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Director of Casualty Claims - Commercial Lines

Remote / Online - Candidates ideally in
Stevens Point, Portage County, Wisconsin, 54481, USA
Listing for: 001 Sentry Insurance Company
Full Time, Remote/Work from Home position
Listed on 2026-09-03
Job specializations:
  • Insurance
    Risk Manager/Analyst
Salary/Wage Range or Industry Benchmark: 90000 - 150000 USD Yearly USD 90000.00 150000.00 YEAR
Job Description & How to Apply Below

Lead claims associates to drive compliant, timely resolutions, expense control, and superior customer service. Govern settlement authority and direct staff training.

What You’ll Do:
  • Lead and Develop Leaders:
    Provide strategic oversight and mentorship to your management team, fostering a high‑performing culture centered on continuous learning, accountability, and the ongoing upskilling of technical proficiency across diverse claim scenarios.
  • Guide Financial and Technical Outcomes:
    Navigate complex authority reserving requests and provide expert settlement and negotiation guidance, ensuring equitable, timely, and compliant resolution of claims while managing expenses to support profit and growth objectives.
  • Drive Strategic and Regulatory Compliance:
    Spearhead strategic initiatives related to claim operations, regulatory compliance, and internal best practices, establishing robust management controls, audit standards, and protocols to achieve departmental objectives.
  • Optimize Workflows with Technology:
    Continually evaluate and identify opportunities to streamline claim workflows and processes utilizing technology‑enabled solutions to drive operational efficiency and modernization.
  • Shape Policy and Systems:
    Collaborate on objective setting, the development of claims policies, and the implementation of necessary systems to support seamless claim handling and adherence to departmental standards.
  • Oversee Audits and Governance:
    Oversee department and corporate audits by managing communications, supplying requested data, providing supporting documentation, and addressing audit findings to ensure successful completion.
  • Represent Sentry Externally:
    Act as a brand ambassador, representing the company in industry associations, committees, boards, and bureaus.
What it Takes:
  • Bachelor’s degree or equivalent work experience, Juris Doctor preferred
  • 8+ years of related work experience, with successful and increasingly responsible management and leadership experience, including broad background in claims, including exposure to multiple lines of coverage and policies, preferably in commercial auto, transportation, and general liability
  • Strong analytical, communication, and human relations skills
  • Knowledge of Sentry's philosophies, products, and systems
  • Technical expertise in assigned area of claim policies and practices as well as insurance products
  • Knowledge of applicable laws affecting claims; preferably technical expertise
  • Strong working knowledge of contracts, service level agreements, and application of terms and conditions
  • Strong negotiation skills
Here is what you can look forward to as part of our team:
  • Hybrid Flexibility:
    Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.
  • Dining on Us:
    Depending on your location, we may provide a stipend that can be used at our on‑site cafeteria or a meal allowance to keep you fueled.
  • Continuous Learning:
    Unlock your potential through Sentry University and take advantage of our tuition reimbursement program.
  • Comprehensive Benefits:
    We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources.
  • Options for HSA, FSA, and Dependent Care FSA are available.
  • Work-Life Balance:
    Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
  • Investing in Your Future:
    We’re committed to your long‑term financial well‑being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
  • Giving Back:
    Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
Why Join Sentry?

At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s…

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