Supervisor (Seasonal – Winter Maintenance)

Description: A.&F. Di Carlo Construction Inc. is seeking dedicated and experienced Winter Maintenance Supervisors to oversee and coordinate municipal winter maintenance operations across Toronto. The Winter Maintenance Supervisor will oversee roadway and sidewalk plowing and salting, anti-icing, bike lane maintenance, snow removal, and other winter maintenance activities. The Supervisor will be responsible for coordinating personnel and operational resources, supporting Dispatch, monitoring field activities and equipment readiness, and ensuring contractual service levels and operational requirements are achieved. The ideal candidate is a competent and proactive supervisor with extensive experience in municipal winter maintenance operations. They will possess strong leadership, organizational, operational planning, and decision-making skills, with the ability to effectively organize, direct, monitor, and document field operations; supervise crews; coordinate staffing and operational resources; resolve operational and logistical issues; enforce health and safety legislation, company policies, and contractual requirements; and ensure winter maintenance services are completed safely, efficiently, and in accordance with required service levels and applicable standards. The successful candidate must be able to respond effectively to changing weather and operational conditions and maintain shift flexibility for the duration of the winter maintenance contract, as required based on significant weather events and operational needs.

Key Responsibilities:

• Utilize knowledge of assigned contracts to plan and supervise municipal winter maintenance operations, ensuring contractual service levels, timelines, and operational requirements are achieved.
• Supervise winter maintenance operations, including roadway and sidewalk plowing and salting, anti-icing, bike lane maintenance, snow removal, and winter training activities.
• Organize, oversee, monitor, and enforce winter maintenance operations in accordance with the Occupational Health & Safety Act (OHSA), company policies and procedures, contractual requirements, and all applicable legislation.
• Lead and supervise personnel by monitoring performance, attendance, conduct, training, development, discipline, competency, and fitness for duty, while clearly communicating service level and operational expectations.
• Support Dispatch by coordinating staffing requirements, standby and call-in procedures, workforce deployment, and operational readiness before and during winter weather events.
• Monitor winter maintenance field activities before, during, and after weather events and training activities, identify operational or logistical issues, and coordinate or implement corrective actions to maintain safe, efficient, and compliant service delivery.
• Maintain a safe work environment by identifying hazards, implementing corrective actions, enforcing health and safety requirements, conducting and documenting hazard assessments, site inspections, safety talks, and incident and accident investigations, and maintaining required health and safety documentation.
• Monitor fleet and equipment utilization and operational readiness, ensuring required pre-trip inspections are completed and identified deficiencies are addressed promptly. Support operational performance, accountability, and contract compliance through the effective use of company GPS, Routeware, and other applicable systems. Monitor and maintain salt inventories and ensure timely and effective communication with internal and external stakeholders.
• Monitor field operations to ensure quality, productivity, site organization and control, regulatory compliance, and timely resolution of operational, client, municipal, and public concerns.
• Ensure all required payroll, attendance, operational, inspection, incident, fleet, inventory, and other company documentation and records are accurately completed and maintained within established timelines.
• Participate in daily operational meetings, as well as internal, client, external, and other required meetings, providing operational updates and carrying out assigned responsibilities.
• Communicate professionally and effectively with employees, Dispatch, Management, stakeholder representatives, contractors, and clients.
• Maintain shift flexibility and availability for the duration of the winter maintenance contract, as required based on significant weather events and operatio…