Demo

Claims Representative Senior - Commercial Liability

Sentry
Madison, WI Full Time
POSTED ON 3/26/2026
AVAILABLE BEFORE 4/26/2026
In this role, you’ll investigate and resolve moderate to complex insurance claims in an efficient and accurate manner.

This position will be located in our Stevens Point, WI - Division Street; Edwardsville, Il; or Madison, WI office under our hybrid work model.

What You’ll Do

As a Senior Claims Representative, you'll provide superior service by conducting prompt claim investigations, which includes evaluating coverage, determining liability, and settlement of damages including those in litigation. In addition, you will:

  • Verify coverages by thoroughly reviewing the policy and interpreting policy terms, conditions, and language, which may require working with coverage counsel.
  • Evaluate complex liability by taking recorded statements from involved parties and witnesses, reviewing police reports, and compiling other pertinent evidence.
  • Analyze all potential exposures, potentially high limit exposures, and resolve claims in the best interest of the insured, claimant, and Sentry.
  • Evaluate physical damages and bodily injury claims, working closely with repair shops, medical providers, automobile appraisers, and/or contractors to facilitate necessary and related services or repair work.
  • Establish timely reserves based on the ongoing liability and damage assessments, negotiating property damage and bodily injury settlements with policyholders, claimants, and attorneys, and other insurance carriers.
  • Manage a case load of litigated and non-litigated automobile, general liability, and product related claims, most of which will be bodily injury files of mid–level severity and complexity. Work with legal counsel and the insured to appropriately review and handle complex time limited demands and the defense of litigated files.
  • Comply with industry regulations, legal requirements, and internal polices through thorough documentation of all decisions, correspondence, and discussions that occur throughout the life cycle of the claim.
  • Obtain and maintain licenses as required.

What It Takes

  • Bachelor’s degree or related experience
  • 3 years of related work experience
  • Thorough claims knowledge of claims and claims processes
  • Ability to review and analyze complex documents, insurance policies, coverages, medical reports, and insurance regulations
  • Ability to make appropriate claim decisions, prioritize, and manage workload
  • Demonstrated effective verbal and written communication skills
  • Ability to handle conflict and negotiate resolutions
  • Technology aptitude

What You'll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you’ll work in office.
  • As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.
  • Meal Subsidy available for associates who report to an office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
  • Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program
  • Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off
  • Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.
  • Well-being and Employee Assistance programs
  • Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Joe Larsen

Talent Acquisition Specialist Sr

Joe.Larsen@sentry.com

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 Senior - Commercial Liability in Madison, WI
$66,656 to $84,550
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