Director Insurance Risk Jobs in Toronto, ON (NOW HIRING)

Job ID: 66849
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
Salary Range: $126,000.00 - $176,140.00
Shift Information: Monday to Friday, 35 hours per week
Affiliation: Non-Union
Number of Positions Open: 1
Posting Period: 01-Sep-2026 to 22-Sep-2026 

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:
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; and ensure safe, efficient, compliant, and customer-focused service.

Reporting to the Director, Winter and Seasonal Services, the Manager, Claims and Investigations will provide strategic and operational leadership for the Division's city-wide claims management, right-of-way patrol, field investigation, inspection, and emergency response functions. The role provides 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, and monitoring service quality, timeliness, and outcomes. The Manager drives continuous improvement, promotes a culture of safety, accountability, customer service, and operational excellence, and safeguards the City's operational, financial, and legal interests.

Key Qualifications:

1. 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.
2. Considerable experience in management, leading operational, technical, inspection, investigation, claims, compliance, or road-maintenance functions in a complex public or private sector organization.
3. Considerable experience leading, motivating, and developing teams, with an emphasis on continuous improvement, accountability, employee engagement, and high performance.
4. Considerable experience conducting or overseeing field investigations, infrastructure inspections, evidence collection, incident documentation, compliance audits, or claims-related investigations.
5. Experience with insurance, claims, risk management, or legal processes, including the preparation and preservation of accurate, objective, and defensible records.
6. Experience applying legislation, regulations, standards, policies, and procedures related to roads, transportation infrastructure, municipal operations, or public safety.
7. 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.
8. Knowledge of contract management and procurement, including developing specifications, monitoring contractors, controlling expenditures, and addressing non-compliance.
9. Familiarity with managing road maintenance, winter operations, right-of-way inspections, or other transportation-related services.
10. Familiarity with developing, administering, and monitoring annual operating and capital budgets.
11. Excellent analytical and problem-solving skills, with the ability to assess risk, interpret evidence, determine root causes, and recommend appropriate corrective action.
12. Excellent written and verbal communication skills, including experience preparing investigation reports, briefing notes, correspondence, presentations, and Committee or Council reports.
13. Excellent customer-service, interpersonal, negotiation and conflict-resolution skills, with the ability to manage sensitive and contentious matters professionally.
14. Ability to exercise discretion, initiative, innovation, strategic thinking, and creativity in problem-solving.
15. Familiarity with leading organizational or operational change and implementing new processes, technologies, or service-delivery approaches.
16. Familiarity in issues management and resolving complex or contentious matters involving competing political, community, operational and stakeholder interests.
17. Ability to establish effective working relationships with employees, the public, elected officials, contractors, external agencies, and other levels of government.
18. Ability to provide leadership during emergencies, severe-weather events, and other time-sensitive operational situations.
19. Possession of and ability to maintain a valid Province of Ontario Class "G" Driver's Licence, with access to a personal vehicle as required.

Note to Internal Full-Time and Part-Time City of Toronto Employees
City of Toronto employees must apply to full-time or part-time employment opportunities posted on the City's Internal Job Posting Portal.

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.