At Flanagan Foodservice, we're more than just the biggest family-owned food distributor in Canada; we're a dynamic hub of innovation, creativity, and a shared passion for delivering exceptional service.

For nearly 50 years, we've been on an exciting journey of growth and transformation. The foodservice landscape is thrilling and challenging, and as we reshape our business, we're on the hunt for imaginative minds, business strategists, and food lovers.

JOB DESCRIPTION

Position Title: Fleet Safety & Training Compliance Supervisor

Department: Transportation

Position Reports to: Fleet Manager

Position Summary:
The Fleet Safety & Training Compliance Supervisor plays a key leadership role within Flanagan Foodservice’s transportation network, combining operational oversight with company-wide driver development and training responsibilities. This position directly supervises company drivers at their home branch (either Kitchener or Whitby) and provides functional leadership to the Fleet Training Coordinators responsible for driver onboarding, safety, and compliance across all three branches—Kitchener, Whitby, and Sudbury. The successful candidate will ensure that transportation operations run efficiently, safely, and in compliance with Ministry of Transportation (MTO) and company standards while fostering a culture of continuous improvement, professional development, and operational excellence.

Key Responsibilities:
Operational Leadership

• Provide daily supervision, direction, and performance management for drivers at the home branch (Kitchener or Whitby).
• Support driver scheduling, route coverage, vacation planning, and equipment allocation to meet service and cost objectives.
• Ensure on-time, accurate, and compliant deliveries in accordance with MTO regulations and internal safety standards.
• Conduct driver coaching, performance discussions, and engagement visits to promote accountability, service excellence, and morale.
• Investigate accidents, safety incidents, and compliance violations, ensuring appropriate follow-up and documentation.
• Collaborate with Routing, Fleet Maintenance, and Operations to maximize utilization, reduce overtime, and enhance efficiency.
• Ensures all Food Safety policies, procedures and HACCP guidelines are followed.
• Ensures timely follow-up with all required corrective and preventative actions as needed.
• Implements and enforces safety protocols in compliance with the OHSA regulations to ensure a safe and secure environment for all employees.
• Provides support to the employees and ensure the accurate and timely reporting for injuries and accidents, and collaborates with Health & Safety to implement effective countermeasures.
• Provides support and work in collaboration with Health & Safety on the Early and Safe Return to Work Program.
• Conducts, assists with Health & Safety workplace observations.

Fleet Training & Compliance Leadership

• Supervises and provide direction to the Fleet Training personnel across Kitchener, Whitby, and Sudbury branches.
• Oversees the consistent execution of all onboarding, orientation, refresher, and re-certification training programs.
• Ensure compliance with CVOR, OHSA, and Flanagan’s internal safety, food safety, and operational policies.
• Leads initiatives that improve driver competency, retention, and overall safety performance.
• Supports the rollout of new technologies and tools (dash cameras, telematics, route optimization systems).
• Maintains up-to-date training documentation, driver files, and performance tracking systems.
• Develop, enhance, and standardize training content across branches to ensure consistency in expectations and delivery quality.

Employee Development & Engagement

• Coaches, mentors, and develops both drivers and Fleet Training personnel through regular feedback and structured evaluations.
• Fosters an environment that values continuous learning, accountability, and professional growth.
• Promote a safety-first, customer-focused culture aligned with Flanagan’s Vision, Mission, and Values.
• Collaborates cross-functionally with Inbound, Warehouse, and HR teams to ensure alignment on operational goals and people development.

Required Qualifications:

• College Diploma or University Degree in Transportation, Logistics, or Business preferred.
• Minimum 5 years of experience in transportation or logistics with at least 2 years in a leadership/coaching or training capacity.
• Valid AZ license and clean driving record required.
• In-depth understanding of MTO, CVOR, and OHSA compliance standards.
• Experience developing and facilitating driver-training programs and applying adult learning principles.
• Strong analytical, planning, and communication skills with demonstrated leadership capability.
• Proficiency with Microsoft Office, Omnitracs, Shaw, Roadnet, and other transportation or fleet management systems.
• Proven ability to balance people leadership with operational performance management.

Unique Requirements:

• Must be flexible to travel between Kitchener, Whitby, and Sudbury as required
• Willing to work early mornings or extended hours to support training or operational needs.
• Adherence to all HACCP, Food Safety, and Health & Safety standards.
• Ability to work effectively under pressure while maintaining professionalism and composure.

Be Part of the Legacy!

All employees of Flanagan Foodservice must demonstrate adherence to all Health & Safety and Food Safety practices as well as all Company’s policies and procedures.

Flanagan Foodservice Inc. is an equal opportunity employer, and has an accommodation process in place to provide accommodations for applicants with disabilities. If you require a specific accommodation because of a disability or a medical need, please let us know by submitting your request to accessibility@flanagan.ca so that arrangements can be made for the appropriate accommodations.