Supervisor Maint Contract Inspections

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Division & Section: Transportation Services, Maintenance & Delivery Services

Work Location: 8270 Sheppard Ave

E.

Job Type & Duration: Full-time, Permanent

Salary Range
: $89,337 – $132,880

Affiliation: Non-Union

Number of Positions Open
: 1

Posting Period: 17-AUG-2026 to 28-AUG-2026

The Transportation Services Division’s Maintenance & Delivery is seeking an experienced Supervisor of Maintenance Contract Inspections to join the team.

In this role, you will supervise and train inspection staff responsible for day-to-day contract delivery summer and winter operations and support the preparation and issuing of contracts. You will also oversee the contract administration for critical city contracts that ensure the maintenance of Toronto’s public rights-of-ways, including streets, bikeways, and sidewalks. In this role, you will support the delivery of essential road operations services and conduct a larger ongoing review of the division’s service delivery approach.

This is an exciting time to join the Maintenance & Delivery Section, which is leading the transformation of Toronto’s maintenance and delivery operations. The Section’s major initiatives include multi-modal winter maintenance, road, sidewalk, and bikeway repairs, capital construction contract development, delivery, inspection, and the installation and maintenance of signage and pavement markings. The CCDI unit is at the forefront of delivering operating and capital programs with a strong focus on cost efficiency, sustainability, equity, and multi-modal transportation solutions.

Major Responsibilities:

As a Supervisor, you will oversee Maintenance Patrollers and Inspectors of Municipal Construction staff to deliver annual and ongoing maintenance contracts. Key contracts include critical interim repairs, paver repairs, small-scale civil improvements and capital projects, quick build bikeways, expressway and bridge maintenance, emergency contract responses, and winter operations like snow clearing and salting.

In this role, you will supervise, motivate, and train staff, fostering teamwork and continuous learning. Daily oversight will include scheduling, assigning tasks, reviewing work, approving time off, monitoring performance, promoting continuous learning, and fostering innovation. More occasionally, as a Supervisor, you could hear grievances in accordance with the collective agreement and recommend disciplinary actions.

Budget and contract management will be a major focus of this role. You will lead and support preparing and administering budgets and scopes for summer and winter contracts, monitoring compliance, and ensuring quality. As a Supervisor, you will oversee construction inspections for City projects delivered by third-party contractors. Contract management responsibilities will include conducting pre-construction and progress meetings, maintaining contract records, and ensuring compliance with audit requirements.

In this role, you will frequently engage with members of the public, inter-divisional partners, elected officials, and other stakeholders, including addressing service requests and inquiries originating from the City’s 311 system. Strong communication skills are essential for resolving disputes with staff, stakeholders, the public, officials, contractors, and utility representatives. Your ability to clearly convey technical concepts to non-technical audiences will foster collaboration, build trust, and ensure informed decision-making.

There are regular emergency and seasonal duties. As a Supervisor, you will need on-call availability.

Key

Qualifications:

• Post-secondary degree or diploma in Civil Engineering/Civil Engineering Technologist/Technician
• and/or the equivalent combination of education and experience.
• Extensive experience managing and administering contracts, as well as conducting inspections of installations, materials, and methods of construction.
• Considerable experience leading, planning and providing work direction for technical and administrative staff, contractors, and consultants in a unionized and/or non-union environment.
• Experience in the principles of winter…