- Experience
- 3+ years
- Education
- Bachelor
- Source
- Fountain
Description
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 WeDriveU’s 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
Preferred Qualifications
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.
We Offer
Physical Health
Exceptional Medical, Dental, Vision, and Life Insurance benefits
Financial Health
Competitive compensation packages
401(k) with 4% employer match
Financial Wellness Tool
Commuter Benefits
Emotional Health
Employee Assistance Program (EAP)
Unlimited PTO
Paid holidays
Pet & Legal Insurance
Personal Development
On-the-job training and skills development
Internal transfer opportunities for career growth
*Benefits vary by position and location
WeDriveU is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment free of discrimination or harassment where thoughts and ideas of all employees are appreciated and respected. We value excellence and recognize that by respecting the diverse backgrounds, skills, and perspectives of our workforce, we will sustain a competitive advantage and remain an employer of choice. We also see diversity as more than policies; it is imperative for enabling us to attract, retain and develop the best talent available.
