Director Insurance & Risk Management Jobs in Toronto, ON

Job ID: 65924

Job Category: Finance, Accounting & Purchasing

Division & Section: Chief Financial Officer's Office, Insurance & Risk Management

Work Location: CITY HALL, 100 Queen St W, Toronto, M5H 2N1

Job Type & Duration: Full-time, Permanent Vacancy

Salary Range: $105,241 - $146,191, PSG #TM1817, Wage Grade PTM3 

Shift Information: Monday to Friday, 35 hours per week 

Affiliation: Non-Union

Number of Positions Open: 1

Posting Period: 24-AUG-2026 to 07-SEP-2026

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.

Reporting to the Director, Insurance & Risk Management, and leading a team of unionized professionals, the Supervisor, Insurance & Risk Management provides leadership and oversight for insurance, risk management, and related claims administration activities.

This role is responsible for 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, 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.

The Impact You'll Make

As Supervisor, Insurance & Risk Management, you will lead a team responsible for delivering insurance and risk management services across a large and complex organization. You will provide day-to-day leadership, overseeing workload distribution, setting priorities, monitoring performance, and fostering a positive, productive, and collaborative team environment.

You will oversee 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. Acting as a key point of escalation, you will help ensure that complex and urgent insurance and risk management matters are addressed effectively and in a timely manner.

Working closely with City divisions, agencies, corporations, insurers, brokers, and legal counsel, you will supervise the annual corporate insurance renewal process, review policy quotations and coverage terms, and provide recommendations to support effective insurance protection and risk transfer strategies.

You will oversee insurance-related compliance activities, including insurance certificate administration, and regulatory requirements related to regulated objects requiring jurisdictional inspections. You will also support procurement activities, contract reviews, policy development, and continuous improvement initiatives that enhance operational effectiveness and risk management practices.

You will oversee the procurement of service providers, technical solutions and professional services through RFPs and supervise the lead staff in the evaluation, selection and recommendation through report preparation to Bid Committee, Standing Committee and City Council as required.

You will manage vendor service contracts to ensure compliance with contract requirements and service level standards.

You will conduct research and monitor industry, legislative, regulatory, and municipal peers to support policy recommendations, program improvements, and evolving risk management needs. You will also facilitate presentations, seminars, and training initiatives that promote awareness of insurance, risk management, loss control, and emerging trends across the organization.

The primary focus of this role is ensuring that insurance and risk management programs, processes, and controls support the organization's overall risk management objectives.

As a member of the management team, you will provide strategic and operational advice, contribute to service improvements, provide input into and administer assigned budgets, support financial accountability, and act on behalf of the Director when required.

Key Qualifications

• 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.

Why You Will Love Working at The City:

1. We recognize the need for flexibility and offer a hybrid working environment that will provide you with an appropriate work-life balance required to thrive in today's fast paced world.
2. A strong benefits package which includes competitive salaries, vacation, and other unique offerings.
3. We offer an excellent defined benefit pension plan bringing added value to our overall compensation package through OMERS.
4. We support ongoing learning and development and offer educational opportunities with tuition subsidies.
5. Opportunities to join and take an active role with City's Communities of Inclusions comprised of employees who share a common identity, lived experience and/or set of interest and support each other's professional development, sense of belonging and promote a culture of inclusion.

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.