitive products.
• Customer-focused, with strong problem-solving under time pressure.

Key Competencies

• Operational ownership and accountability
• Efficiency and cost-consciousness
• Safety and compliance mindset
• Clear communication and team leadership
• Hands-on, willing-to-ride-along work ethic
• Ability to work occasional night shifts

Working Condition

This role combines office/planning work with hands-on, on-the-ground operations. It includes time in the yard and trucks, occasional overnight route ride-alongs, and coordination across the bakery, catering, and wholesale operations. Some early mornings, late nights, and flexibility around delivery schedules should be expected.

Pay: $60,000.00-$70,000.00 per year

Work Location: In person