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About the Role

The City of Toronto is seeking a Supervisor, Insurance & Risk Management to lead a team responsible for delivering insurance and risk management services. This role involves supervising the delivery of insurance and risk management services, supporting the City's corporate insurance program, coordinating annual insurance renewals, and advancing loss control and risk mitigation initiatives. The successful candidate will combine strong people leadership skills with sound insurance and risk management knowledge to support organizational priorities and deliver excellent client service.

Responsibilities

Supervising the delivery of insurance and risk management services.
Supporting the City's corporate insurance program.
Coordinating annual insurance renewals.
Providing expertise on insurance and contractual risk transfer requirements.
Advancing loss control and risk mitigation initiatives.
Providing day-to-day leadership, overseeing workload distribution, setting priorities, monitoring performance, and fostering a positive, productive, and collaborative team environment.
Overseeing the development and implementation of risk management, insurance, and loss control initiatives.
Providing specialized guidance to internal stakeholders on insurance programs, contractual insurance requirements, certificates of insurance, risk financing and contractual risk transfer techniques, liability loss control, and insurance compliance matters.
Ensuring that complex and urgent insurance and risk management matters are addressed effectively and in a timely manner.
Supervising the annual corporate insurance renewal process.
Reviewing policy quotations and coverage terms.
Providing recommendations to support effective insurance protection and risk transfer strategies.
Overseeing insurance-related compliance activities, including insurance certificate administration, and regulatory requirements related to regulated objects requiring jurisdictional inspections.
Supporting procurement activities, contract reviews, policy development, and continuous improvement initiatives that enhance operational effectiveness and risk management practices.
Overseeing the procurement of service providers, technical solutions and professional services through RFPs.
Supervising the lead staff in the evaluation, selection and recommendation through report preparation to Bid Committee, Standing Committee and City Council as required.
Managing vendor service contracts to ensure compliance with contract requirements and service level standards.
Conducting research and monitoring industry, legislative, regulatory, and municipal peers to support policy recommendations, program improvements, and evolving risk management needs.
Facilitating presentations, seminars, and training initiatives that promote awareness of insurance, risk management, loss control, and emerging trends across the organization.
Ensuring that insurance and risk management programs, processes, and controls support the organization's overall risk management objectives.
Providing strategic and operational advice as a member of the management team.
Contributing to service improvements.
Providing input into and administering assigned budgets.
Supporting financial accountability.
Acting on behalf of the Director when required.

Requirements

Post-secondary education in Insurance, Risk Management, Business Administration, Public Administration, or a related discipline, or an equivalent combination of education and experience.
Professional designations such as CIP or CRM are preferred.
Considerable experience leading and developing staff, including direct people management responsibilities.
Considerable experience working in a unionized environment, including supervising staff in a hybrid work setting.
Considerable experience in insurance, risk management, loss control, or a related field.
Considerable experience administering corporate insurance programs, including policy review, insurance renewals, and coverage analysis.
Strong knowledge of insurance principles, risk financing, contractual risk transfer, and insurance compliance requirements.
Demonstrated experience reviewing and interpreting insurance provisions within contracts, leases, procurement documents, or construction-related agreements.
Strong ability to build relationships and provide advice to a broad range of internal and external stakeholders.
Experience developing, implementing, and improving policies, procedures, and operational controls.
Strong analytical, problem-solving, and decision-making skills with the ability to manage complex issues and competing priorities.
Excellent communication and presentation skills, including the ability to prepare reports, recommendations, briefing materials, and deliver presentations to diverse audiences.
Advanced proficiency with Microsoft Office applications, particularly Excel.
Experience with insurance and risk management systems is considered an asset.

Skills

People leadership
Insurance knowledge
Risk management knowledge
Relationship building
Stakeholder advisory
Policy development
Procedure development
Operational control improvement
Analytical skills
Problem-solving skills
Decision-making skills
Complex issue management
Priority management
Communication skills
Presentation skills
Report preparation
Microsoft Office proficiency
Excel proficiency

Location

CITY HALL, 100 Queen St W, Toronto, M5H 2N1

Work Type

Full-time
Permanent
Hybrid working environment

Experience Level

Considerable experience leading and developing staff
Considerable experience working in a unionized environment
Considerable experience in insurance, risk management, loss control, or a related field
Considerable experience administering corporate insurance programs

Education Level

Post-secondary education in Insurance, Risk Management, Business Administration, Public Administration, or a related discipline
Equivalent combination of education and experience
Professional designations such as CIP or CRM are preferred

Salary/Compensations

$105,241 - $146,191

Benefits

Competitive salaries
Vacation
Other unique offerings
Excellent defined benefit pension plan (OMERS)
Ongoing learning and development opportunities
Tuition subsidies

About the Company

Recognized as one of Greater Toronto’s Top Employers for 2026, the City of Toronto promotes professional development and is committed to providing opportunities to lead, learn and grow.
We value integrity, reliability, and fairness, and we embrace the diversity of the people we work with and serve.
As part of the Chief Financial Officer's Office, Insurance & Risk Management (IRM) plays an important role in supporting the City through its Insurance & Risk Management and Claims Management functions.
The division provides strategic advice, risk management expertise, and insurance services that help safeguard City operations and support informed decision-making across the organization.

Equal Opportunity

The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve.
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.