Remote Transportation Insurance Jobs in Illinois

Good Things Start Here.

Good things are happening at Berkshire Hathaway GUARD Insurance Companies-an A+ (Superior) rated, nationwide Property & Casualty insurer backed by Berkshire Hathaway. With supportive leadership, collaborative teams, and opportunities to grow, GUARD is a place where people build meaningful, longterm careers.

Good Things You Can Count On.

• Hybrid schedule: 2 days remote / 3 inoffice
• Predictable hours (no nights, weekends, or holidays)
• Competitive pay + generous PTO
• Medical, dental & vision starting day one
• 401(k), tuition reimbursement & longevity bonuses

Berkshire Hathaway GUARD Insurance Companies is seeking a Trucking Specialist to join our P&C Casualty Claims team. Reporting to the Director of Claims, this role is responsible for investigating, evaluating, and resolving complex commercial trucking liability claims, with a strong emphasis on litigated, high-severity bodily injury, catastrophic injury, and fatality exposures.

Key Responsibilities

• Investigate, evaluate, and resolve complex trucking liability claims involving severe bodily injury, catastrophic losses, fatalities, and significant exposure.
• Manage a caseload of litigated trucking claims from initial assignment through resolution, including trial preparation and settlement negotiations.
• Review policy language and coverage issues, coordinating with coverage counsel when necessary.
• Develop liability assessments and damage evaluations based on accident investigations, medical records, expert reports, and other claim documentation.
• Direct and manage defense counsel, independent experts, accident reconstructionists, and other vendors to support claim strategy.
• Establish litigation plans, monitor legal expenses, evaluate venue exposure, and develop settlement recommendations.
• Participate in mediations, settlement conferences, and other alternative dispute resolution proceedings.
• Communicate effectively with insureds, claimants, attorneys, law enforcement, and other stakeholders throughout the claim lifecycle.
• Maintain accurate claim documentation and ensure compliance with internal claim handling standards and regulatory requirements.
• Participate in file reviews, claim roundtables, and training initiatives focused on complex casualty and trucking litigation.

• 3+ years of experience handling commercial trucking liability claims, including significant litigation exposure.
• Demonstrated experience managing high-severity bodily injury, catastrophic injury, wrongful death, and other complex casualty claims arising from trucking accidents.
• Strong litigation management experience, including directing defense counsel, evaluating legal strategies, participating in mediations, and negotiating substantial settlements.
• Knowledge of trucking operations, FMCSA/DOT regulations, transportation liability, and multi-state claims handling.
• Proven ability to assess liability, evaluate damages, establish reserves, and make sound coverage and settlement recommendations on complex claims.
• Experience working with experts such as accident reconstructionists, medical professionals, and forensic specialists.
• Strong analytical, negotiation, and decision-making skills.
• JD preferred, or bachelor's degree (or equivalent experience) in insurance, risk management, law, or a related field.
• Licensing Requirement: Candidates must hold an active adjuster license or be willing and able to obtain and maintain all required state licenses. The company will support the licensing process, including training and compliance with ongoing continuing education requirements.

Salary Range

$90,000 - $150,000 + performance-based bonus

In accordance with applicable pay transparency laws, this range represents a goodfaith estimate. Final compensation will be determined based on factors such as experience, credentials, geographic location, and other considerations permitted by law.

This role may be based out of any of our office locations, including:

New York, NY; Parsippany, NJ; Conshohocken, PA; WilkesBarre, PA; Alpharetta, GA; Rosemont, IL; Plano, TX; Scottsdale, AZ; and Rancho Cordova, CA.