Director of Risk Management - Transportation Sales

About Acrisure

A global fintech leader, Acrisure empowers millions of ambitious businesses and individuals with the right solutions to grow boldly forward. Bringing cutting-edge technology and top-tier human support together, we connect clients with customized solutions across a range of insurance, reinsurance, payroll, benefits, cybersecurity, mortgage services – and more. 

In the last twelve years, Acrisure has grown in revenue from $38 million to almost $5 billion and employs over 19,000 colleagues in more than 20 countries. Acrisure was built on entrepreneurial spirit. Prioritizing leadership, accountability, and collaboration, we equip our teams to work at the highest levels possible.

Position Summary

The 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.

Responsibilities

Risk 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.

Why Join Us:

At Acrisure, we’re building more than a business, we’re building a community where people can grow, thrive, and make an impact. Our benefits are designed to support every dimension of your life, from your health and finances to your family and future.

Making a lasting impact on the communities it serves, Acrisure has pledged more than $22 million through its partnerships with Corewell Health Helen DeVos Children's Hospital in Grand Rapids, Michigan, UPMC Children's Hospital in Pittsburgh, Pennsylvania and Blythedale Children's Hospital in Valhalla, New York.

Employee Benefits

We also offer our employees a comprehensive suite of benefits and perks, including:

• Physical Wellness: Comprehensive medical insurance, dental insurance, and vision insurance; life and disability insurance; fertility benefits; wellness resources; and paid sick time.

• Mental Wellness: Generous paid time off and holidays; Employee Assistance Program (EAP); and a complimentary Calm app subscription.

• Financial Wellness: Immediate vesting in a 401(k) plan; Health Savings Account (HSA) and Flexible Spending Account (FSA) options; commuter benefits; and employee discount programs.

• Family Care: Paid maternity leave and paid paternity leave (including for adoptive parents); legal plan options; and pet insurance coverage.

• … and so much more!

This list is not exhaustive of all available benefits. Eligibility and waiting periods may apply to certain offerings. Benefits may vary based on subsidiary entity and geographic location.

Acrisure is an Equal Opportunity Employer. We consider qualified applicants without regard to race, color, religion, sex, national origin, disability, or protected veteran status. Applicants may request reasonable accommodation by contacting leaves@acrisure.com.

Final candidates will be required to complete post-offer verification processes related to the role and in accordance with applicable laws.

California Residents: Learn more about our privacy practices for applicants by visiting the Acrisure California Applicant Privacy Policy.

Recruitment Fraud: Please visit here to learn more about our Recruitment Fraud Notice.

Welcome, your new opportunity awaits you.