Associate Director: Risk Management & Insurance Strategy

Associate Director: Risk Management & Insurance Strategy Join an award-winning organisation that delivers world-class workforce solutions while fostering a vibrant, collaborative, and growth-oriented work culture. At Cynet, you will work alongside passionate professionals and contribute toward building scalable business operations and strategic excellence. Position Overview We are seeking a strategic and high-impact Associate Director of Risk Management & Insurance Strategy to lead our enterprise risk portfolio. Reporting directly to the CFO, this individual will transition our insurance function from a tactical administrative process to a strategic value-driver. The Associate Director will not only oversee the day-to-day execution of renewals and compliance but will also act as a senior advisor on risk appetite, cost mitigation, and long-term insurance architecture. The ideal candidate will possess the technical rigour to manage complex US P&C programs and the strategic vision to forecast risk trends within the staffing industry, ensuring our insurance program evolves ahead of our business expansion. Strategic Leadership Responsibilities Total Cost of Risk (TCOR) Management Develop and own the TCOR framework. Analyze premiums, retained losses (deductibles), and administrative costs to provide senior leadership with a comprehensive view of risk-related spend. Risk Appetite & Retention Strategy Evaluate and recommend optimal risk retention levels. Lead the feasibility analysis for alternative risk transfer mechanisms, such as high-deductible programs or captive insurance models. Predictive Risk Advisory Partner with the Executive and Sales teams to perform Pre-Entry Risk Assessments for new business lines or geographic expansions, identifying potential coverage gaps before they impact the balance sheet. Loss Control & Mitigation Lead the Safety & Loss Control strategy. Implement proactive injury prevention and Return-to-Work programs to aggressively drive down the Experience Modifier (E-Mod) and long-term Workers’ Comp costs. Advanced Contractual Negotiation Go beyond basic COI compliance to consult on complex indemnification, “Limit of Liability,” and “Hold Harmless” clauses in Master Service Agreements (MSAs). Review, analyse, and document contracts to ensure strict insurance and risk compliance. Industry Intelligence Proactively stay abreast of the latest developments in the insurance industry, emerging risks, and regulatory changes to ensure the company’s program remains best-in-class. Tactical & Operational Excellence End-to-End Renewal Ownership Project-manage the annual renewal lifecycle for all lines (GL, E&O/Cyber, D&O, Workers’ Comp, and Umbrella), ensuring 100% on-time submission. Data Governance & WC Classification Act as the central hub for the Finance, HR, and Data teams. Meticulously ensure all employees are correctly classified for Workers' Compensation purposes and that payroll audits and exposure data are 100% accurate. Broker Accountability Manage relationships with US-based brokers, auditing their performance and ensuring aggressive market competition for renewals. Claims Management & Monitoring Provide oversight on high-value or escalated claims. Responsibilities include reporting and monitoring all liability claims and workplace incidents (Workers' Comp, General and Professional Liability, Employment Practices, etc.) and working with legal counsel to ensure favourable resolutions. Internal Training & Audit Readiness Create and maintain “Insurance Playbooks” to educate the Business and Operations teams. Maintain comprehensive records to ensure constant audit readiness for insurance and regulatory reviews. Qualifications & Skills Education Bachelor’s/Master’s degree in Finance, Risk Management, or Law. MBA preferred. Experience 10+ years of progressive experience in Corporate Risk Management or Commercial Insurance, with significant experience supporting US-based entities. Technical Knowledge Deep understanding of US P&C insurance markets, NCCI classifications, and “Claims-Made” vs. “Occurrence” policy forms. Certifications Professional designations such as ARM (Associate in Risk Management