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The Director of Risk Management provides strategic leadership and oversight for Gulf Winds International’s enterprise risk, claims, insurance, compliance, and loss prevention programs. This role partners with executive leadership, Operations, Safety, Finance, Human Resources, external counsel, insurance brokers, carriers, third‑party administrators, and other business partners to identify, assess, mitigate, and manage risk across the organization. The Director of Risk Management will lead efforts related to transportation and logistics claims, insurance renewals, litigation management, mediation, incident response, risk assessment, contractual risk review, claims cost containment, and risk‑related compliance considerations. This role is responsible for strengthening risk controls, supporting FMCSA/DOT and OSHA‑aligned compliance efforts, protecting company assets, and driving proactive strategies that reduce financial, operational, reputational, regulatory, and legal exposure across trucking, transportation, warehouse, and logistics operations.

• Develop and maintain strong relationships with insurance brokers, carriers, adjusters, attorneys, TPAs, vendors, and operational leaders to ensure effective communication, timely claim progression, and disciplined risk management practices.
• Manage litigated claims and legal matters in partnership with internal stakeholders, outside counsel, insurance carriers, brokers, and third‑party administrators; support case strategy, discovery coordination, settlement evaluation, mediation preparation, and resolution recommendations.
• Oversee the management of complex claims, including auto liability, cargo, physical damage, property damage, bodily injury, workers’ compensation, warehouse, and third‑party claims; ensure claims are investigated, documented, evaluated, and resolved in the best interest of the company.
• Lead annual insurance renewal processes, including exposure data collection, policy review, application support, loss run analysis, broker/carrier communication, premium and deductible review, and recommendations related to coverage structure and risk financing.
• Monitor claim trends, loss experience, insurance costs, open reserves, litigation exposure, and key risk indicators; prepare recurring reports and executive‑level updates with actionable recommendations for improvement.
• Support incident response protocols, including evidence preservation, accident investigation, FMCSA/DOT or OSHA‑related reporting considerations, post‑incident communication, and coordination with counsel or insurance partners when litigation or significant exposure is anticipated.
• Partner with Safety and Operations leadership to evaluate accidents, incidents, driver‑related events, facility exposures, OSHA‑recordable trends, DOT‑reportable events, and process gaps; recommend corrective actions, training, documentation improvements, and controls to prevent recurrence.
• Lead, coach, and develop risk, claims, and/or safety‑related team members as assigned; create a high‑performance environment grounded in accountability, collaboration, timely follow‑through, and sound judgment.
• Provide strategic leadership for the development, implementation, and continuous improvement of enterprise risk management programs, policies, procedures, and controls that support Gulf Winds International’s business objectives, operational performance, and financial protection.
• This description is not an exhaustive or comprehensive list of all job responsibilities, tasks, and duties. Other duties and responsibilities may be assigned, and the scope of the job may change as necessitated by business demands.
• Review contracts, customer requirements, certificates of insurance, indemnity provisions, and other risk‑related documentation in partnership with legal, finance, sales, and operations teams to identify and communicate potential exposure.
• Lead risk assessment and loss prevention initiatives across trucking, transportation, warehouse, and logistics operations; identify exposure trends and recommend strategies to reduce claim frequency, claim severity, litigation risk, regulatory exposure, and preventable losses.
  • Partner with Safety and Operations to support FMCSA/DOT‑related risk controls, including exposure areas such as driver qualification, hours of service, vehicle maintenance, accident documentation, post‑incident review, and transportation safety compliance practices.

• Bachelor’s degree in Risk Management, Business, Finance, Legal Studies, Insurance, Supply Chain, Transportation, or a related field required; advanced degree, insurance designation, or legal background preferred.
• Minimum of 8–10 years of progressive experience in risk management, claims management, insurance, litigation support, loss prevention, or related functions, preferably within trucking, transportation, logistics, intermodal, or fleet‑based operations.
• Strong working knowledge of transportation‑related claims, including auto liability, cargo, physical damage, property damage, bodily injury, workers’ compensation, and third‑party claims.
• Working knowledge of FMCSA/DOT regulations and transportation safety compliance concepts, including driver qualification, hours of service, vehicle maintenance, accident reporting/documentation, CSA/SMS exposure, and related fleet risk controls preferred.
• Working knowledge of OSHA requirements and warehouse/facility safety exposure areas, including injury and illness recordkeeping, material handling, powered industrial trucks, walking‑working surfaces, and workplace injury prevention preferred.
• Experience managing litigated claims, working with outside counsel, preparing for mediation, evaluating settlements, and supporting legal strategy strongly preferred.
• Experience supporting commercial insurance renewals, policy review, loss run analysis, broker/carrier relationships, coverage evaluation, and risk financing decisions preferred.
• Ability to analyze and rate risks, exposures, loss expectancies, reserves, claim trends, and operational vulnerabilities, and effectively associate these with practical risk management alternatives.
• Strong analytical, investigative, negotiation, mediation, documentation, and problem‑solving skills.
• Proficiency with Microsoft Excel, PowerPoint, Word, claims/risk management systems, reporting tools, and web‑based insurance or claims platforms.