Construction & Winter Maintenance Supervisor (Year-Round)

A&F Di Carlo Construction Inc. is seeking a dedicated and experienced Construction & Winter Supervisor to oversee year-round municipal operations within Toronto. Reporting directly to Executive Management, this position is responsible for providing frontline supervision of municipal construction and winter maintenance operations, with a primary focus on Health & Safety leadership, regulatory compliance, crew supervision, documentation, inspections, and enforcement of company policies. The role also supports the planning, coordination, and execution of daily operations to ensure contractual obligations are met safely, efficiently, and in accordance with company standards.

During the construction season, the successful candidate will supervise municipal asphalt, concrete, grading, and road rehabilitation projects, with Health & Safety serving as the primary focus. Responsibilities include monitoring field activities, conducting inspections, enforcing legislative and company requirements, maintaining operational documentation, supervising crews, and supporting daily project coordination. During the winter season, the role transitions to supervising municipal winter maintenance operations, including snow plowing, salting, anti-icing, and snow removal services, while ensuring compliance with all operational, health and safety, contractual, and legislative requirements. The role requires shift flexibility throughout the winter maintenance contract to respond to significant weather events and changing operational needs.

The ideal candidate is a competent and proactive supervisor with extensive experience in municipal construction and winter maintenance operations. They will possess strong leadership, organizational, and decision-making skills, with the ability to effectively organize, direct, monitor, and document field operations; supervise crews; enforce Health & Safety legislation, company policies, and contractual requirements; and ensure work is completed safely, efficiently, and in compliance with all applicable standards.

Duties & Responsibilities:

General Duties

• Successfully attend and complete all required training related to A&F Di Carlo Construction’s operational standards, health and safety requirements, compliance policies, and company procedures, and participate in daily operational meetings, as well as internal, client, external, and other meetings as required.
• Accurately record hours worked using the company’s timekeeping system. Review and submit staff hours and required payroll information to Payroll on a daily basis, and investigate and resolve payroll discrepancies as required.
• Perform supervisory duties as a competent person by organizing, overseeing, monitoring, and enforcing construction and 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 supporting Foremen during construction operations, Dispatch during winter maintenance operations, and Management year-round.
• 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. Participate in Joint Health & Safety Committee (JHSC) activities as required. Utilize company-designated health and safety mobile applications, forms, and programs to complete and maintain required documentation.
• Monitor field operations to ensure quality, productivity, site organization and control, regulatory compliance, and timely resolution of operational, client, municipal, and public concerns, while ensuring all required payroll, attendance, operational, inspection, incident, fleet, procurement, inventory, and company documentation is accurately completed and maintained within established timelines.
• 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 appli…