Vice President of Insurance and Claims

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 companys 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 companys 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

• Bachelors 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.

Required Experience:

Exec