Join a rapidly growing company revolutionizing the transportation industry! Cargomatic is the #1 technology platform and digital marketplace for powering world-class, local trucking. Local trucking is the lifeblood of every regional economy, and yet this $82 billion industry still relies heavily on phone calls and fax machines. We are using technology to solve complex, real-world problems every day, and giving full transparency to the shipping process.

Cargomatic is transforming the way goods move around metropolitan areas by seamlessly connecting shippers with more than 35,000 professional drivers. It facilitates several thousand shipments per day and cuts shipping-related carbon emissions by eliminating empty miles. We are solving complex, real-world problems for the industry and giving full transparency to the shipping process.

Cargomatic was named to the list of Built In Best Places to Work for 2023, 2024, & 2025 which recognizes the benefits we offer, our people-first culture and commitment to supporting our employees’ success, growth and well-being.

Our approach enables our employees – at all levels, and in every role – to thrive in an environment of intellectual curiosity, where people are passionate about what they do and support each other to get the job done. Visit www.cargomatic.com to learn more.

Position Summary:

Cargomatic is seeking an Insurance & Claims Manager to own and oversee our insurance and claims lifecycle. This individual will manage claims across cargo, liability, property, and workers' compensation, and serve as the primary point of contact with insurers, brokers, and legal partners. This role also ensures policy compliance across our growing national footprint, manages certificates of insurance, and supports renewal applications and risk mitigation strategies. Ideal candidates have a strong background in insurance and claims within the transportation or logistics space, with a hands-on, proactive approach to managing risk.

What You’ll Do:

Lead the end-to-end management of all insurance claims, including:

Cargo loss and damage
Property damage (company and third-party)
Auto and general liability
Workers’ compensation and personal injury

Serve as the primary liaison with carriers, brokers, adjusters, legal counsel, and internal teams during investigations and settlements.
Oversee the preparation and processing of Certificates of Insurance (COIs) for customers, vendors, and contractors.
Support company-wide compliance with federal, state, and local insurance regulations (e.g., FMCSA, DOT).
Coordinate with Safety, Operations, and Legal to ensure accurate and timely incident reporting.
Own the annual insurance renewal process, including data collection, application submission, and policy review.
Analyze loss trends and collaborate cross-functionally to develop and implement risk mitigation strategies.
Maintain organized claims records and tracking systems; monitor claim outcomes and financial exposure.
Audit vendor and contractor insurance compliance to ensure appropriate coverage is maintained.
Assist with litigation support and discovery for coverage disputes or related legal actions.

What You Bring:

3–5+ years of insurance and claims experience, preferably in trucking, logistics, or intermodal transportation.
Solid understanding of transportation insurance policies: cargo, auto liability, general liability, workers’ comp.
Working knowledge of COI management, risk transfer practices, and claim resolution processes.
Familiarity with insurance claims systems or TMS platforms (e.g., RMIS, Origami, or equivalent).
Strong communication and negotiation skills; ability to work across departments and external partners.
Highly organized with an eye for detail and a commitment to compliance and process improvement.

Preferred Qualifications:

Bachelor’s degree in Risk Management, Business, Insurance, or related field (or equivalent experience).
Adjuster license or certifications (e.g., AIC, ARM) a plus.
Experience with self-insured retention (SIR) or captive insurance programs.
Working knowledge of DOT/FMCSA insurance-related regulations.

The expected salary range for this role is $65,000-130,000. The actual base pay offered will be determined on factors such as experience, skills, training, location, certifications, education, and other factors permitted by law. Decisions will be made on a case-by-case basis. In addition to the base salary, this position may be eligible for performance-based incentives.