Sr. Claims Representative - Transportation (Remote)

Berkley Small Business Solutions (a Berkley Company); West Hartford (CT); Hybrid; USD 80,000 - 110,000; Full time

Benefits offered by this job

Competitive compensation

Excellent benefits

Profit sharing

Job summary

Berkley Small Business Solutions (BSB) in the United States is seeking an experienced claims professional with 5+ years in commercial auto or casualty claims. You will lead complex investigations, evaluate coverage, and mentor junior adjusters while coordinating with insureds, brokers, and internal teams.

The role emphasizes advanced coverage evaluation, high‑stakes negotiation, and ensuring complete documentation. Remote work arrangements may be considered for highly qualified candidates.

Qualifications

• 5+ years of commercial auto or casualty claims handling experience, preferably trucking, cargo, or multi‑jurisdictional claims.
• Demonstrated expertise in coverage interpretation, liability assessment, and negotiation of complex claims.
• Strong interpersonal, communication, and conflict‑resolution skills with the ability to manage sensitive or high‑stakes interactions.
• Advanced organizational and analytical abilities, with proficiency in Microsoft Office and claims management systems.
• Ability to mentor and support development of less experienced adjusters.
• Must obtain and maintain independent adjuster licenses in all required states within 90 days of hire.

Responsibilities

• Lead proactive and timely communication with insureds, claimants, brokers, and internal partners, ensuring clear and accurate explanation of claim findings and resolution strategies.
• Serve as a primary escalation point for complex or sensitive customer issues, providing expert guidance and resolution.
• Oversee vendor performance, including appraisers, independent adjusters, and specialty experts, ensuring timely and high‑quality deliverables.
• Perform advanced coverage evaluations by applying policy language, statutes, regulations, and case law to complex loss scenarios.
• Communicate coverage positions clearly and professionally to all stakeholders, including detailed coverage letters.
• Provide consultative support to junior adjusters on coverage questions and jurisdictional compliance.
• Ensure claim files reflect complete, accurate, and timely documentation supporting all decisions, estimates, and communications.
• Monitor and validate data quality and statutory reporting compliance across assigned files.
• Independently establish and adjust loss and expense reserves on complex and potentially high‑severity claims.
• Identify significant reserve changes early and collaborate with leadership and actuarial teams on trends and emerging risk indicators.
• Mentor junior adjusters on accurate and defensible reserving practices.
• Lead and manage comprehensive investigations through strategic engagement with insureds, witnesses, experts, authorities, and medical providers.
• Conduct or direct recorded statements, scene investigations, and technical evaluations as needed.
• Evaluate and pursue subrogation, contribution, and recovery opportunities, including direct negotiation with carriers and adverse parties.
• Manage claim workflows with disciplined diary practices, ensuring adherence to guidelines and regulatory timelines.
• Direct external vendors in the evaluation of damages, liability assessment, and exposure analysis for complex claims.
• Oversee and resolve total loss claims, including valuation disputes and salvage processes.
• Negotiate settlements on complex claims using advanced techniques and industry expertise.
• Serve as a resource for junior representatives, offering guidance on coverage, investigations, claim strategy, and customer communication.

Skills

Claims handling

Coverage interpretation

Negotiation

Communication

Mentoring

Licensing (Independent adjuster)

Mentor juniors

Data & analytics

Education

Bachelor’s degree preferred

Tools

Microsoft Office

Claims management systems

Job description

Company Details

Berkley Small Business Solutions (BSB) is committed to providing small business customers with the next generation of small business solutions, including offering operational, underwriting, and marketing opportunities. We offer insurance products to Small Business Owners for transportation and other main street businesses. We leverage underwriting expertise, data, and analytics, and automation for risk assessment, selection, pricing retention. We champion our customers, distribution always seeking a smarter way to provide a more efficient and better user experience.

