Supervisor, Works Contracted Services

Job Details: Permanent Full Time (Non-Union)

Posting Status: Open to all current Town of Oakville employees and external applicants

Closing Date: Applications for this position must be received at oakville.ca by no later than 11:59 pm on October 8, 2026.

This job posting is for an existing vacancy and therefore will be filled accordingly.

We offer:

A defined benefit pension plan (OMERS)

Comprehensive health plan complemented with life and disability insurance

A progressive work environment that promotes a work/life balance and strives to be a great place for great people to do great things

What can I expect to do in this role? Reporting to the Manager, Works Operations, the Supervisor, Works Contracted Services is responsible for providing expert guidance and contract oversight across the Town’s right-of-way maintenance operational contracts and small capital infrastructure rehabilitation initiatives, while ensuring these are delivered within approved scope, schedule, budget, quality and the Town’s safety requirements.

In this role, you will:

Oversees the successful delivery of the Town’s right-of-way operational contracts (i.e. Winter Control, loose-leaf collection, yearly sidewalk replacement program, etc.) and small capital rehabilitation projects (i.e. minor storm sewer replacements, retaining walls, bridge repairs and multi-use pathways) from planning through completion.

Ensures operational and capital budget delivery and compliance, and that projects stay within approved budget while following municipal rules, provincial laws, and applicable regulations.

Prepares and develops contracts, scope, drawings, specifications, and contract conditions.

Oversees procurement planning, prepares and awards tenders, prepares project award reports, and assists with tender documentation, scopes of work, contract negotiation and contractor evaluations.

Provides leadership, oversight, and support to staff undertaking contract administration activities, including contractor management, compliance monitoring, dispute resolution, change control, claims management, payment approvals and project closeouts.

Provides oversight and guidance on the review of engineering designs for Regional, Town, and external stakeholder projects (i.e. Metrolinx, developments) to ensure functionality, operational requirements, and operational maintenance standards can be met.

Oversees roadway patrol and sidewalk inspection programs to ensure compliance with Ontario Minimum Maintenance Standards (O.Reg. 239/02) and maintain accurate, defensible records for claims management.

Leads and develops a multidisciplinary team of Project Leaders, Inspectors, Operations Technologists and Infrastructure Technicians through strategic workload planning, performance management, mentorship including performance assessment, and career/skillset development initiatives.

Supports workforce planning through recruitment, onboarding, training, coaching, and maintenance of job documentation.

Provides operational leadership and technical support, including staff coverage, after-hours standby participation, acting for the Manager during absences, and representing the Town in claims-related matters.

Supports in identifying and implementing improvements to operational practices, contract delivery, and service performance, while maintaining industry partnerships and engagement.

Serves as a primary representative for Works Operations customer complaints, escalated service requests, Council inquiries and stakeholder concerns.

Performs other duties as assigned.

How do I qualify?

Diploma in Civil Engineering Technology, Construction Engineering Technology, or a related technical discipline, combined with a Certified Engineering Technologist (C.E.T.) designation. A Bachelor of Engineering (B.Eng.) or Bachelor of Architecture (B.Arch.) degree would be considered an asset.

Minimum 8 years of progressively responsible experience in municipal, provincial, or private sector infrastructure construction, maintenance, and rehabilitation program delivery, including contract preparation, procurement/tendering, contract administration, and design review.

Experience in managing right-of-way projects including asphalt applications, stormwater management, concrete surfaces and other municipal or infrastructure operations maintenance activities.

Experience with winter operations, loose leaf collections, or other operations and maintenance programs is an asset.

Experience leading teams responsible for infrastructure construction, maintenance or operational programs.

Proven ability to manage projects and supervise staff across all areas of infrastructure construction, maintenance, and operations.

Exceptional interpersonal, commu