Transit Ops & Maintenance Manager, Claims & Investigations

City of Toronto; Toronto; On-site; CAD 126,000 - 176,000; Full time

Job summary

City of Toronto is seeking a Manager, Transportation Operations & Maintenance (Claims and Investigations) to lead city-wide road maintenance, winter operations, and risk management initiatives. The role oversees investigations, claims and enforcement activities, ensuring safe, compliant, and customer-focused service delivery across Transportation Services.

Reporting to the Director, Winter and Seasonal Services, the Manager will provide strategic and operational leadership for claims management,

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 leading, motivating, and developing teams, with emphasis on 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 the preparation and preservation of accurate, objective, and defensible records.
• Experience applying legislation, regulations, standards, policies, and procedures related to roads, transportation infrastructure, municipal operations, or public safety.
• Knowledge of, and ability to interpret and apply, 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.
• Familiarity with developing, administering, and monitoring annual operating and capital budgets.
• Excellent analytical and problem-solving skills, with the ability to assess risk, interpret evidence, determine root causes, and recommend appropriate corrective action.
• Excellent written and verbal communication skills, including experience preparing investigation reports, briefing notes, correspondence, presentations, and Committee or Council reports.
• Excellent customer-service, interpersonal, negotiation and conflict-resolution skills, with the ability to manage sensitive and contentious matters professionally.
• Ability to exercise discretion, initiative, innovation, strategic thinking, and creativity in problem-solving.
• Familiarity with leading organizational or operational change and implementing new processes, technologies, or service-delivery approaches.
• Familiarity 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.

Responsibilities

• In this leadership role, you will 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; ensure safe, efficient, compliant, and customer-focused service.
• Reporting to the Director, Winter and Seasonal Services, oversee city-wide claims management, right-of-way patrol, field investigation, inspection, and emergency response functions.
• Provide oversight of claims investigations, field operations, and infrastructure monitoring programs, establishing standards, performance measures, and risk management practices while ensuring compliance with legislative, legal, and records management requirements.
• Responsibilities include overseeing complex and high-risk claims and operational incidents, coordinating cross-divisional responses to infrastructure hazards and public concerns, ensuring 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, and safeguard the City’s interests.

Skills

Strategic leadership

Risk management

Claims investigations

Budget management

Stakeholder engagement

Contract management

Regulatory compliance

Analytical skills

Communication skills

Emergency leadership

Education

Post-secondary education in Civil Engineering or related fields

Job description

City of Toronto is seeking a Manager, Transportation Operations & Maintenance (Claims and Investigations) to lead city-wide road maintenance, winter operations, and risk management initiatives. The role oversees investigations, claims and enforcement activities, ensuring safe, compliant, and customer-focused service delivery across Transportation Services.

Reporting to the Director, Winter and Seasonal Services, the Manager will provide strategic and operational leadership for claims management,