Manager Transportation Operations & Maintenance (CLAIMS AND INVESTIGATIONS)

Position Details

• Job Category: Operations & Maintenance
• Division & Section: Transportation Services, Winter and Seasonal Services
• Work Location: 64 Murray Road, North York
• Job Type & Duration: Full-time, Temporary, 12 month Vacancy
• Shift Information: Monday to Friday, 35 hours per week
• Posting Period: 01-Sep-2026 to 22-Sep-2026
• Affiliation: Non-Union

Job Summary

Guided by a vision to provide a safe, efficient and effective transportation system that serves residents, businesses and visitors in an environmentally, socially and economically sustainable manner, the Transportation Services Division plans, constructs and manages transportation infrastructure within Toronto’s public right-of-way, including roads, sidewalks, cycling infrastructure, bridges and laneways.

If you are a strategic, politically astute operations leader with experience in transportation operations, risk management, claims, investigations, and municipal service delivery, this is an exciting opportunity to join Transportation Services as Manager, Transportation Operations & Maintenance.

Major Responsibilities

• Provide strategic oversight of road maintenance, winter operations, emergency response, claims, and risk mitigation activities.
• Lead and develop multidisciplinary teams.
• Manage operational and financial resources.
• Foster strong stakeholder relationships and ensure safe, efficient, compliant, and customer-focused service.
• Provide strategic and operational leadership for city-wide claims management, right-of-way patrol, field investigation, inspection, and emergency response functions.
• Oversee claims investigations, field operations, and infrastructure monitoring programs by establishing standards, performance measures, and risk management practices.
• Ensure compliance with legislative, legal, and records management requirements.
• Oversee complex and high-risk claims and operational incidents.
• Coordinate cross-divisional responses to infrastructure hazards and public concerns.
• Ensure the effective collection and preservation of evidence for insurance, risk management, and legal processes.
• Monitor service quality, timeliness, and outcomes.
• Drive continuous improvement, promote a culture of safety, accountability, customer service, and operational excellence.
• Safeguard the City’s operational, financial, and legal interests.

Key Qualifications

• Post-secondary education in Civil Engineering, Transportation, Planning, Public Administration, Risk Management, Law Enforcement or a related discipline, or an equivalent combination of education and experience.
• Considerable experience in management leading operational, technical, inspection, investigation, claims, compliance, or road-maintenance functions in a complex public or private sector organization.
• Experience in leading, motivating, and developing teams emphasizing continuous improvement, accountability, employee engagement, and high performance.
• Experience conducting or overseeing field investigations, infrastructure inspections, evidence collection, incident documentation, compliance audits, or claims-related investigations.
• Experience with insurance, claims, risk management, or legal processes including preparation and preservation of accurate, objective, and defensible records.
• Ability to apply legislation, regulations, standards, policies, and procedures related to roads, transportation infrastructure, municipal operations, or public safety.
• Knowledge of relevant federal, provincial, and municipal legislation, regulations, by-laws, policies, standards, and operational guidelines related to transportation operations, public safety, municipal infrastructure maintenance, claims and risk management, records management, privacy, occupational health and safety, labour relations, and regulatory compliance.
• Knowledge of contract management and procurement, including developing specifications, monitoring contractors, controlling expenditures, and addressing non-compliance.
• Familiarity with managing road maintenance, winter operations, right-of-way inspections, or other transportation-related services.
• Experience developing, administering, and monitoring annual operating and capital budgets.
• Excellent analytical, problem-solving, written and verbal communication skills.
• Excellent customer-service, interpersonal, negotiation and conflict-resolution skills.
• Ability to exercise discretion, initiative, innovation, strategic thinking, and creativity in problem-solving.
• Familiarity leading organizational or operational change and implementing new processes, technologies, or service-delivery approaches.
• Experience in issues management and resolving complex or contentious matters involving competing political, community, operational and stakeholder interests.
• Ability to establish effective working relationships with employees, the public, elected officials, contractors, external agencies, and other levels of government.
• Ability to provide leadership during emergencies, severe-weather events, and other time-sensitive operational situations.
• Possession of and ability to maintain a valid Province of Ontario Class “G” Driver’s Licence, with access to a personal vehicle as required.