Demo

Claims Representative - Liability

Sentry
Madison, WI Full Time
POSTED ON 10/9/2026
AVAILABLE BEFORE 11/14/2026
You will investigate and resolve insurance claims with a focus on accuracy, efficiency, and fair resolution and independently manage caseloads and negotiate settlements.

What You'll Do

As a Claims Representative-Liability, you will:

  • Verify coverage by thoroughly reviewing the policies and interpreting policy terms, conditions and language.
  • Evaluate liability by taking recorded statements, reviewing police reports, and compiling other pertinent evidence. Negotiate or deny liability based on the investigation outcome.
  • Evaluate physical damage and bodily injury claims based on estimates, photos, appraisals, medical reports, medical bills, and other evidence. Working closely with medical providers, repair shops and/or contractors to facilitate necessary and related services.
  • Set appropriate claim reserves in a timely manner based on ongoing evaluations of liability. Negotiate bodily injury settlements with policyholders, claimants, attorneys, and other insurance carriers to reach fair resolutions within established guidelines. Ensure claims are paid promptly and within authorized limits.
  • Ensure compliance with industry regulations, legal requirements, and internal policies by thoroughly documenting all decisions, communications, and activities throughout the entire claims process.
  • Provide empathetic and supportive service to customers as they navigate challenging situations, clearly explaining the claims process, keeping them informed of their claim process, and communicating decisions along with the reasoning behind them.
  • Ability to obtain and maintain state licensing requirements

What It Takes

  • Bachelor’s degree or equivalent work experience
  • Minimum 1 year of related work experience
  • Prior attorney rep experience highly preferred
  • Ability to review and analyze detailed documents, insurance policies, coverages, medical bills and records
  • Ability to make appropriate claim decisions, prioritize, and manage workload; time limit demands
  • Effective verbal and written communication skills
  • Demonstrated fundamental negotiation skills

Here is what you can look forward to as part of our team:

At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.

  • 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 Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.

Building on a Legacy

Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A rating from A.M. Best, the industry’s leading authority, for over 30 years.

Your Career, Our Community

Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.

Ready to own your future? Join us at Sentry, opportunities await!

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

Salary.com Estimation for Claims Representative - Liability in Madison, WI
$74,412 to $93,175
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Claims Representative - Liability?

Sign up to receive alerts about other jobs on the Claims Representative - Liability career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$66,419 - $85,011
Income Estimation: 
$80,544 - $105,138
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Sentry

  • Sentry Watertown, SD
  • About the Position Sentry is looking for a Part-Time Fabrication Intern to join our manufacturing team in Watertown. This is a hands-on position for someon... more
  • 7 Days Ago

  • Sentry Davenport, IA
  • You will investigate and resolve insurance claims with a focus on accuracy, efficiency, and fair resolution and independently manage caseloads and negotiat... more
  • 7 Days Ago

  • Sentry Stevens, WI
  • Administer specialty insurance programs, service insureds, process requests, and coordinate monthly updates with John Deere. The role will be staffed at ou... more
  • 7 Days Ago

  • Sentry Stevens, WI
  • Our Event and Meeting Planners provide effective project management support of meetings and events. What You'll Do Develop and implements all aspects of sm... more
  • 7 Days Ago


Not the job you're looking for? Here are some other Claims Representative - Liability jobs in the Madison, WI area that may be a better fit.

  • TEKsystems Prairie, WI
  • Description The Transactional Liability Claims Professional is responsible for managing a portfolio of complex Transactional Liability claims, including Re... more
  • 1 Day Ago

  • Wisconsin Municipal Mutual Insurance Company Madison, WI
  • About WMMIC At Wisconsin Municipal Mutual Insurance Company (WMMIC), we believe how we work is just as important as what we do. We are built on trust, resp... more
  • 20 Days Ago

AI Assistant is available now!

Feel free to start your new journey!