Director, Transportation Operations & Maintenance

Job ID: 62034
Job Category: Operations & Maintenance
Division & Section: Transportation Services, Winter & Seasonal Services and Maintenance & Delivery Services
Work Location: City Hall, 100 Queen St. E, Toronto, ON, M5C 1S6
Job Type & Duration: Permanent, Full-Time
Salary Range:$162,467 – $215,307 TM2479, Wage Grade 10
Hiring Zone:$170,471 – $184,826
Shift Information: Monday to Friday, 35 hours per week
Affiliation: Non-Union
Number of Positions Open: 2
Posting Period: 04-Mar-2026 to 24-Mar-2026

The City of Toronto’s Transportation Services Division is committed to building and maintaining a resilient, safe, and well managed transportation network that keeps people connected to the places, activities, and communities they value.

Transportation Services is currently recruiting two Director positions for the following sections through this job posting:

Winter & Seasonal Services

The Director, Transportation Operations & Maintenance (Winter & Seasonal Services) oversees the City’s winter operations, street cleaning, grass cutting, minor road and sidewalk repairs, mapping and analytics, landscape maintenance, and support for programs like CaféTO and special events.

Maintenance & Delivery Services

The Director, Transportation Operations & Maintenance (Maintenance & Delivery Services) oversees the delivery and inspection of maintenance and capital projects, signage and pavement markings, and traffic and lighting systems.

The successful candidates for these roles bring strategic vision, strong political acuity, a commitment to public service, and the ability to lead high-performing teams in a dynamic unionized environment. They also have a demonstrated ability to lead modernization initiatives that enhance systems, processes, and sectional performance to support safe, reliable roads, sidewalks, bikeways, and related assets.

Major Responsibilities

The primary functions associated with these roles are, but not limited to:

Operations & Service Delivery

Provides strategic oversight of city-wide road operations, maintenance activities, and winter operations to ensure safe, reliable, and efficient service delivery.
Provides strategic oversight of the construction, maintenance, and asset management of traffic control and lighting systems, ensuring reliable operations and supporting services such as graffiti removal and infrastructure locates.
Identifies and resolves operational issues affecting communities and mobility, ensuring timely, coordinated responses and strong service outcomes.
Champions safe work practices, quality assurance, and consistent operational standards across all operations and maintenance activities.
Ensures all divisional activities comply with the Occupational Health and Safety Act, City policies, regulatory standards and applicable legislation.

Strategy & Performance Management

Leads the development and execution of long-term strategies, policies, and modernization initiatives that strengthen divisional performance and align with corporate priorities.
Champions continuous improvement and change management efforts, advancing innovation, operational excellence, and data informed decision making across the Division.

Financial & Risk Management

Leads multi year capital and operating budget planning, forecasting, and monitoring to ensure effective stewardship of public resources.
Establishes financial controls, resource allocation frameworks, and risk management systems that support accountability and informed decision making.
Drives effective and efficient contract procurement, management and compliance.
Leads the review of Auditor General findings and implementation of system and process improvements to strengthen contract management and enhance service delivery.

Strategic Leadership & Partnership

Leads, motivates, and develops a large, diverse unionized workforce, fostering a culture of inclusion, innovation, and continuous improvement.
Promotes effective labour management relations by ensuring compliance with collective agreements and supporting constructive, collaborative engagement.
Builds strong partnerships and fosters collaboration across City divisions, Agencies, Boards & Commissions, and external stakeholders to advance shared priorities and identify opportunities for innovation, service improvement, and operational efficiency.
Represents the Division at Council, Standing Committees, Community Councils, and public forums, providing advice and strategic leadership on transportation operations and policy.
Represents the Transportation Services Division in responding to inquiries from the media, elected officials, and the public, ensuring clear and consistent communication on divisional matters, initiatives, and decisions.

Key Qualifications:

Post-secondary education in a discipline relevant to the role, or an equivalent combination of education and experience.
Extensive progressive experience leading large, complex infrastructure operations and program delivery in the public‑sector or comparable environment. Experience in the transportation industry is an asset.
Extensive experience in contract development, management, and evaluation within the public sector or comparable environment.
Extensive experience leading complex projects and organizational change, including process improvement, business re‑engineering, and implementing modernization strategies.
Demonstrated ability to lead diverse, multidisciplinary teams while fostering an inclusive, high‑performing workplace culture grounded in equity, diversity, inclusion, and reconciliation.
Demonstrated financial and business acumen, including expertise in budget development, operational planning, and the use of tools and practices that enhance efficiency and support effective service delivery.
Exceptional political acuity, with the ability to navigate complex political environments, effectively engaging elected officials, senior leadership, and diverse stakeholders while managing competing goals and priorities.
Highly developed communication and interpersonal skills, with the ability to negotiate effectively, resolve conflicts, and apply sound problem‑solving approaches within a complex unionized environment.
Proven ability to effectively build and maintain collaborative working relationships with a wide range of stakeholders, including employees, unionized staff, client divisions, external agencies, elected officials, and other orders of government within a large, diverse, and multidisciplinary environment.
Comprehensive knowledge of relevant legislation and regulations related to municipal governance, transportation sector (i.e. Ontario Highway Traffic Act, Ontario Traffic Manual), budgeting and financial reporting, employee and labour relations, and occupational health and safety.

Note To Current City of Toronto Employees
City of Toronto employees are eligible to apply for the posted job opportunity, but cannot hold two different jobs. To be considered for this job posting, you must indicate that you are a “Current City of Toronto employee” on the on-line application form, and provide your “Employee Number”.

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.

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