Demo

Claims Representative Specialist - Commercial Lines

Sentryinsurance
Madison, WI Full Time
POSTED ON 6/20/2026
AVAILABLE BEFORE 7/18/2026
A highly experienced adjuster managing a caseload of complex claims, including litigation, to resolution.

This position will report to a Sentry office under our hybrid work model.

As a Claims Representative Specialist on one of Sentry's Commercial Liability teams, this highly experienced claims adjuster will provide prompt claim investigation, evaluation, and settlement or denial of highly complex claims including those in litigation. The claims involve, but are not limited to, general liability and commercial auto losses. In addition, you will...

What You'll Do:

  • Verify coverages and perform coverage investigations including issuing reservation of rights and/or disclaimers

  • Investigate losses and negotiate claims settlements with claimants and their legal representative within assigned authority limits

  • Manage investigative process by taking recorded statements, obtaining investigative reports, evaluating damages or eligibility for benefits, and determining legal responsibility

  • Prepare and present claims for discussion among the commercial claim leadership team as part of Sentry's collaborative escalation process

  • Maintain accurate documentation of investigative facts and decisions that occur during the investigation, evaluation, or resolution processes.

  • Strategize with defense counsel to defend our insureds in business related liability exposures

  • Assist the claims team with training and providing technical claims knowledge

What it Takes:

  • Bachelor's degree or equivalent work experience

  • 5 years of related work experience, with experience in handling transportation claims preferred

  • Extensive claims knowledge with ability to understand and manage litigated claims

  • 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

  • Advanced writing, communication, and presentation skills

  • Advanced conflict resolution and negotiation skills

  • Technological 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

Senior Talent Acquisition Specialist

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 Specialist - Commercial Lines in Madison, WI
$79,989 to $101,405
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