Kevin Mealey

Director of Cross-Border Sales
Swan Insurance

Kevin Mealey

Kevin Mealey leads all cross-border operations at S.W.A.N. Insurance, where he and his team specialize exclusively in providing U.S. insurance programs for Mexico-based carriers. His focus is on aligning insurance coverage with real-world fleet operations - legally, administratively, and operationally.

Kevin supports mid- to large-sized fleets, particularly those operating with B-1 drivers, multiple terminals, and complex logistics demands. He works directly with compliance teams, operations leads, dispatchers, and ownership to ensure the insurance program integrates with internal systems, rather than creating additional friction.

Under his direction, S.W.A.N. Insurance maintains a lean, specialized portfolio that allows for high-touch service, consistent communication, and direct access to the people managing risk inside each client's operation. His approach is structured, proactive, and fully informed by the realities of cross-border fleet management.

About Kevin

Areas of Expertise

  • U.S. Risk Management for Cross-Border Fleets

Designing insurance programs to reflect real operational exposure, including liability, cargo, and excess coverage structured for cross-border hauling and B-1 driver fleets.

  • Compliance Alignment and Integration

Utilizing Swan’s proprietary ARM platform to manage filings, driver and vehicle updates, certificates, and internal audit support for safety and compliance teams.

  • Claims Management and Coordination

Managing claims internally with response initiated within 24 hours, supported by bilingual service and ongoing communication with client-side safety leads.

  • Operational Support Beyond the Policy

Supporting endorsement tracking, contractual insurance reviews, and compliance documentation throughout the policy year, not just at renewal.

  • Cross-Department Collaboration

Providing structured support that integrates with administrative, dispatch, and safety teams to reduce downtime, improve accuracy, and align operations.

  • Scalable Planning and Strategic Risk Review

Assisting clients in long-term planning, including transitions into captive structures or market shifts based on fleet size and future goals.

Why Work with Kevin Mealey?

Kevin is not a retail agent. He works exclusively with established cross-border fleets and runs a dedicated service team structured around consistency, responsiveness, and subject matter depth.

  • Trusted by growing and established cross-border carriers operating into the U.S.
  • Operates with a small, focused account base to ensure meaningful oversight and continuity
  • Maintains structured client reviews, monthly audits, and tracked endorsements through the ARM system
  • Deep experience managing B-1 driver programs, regulatory filings, and U.S. broker contract requirements
  • Known for building programs that reduce administrative burden while improving compliance performance
  • Fluent in operational risk planning and internal alignment for mid- to large-scale fleets

S.W.A.N. stands for Sleep Well At Night. For Kevin and his team, that means risk is addressed before it becomes a problem. With clear processes, dedicated support, and full alignment with your internal departments, nothing is left to chance.

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