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Sr. Claims Representative - Transportation; Remote

Remote / Online - Candidates ideally in
West Hartford, Hartford County, Connecticut, 06107, USA
Listing for: Berkley Small Business Solutions (a Berkley Company)
Full Time, Remote/Work from Home position
Listed on 2026-09-14
Job specializations:
  • Insurance
    Insurance Analyst, Underwriter, Risk Manager/Analyst, Insurance Claims
Salary/Wage Range or Industry Benchmark: 80000 - 110000 USD Yearly USD 80000.00 110000.00 YEAR
Job Description & How to Apply Below

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…
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