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About WeDriveUWeDriveU is a premier provider of mobility solutions, specializing in shuttle and transit services that connect communities, campuses, and workplaces across the United States. As a business unit of the global mobility provider Mobico Group, WeDriveU is committed to delivering safe, sustainable, and innovative transportation options that enhance accessibility and reduce environmental impact.

Position SummaryThe VP of Insurance and Claims leads WeDriveUs enterprise-wide strategy to protect people, property, and brand reputation. This role is responsible for overseeing all aspects of corporate insurance programs, claims management, and risk mitigation strategies while also holding oversight of compliance functions critical to operational and legal integrity. This executive leader works cross-functionally with Safety, Legal, HR, and Operations to ensure alignment, reduce exposure, and drive a strong culture of accountability and compliance.

Key Responsibilities

Insurance Program

• Design, negotiate, and manage the company's overall insurance program, including auto liability, general liability, workers' compensation, umbrella/excess, property, and other specialty coverage lines.

• Lead annual renewal strategy, marketing, and placement in partnership with brokers and underwriters; benchmark coverage, pricing, and retention structures against industry peers.

• Own the total cost of risk (TCOR) analysis and reporting and identify strategies to reduce it year over year.

• Review insurance and indemnification requirements in customer, vendor, and subcontractor contracts, and advise business development and operations on coverage adequacy and gaps.

Claims Management

• Oversee the full claims lifecycle for auto, general liability, workers' compensation, and property claims, including intake, investigation, reserving, litigation management, and resolution.

• Oversee teams managing third-party administrators (TPAs), adjusters, and defense counsel to ensure timely, cost-effective claims handling and appropriate reserve accuracy.

• Partner with the General Counsel and outside counsel on claims that escalate to litigation, coordinating strategy while maintaining ownership of the claims relationship and financial exposure.

• Establish protocols for tracking claims trends by location, route, and driver to identify systemic risk drivers and inform loss prevention priorities and for subrogation efforts to recover costs where appropriate.

Risk Assessment & Loss Control

• Conduct enterprise-wide risk assessments across operations, fleet, facilities, and new business lines; identify emerging risks and recommend mitigation strategies.

• Partner with Safety on programs that directly influence loss experience and insurability.

• Support due diligence and risk evaluation for new contracts, new markets, mergers, acquisitions, and new service lines.

• Monitor incident trends and regulatory developments (Federal, state, OSHA, FTA, FMCSA, DOT, Public Utilities Commissions) that affect the company's risk profile, complianc, and insurability.

Leadership & Cross-Functional Partnership

• Build, lead, and develop the risk management and claims team as the function scales.

• Serve as the primary point of contact for brokers, carriers, TPAs, and risk consultants.

• Present risk management strategy, loss trends, TCOR, and program performance to executive leadership and, as needed, the Board.

• Partner with Finance on risk-related budgeting, reserve accounting, actuarial analysis, and reporting.

• Maintain awareness of industry trends, market conditions, and regulatory changes affecting the transportation risk landscape.

Qualifications

• Bachelor's degree required; advanced degree or professional designation (ARM, CPCU, CRIS, or similar) strongly preferred.

• 10+ years of progressive risk management experience, including insurance program management and claims oversight, with at least 3+ years in a leadership role.

• Demonstrated experience managing commercial insurance placements across multiple coverage lines, including commercial auto, general liability, workers' compensation, and umbrella/excess insurance.

• Experience managing self-insured or high-deductible programs and captive/fronting insurance structures.

• Strong insurance procurement, renewal, broker, and carrier management experience.

• Strong understanding of claims oversight and total cost of risk, reserving methodology, and risk finance reporting.

• Excellent negotiation, analytical, and communication skills, with the ability to translate complex risk concepts into practical business guidance.

• Strong analytical skills with experience using claims and actuarial data to drive decisions - strong financial management of insurance and claims program

• Strong reporting process - both to the WeDriveU executive team and into Group

• Bilingual proficiency (English/Spanish) strongly preferred

• Expertise in transportation, fleet, transit, or logistics risk.

• Familiarity with OSHA, DOT, FMLA, and ADA requirements as they relate to risk and insurability.

• Knowledge of government contracting and transportation regulatory risks (FTA, FMCSA, state regulations).

• Experience with contracting risk requirements, including insurance and indemnification provisions in contracts.

• Experience with claims and risk information systems (RMIS) and data-driven loss analysis.