Company Details

Berkley Small Business Solutions (BSB) is committed to providing small business customers with the next generation of small business solutions, including offering operational, underwriting, and marketing opportunities. We offer insurance products to Small Business Owners for transportation and other main street businesses. We leverage underwriting expertise, data, and analytics, and automation for risk assessment, selection, pricing retention. We champion our customers, distribution always seeking a smarter way to provide a more efficient and better user experience.

We are a proud member of W. R. Berkley Corporation, one of the largest commercial lines property casualty insurance holding companies in the United States. With the resources of a large Fortune 500 corporation and the flexibility of a small company, we exclusively work with select independent agents to bring technology solutions that help them build their business.

Responsibilities

• Lead proactive and timely communication with insureds, claimants, brokers, and internal partners, ensuring clear and accurate explanation of claim findings, liability impacts, and resolution strategies.
• Serve as a primary escalation point for complex or sensitive customer issues, providing expert-level guidance and resolution.
• Oversee vendor performance, including appraisers, independent adjusters, and specialty experts, ensuring timely and high-quality deliverables.
• Perform advanced coverage evaluations by applying policy language, statutes, regulations, and case law to complex loss scenarios.
• Communicate coverage positions clearly and professionally to all stakeholders, including issuance of detailed coverage letters.
• Provide consultative support to junior adjusters on coverage questions and jurisdictional compliance.
• Ensure claim files reflect complete, accurate, and timely documentation supporting all decisions, estimates, and communications.
• Monitor and validate data quality and statutory reporting compliance across assigned files and provide corrective guidance when necessary.
• Independently establish and adjust loss and expense reserves on complex and potentially high-severity claims, supported by robust analysis and documentation.
• Identify significant reserve changes early and collaborate with leadership and actuarial teams on trends and emerging risk indicators.
• Mentor junior adjusters on accurate and defensible reserving practices.
• Lead and manage comprehensive investigations through strategic engagement with insureds, witnesses, experts, authorities, and medical providers.
• Conduct or direct recorded statements, scene investigations, and technical evaluations as needed.
• Evaluate and pursue subrogation, contribution, and recovery opportunities, including direct negotiation with carriers and adverse parties.
• Manage claim workflows with disciplined diary practices, ensuring adherence to company guidelines, regulatory timelines, and best-practice standards.
• Direct external vendors in the evaluation of damages, liability assessment, and exposure analysis for complex claims.
• Oversee and resolve total loss claims, including valuation disputes, diminished value considerations, salvage processes, and heavy equipment appraisals.
• Negotiate settlements on complex claims using advanced negotiation techniques and industry expertise.
• Serve as a resource for junior representatives, offering guidance on coverage, investigations, claim strategy, and customer communication.
• Provide informal coaching and contribute to training initiatives as requested.
• Support continuous improvement efforts and department initiatives to enhance claims quality and operational efficiency.
• May perform other functions as assigned.

For a highly qualified candidate, remote working arrangements may be considered.

Qualifications

• 5+ years of commercial auto or casualty claims handling experience, preferably involving trucking, cargo, or multi‑jurisdictional claims.
• Demonstrated expertise in coverage interpretation, liability assessment, and negotiation of complex claims.
• Strong interpersonal, communication, and conflict‑resolution skills with the ability to manage sensitive or high‑stakes interactions.
• Advanced organizational and analytical abilities, with proficiency in Microsoft Office and claims management systems.
• Ability to mentor and support development of less experienced adjusters.
• Must obtain and maintain independent adjuster licenses in all required states (e.g., AL, CT, GA, FL, ME, MS, NY, NC, SC, TN, TX) within 90 days of hire, including completion of coursework, testing, and background checks.

Education

• Bachelor’s degree preferred, or an equivalent combination of education and progressively responsible claims experience.

Additional Company Details

The Company is an equal employment opportunity employer.

The company offers a competitive compensation plan and robust benefits package for full time regular employees.

Base salary & Benefits include Health, dental, vision, life, disability, wellness, paid time off, 401(k) and profit‑sharing plans.

Salary Range: $80k-$110k

The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.

Additional Requirements

Business related travel as required (estimated less than 5% of time)