Position SummaryThe Director of Risk Management - Transportation Sales is a strategic, client-facing leader responsible for developing and delivering risk management strategies that support the growth, retention, and profitability of the Transportation business.
Working closely with Transportation Sales leadership, producers, carrier partners, and clients, this role will provide specialized expertise in identifying, evaluating, and mitigating the complex risks associated with transportation and fleet operations. The Director will serve as a trusted advisor to clients, helping them improve their overall risk profile, reduce the frequency and severity of losses, strengthen safety and loss-control practices, and position their organizations more effectively within the insurance marketplace.
This role will also be an important component of the Transportation Sales value proposition, partnering with sales teams throughout the prospecting, client acquisition, renewal, and retention lifecycle to differentiate the organization through sophisticated risk-management capabilities.
ResponsibilitiesRisk Management Strategy & Client Advisory
- Serve as a senior risk-management advisor to transportation clients and prospects, providing practical and strategic guidance regarding fleet safety, loss prevention, claims trends, regulatory exposures, and overall risk quality.
- Conduct comprehensive assessments of client operations, loss experience, safety programs, policies, procedures, and risk-management practices.
- Develop customized risk-mitigation strategies and action plans based on each client's operations, exposures, loss drivers, and business objectives.
- Analyze loss data and operational trends to identify root causes, emerging risks, and opportunities to reduce claim frequency and severity.
- Provide recommendations related to driver management, fleet safety, accident prevention, regulatory compliance, vehicle maintenance, and other transportation-specific risk exposures.
- Establish appropriate metrics and benchmarks to measure the effectiveness of client risk-management initiatives and demonstrate measurable improvement over time.
Sales & Business Development
- Partner closely with Transportation Sales leadership and producers to integrate risk-management capabilities into the overall sales strategy and client value proposition.
- Participate in prospect meetings, presentations, finalist meetings, and other business-development activities as the transportation risk-management subject-matter expert.
- Assess prospective clients' risk profiles and identify opportunities to demonstrate differentiated risk-management capabilities during the sales process.
- Translate complex risk-management concepts into clear, compelling business solutions for clients and prospects.
- Support producers in developing strategies for complex or challenging transportation risks.
- Contribute to client retention by demonstrating ongoing value beyond insurance placement and helping clients achieve measurable improvements in their risk profiles.
Carrier & Marketplace Partnership
- Partner with underwriting, carrier, loss-control, claims, and safety resources to develop coordinated strategies for clients and prospects.
- Help clients prepare for carrier loss-control reviews, underwriting meetings, and renewal discussions.
- Identify and address risk-quality issues that may negatively affect coverage availability, pricing, terms, or carrier appetite.
- Support producers and clients in communicating improvements in risk quality and loss performance to insurance markets.
- Maintain strong knowledge of carrier expectations, underwriting trends, and emerging risk-management requirements within the transportation insurance marketplace.
Transportation Safety & Loss Control
- Provide subject-matter expertise regarding commercial auto and transportation exposures, including fleet operations, driver safety, vehicle maintenance, cargo, workers' compensation, and related operational risks.
- Evaluate driver qualification and selection practices, onboarding and training programs, motor vehicle record monitoring, accident review processes, and corrective-action programs.
- Advise clients regarding Department of Transportation (DOT) and Federal Motor Carrier Safety Administration (FMCSA) requirements and industry best practices.
- Analyze relevant safety and compliance data, including CSA performance and other available fleet and driver metrics, to identify areas of risk and opportunity.
- Advise clients regarding emerging transportation risks and technologies, including telematics, cameras, driver-monitoring systems, advanced driver-assistance technologies, and other fleet-safety solutions.
- Collaborate with internal and external resources to deliver training, safety programs, and loss-control solutions.
Claims & Loss Trend Analysis
- Partner with claims professionals and clients to analyze significant losses, recurring claim patterns, and emerging loss trends.
- Facilitate or support large-loss and claims-review meetings, identifying actionable risk-management recommendations.
- Use claims and loss data to develop targeted prevention strategies and measure improvement.
- Help clients establish effective accident investigation, post-accident response, and corrective-action processes.
- Leadership & Practice Development
- Help develop and continuously enhance the Transportation business's risk-management strategy, service model, tools, resources, and client deliverables.
- Establish consistent standards and best practices for transportation risk-management services.
- Develop scalable resources, benchmarking tools, presentations, and client-facing materials that can be leveraged across the Transportation Sales organization.
- Educate producers and other internal stakeholders on transportation risk trends, loss-control strategies, and opportunities to incorporate risk management into the sales process.
- Monitor emerging industry trends, technologies, regulations, litigation trends, and loss drivers affecting transportation clients.
- Represent the organization as a transportation risk-management thought leader with clients, prospects, carriers, and industry partners.
Requirements- Deep knowledge of commercial transportation and fleet exposures, particularly commercial auto liability and related casualty risks.
- Strong understanding of DOT/FMCSA regulations, fleet-safety practices, driver qualification standards, and transportation loss-control methodologies.
- Demonstrated ability to analyze claims, loss, safety, and operational data and translate findings into actionable recommendations.
- Strong executive presence with the ability to build credibility with business owners, C-suite executives, safety leaders, operations leaders, producers, underwriters, and carrier partners.
- Excellent presentation, communication, facilitation, and relationship-management skills.
- Ability to balance technical risk-management expertise with a commercial, client-focused mindset.
- Ability to travel as required to support clients, prospects, sales teams, and business-development activities.
Education and Experience- Bachelor's degree in Risk Management, Insurance, Safety, Transportation, Business, or a related discipline preferred.
- Typically 8+ years of progressive experience in transportation risk management, commercial insurance, loss control, fleet safety, transportation safety, or a related discipline.
- Experience working directly with transportation companies, insurance carriers, brokers, or transportation-focused risk-management organizations strongly preferred.
- Experience supporting sales, business development, or client-retention activities in a consultative environment preferred.
Candidates should be comfortable with an on-site presence to support collaboration, team leadership, and cross-functional partnership. 
