Job Description

Job ID: 66340

Job Category: Maintenance & Delivery

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

Shift Information: Monday - Friday, 40 Hours Per Week

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:

1. Post-secondary degree or diploma in Civil Engineering/Civil Engineering Technologist/Technician
2. and/or the equivalent combination of education and experience.
3. Extensive experience managing and administering contracts, as well as conducting inspections of installations, materials, and methods of construction.
4. Considerable experience leading, planning and providing work direction for technical and administrative staff, contractors, and consultants in a unionized and/or non-union environment.
5. Experience in the principles of winter maintenance and its various applications as it relates to municipal service delivery.
6. Must possess and be able to maintain a valid Province of Ontario class "G" driver's licence and be eligible to qualify for a City driver's permit including the ability to drive during various inclement weather conditions.

The candidate should also have:

1. Customer service, conflict management and interpersonal skills to resolve issues and customer service complaints from staff, members of the public, contractors and external agencies including utility companies.
2. Proficient computer skills to utilize a variety of software including Microsoft Office Suite (e.g. Word, Excel, PowerPoint and MS Outlook) with the ability to use SAP, Maximo, and RACS (Road Allowance Control System and or other municipal maintenance management or budget systems would be an asset.
3. Knowledge of relevant legislation, regulations, codes, collective agreements and policies including City of Toronto Standards and Specifications for road works, Ontario Provincial Standards and Specifications (OPSS), the Construction Act, Occupational Health and Safety Act, Employment Standards Act and other applicable legislation.
4. Ability to read and interpret technical drawings, specifications and reports.
5. Ability to work beyond normal business hours, including on standby, nights and weekends including various shifts and drive in inclement weather conditions.
6. Ability to effectively represent the Division and to maintain relations and work with community and interest groups, the general public, elected officials, internal and external clients and consultants.
7. Experience with AutoCAD, Microstation, Bluebeam, SketchUp, and/or ArcGIS or QGIS would be considered an asset.

Equity, Diversity and Inclusion

The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve. Learn more about the City’s commitment to employment equity

Accommodation

The City of Toronto is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code-protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. Disability-related accommodation during the application process is available upon request Learn more about the City’s Hiring Policies and Accommodation Process