Vice President, Insurance and Risk – WP Osborne Executive Search Inc.

Starlight Investments, in conjunction with WP Osborne Executive Search, is seeking a Vice President, Insurance and Risk to join their Legal team.

Vice President, Insurance and Risk

Reporting to the EVP, General Counsel, the Vice President, Insurance and Risk is responsible for overseeing Starlight’s risk management and insurance programs across all business lines and geographies, including Canada, the United States and the United Kingdom.

The Vice President will lead the organization’s insurance portfolio, claims management framework and risk mitigation strategies, while partnering cross-functionally to support operational effectiveness, business continuity and long-term organizational objectives. The role is also responsible for managing key external relationships, overseeing the Insurance and Risk team and driving continuous improvement across reporting, analytics, systems and governance practices.

Duties and Responsibilities:

Leadership & Risk Management

• Lead, mentor and develop the Insurance and Risk team, fostering a high-performance, collaborative and service-oriented function;
• Drive continuous improvement across claims management, insurance administration, reporting, risk mitigation and stakeholder service delivery;
• Develop, maintain and continuously enhance risk management frameworks, policies, procedures and governance practices across all business lines and geographies;
• Provide risk management guidance, communication and training to various internal stakeholders and operating groups;
• Partner cross-functionally with Investments, Asset Management, Construction, Development, Operations, Finance, Legal and third-party property managers to identify emerging risks and implement mitigation strategies;
• Support business continuity, operational resiliency and crisis response initiatives in partnership with key internal stakeholders.

Insurance & Claims Oversight

• Oversee all insurance programs, including Property, Casualty, Boiler & Machinery, Automobile, Cyber, Directors & Officers and other related coverages;
• Continuously review policy language, coverage structure, deductibles, limits and market benchmarks and recommend adjustments as appropriate;
• Support brokers in the marketing, placement and renewal of insurance programs;
• Oversee the investigation, management and resolution of liability, property and construction-related claims;
• Supervise claims reporting, reserve monitoring, trend analysis and periodic reporting;
• Maintain strong working relationships with brokers, insurers, adjusters, consultants and external legal counsel;
• Monitor emerging risks and market trends, including cyber, environmental, regulatory, operational and construction-related exposures, and recommend appropriate mitigation and insurance strategies;
• Participate in broker evaluations and tender processes, where appropriate.

Strategic & Operational Support

• Support acquisitions, dispositions, refinancing and development transactions by overseeing insurance diligence, lender requirements, coverage placement and risk analysis;
• Provide strategic guidance and reporting to executive leadership regarding risk trends, claims activity, market conditions, coverage strategy and total cost of risk;
• Identify opportunities to improve operational efficiencies, reduce claims frequency and severity, and strengthen overall property performance and risk controls;
• Participate in industry and professional groups as an active representative of the organization.

Reporting & Analytics

• Oversee risk management analytics, reporting and RMIS optimization to support data-driven decision-making and operational efficiencies;
• Maintain accurate Statements of Values, insured asset schedules, automobile and equipment data and related insurance documentation;
• Deliver periodic reporting and analysis regarding claims activity, insurance performance and operational risk trends.

Qualifications

The successful candidate will possess a University Degree, College Diploma or equivalent with a minimum of 10 years of leadership experience in a risk management and/or commercial insurance position; a strong operational mindset with the ability to balance strategic leadership and hands-on execution; experience overseeing large-scale, multi-jurisdictional insurance programs and complex claims environments; strong analytical, negotiation, communication and stakeholder management skills; and the ability to influence and communicate effectively across all levels of the organization. A professional designation in Canadian Risk Management (CRM) or Certificate Insurance Professional (CIP) is considered an asset.

AI is not used to screen candidates for this role.

The compensation structure is comprised of a base salary that is market competitive and based on factors such as experience, education, designations, and skillset. It also includes a discretionary annual performance bonus tied to weighted performance targets and company performance, and company medical/dental benefits, healthcare spending accounts, a tiered employer matching group retirement savings plan and parking/Presto allowance. Other benefits include maternity top-up, investment opportunities in the company’s funds, summer office hours, annual company-wide volunteer day and many more.