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Claims Representative II - Floater


We’re looking to staff Claims Representative II Floater positions to join our Personal Lines Non-Standard Auto team. The ideal reps will be team players that have creativity, empathy, interpersonal skills and a strong desire to help.  As a Bodily Injury Claims Representative II of Sentry, you’ll help us commit to our powerful promise to be there for our policyholders when they need us by proving exceptional claims service within our Non-Standard Auto Unit. 

This position can work remotely from home, based on location.

Hiring Part time and Full time.

What You'll Do

As a Claims Representative II Floater, you will be expected to handle the day-to-day tasks on a vacant desk to keep claim files moving and resolving claims in the best interest of the insured, claimant and Sentry. This is to ensure the delivery of quality claim service to our customers, and other parties to a claim, while protecting the assets of Sentry.  You’ll do this by:

  • Handling mail
  • Returning phone calls
  • Sending correspondence
  • Making payments
  • Evaluating and negotiating claims
  • Other claims handling activities

What it Takes

  • Bachelor’s Degree or equivalent work experience
  • 3+ years of related bodily injury claims experience required
  • Knowledge of insurance policies and coverage, claim payment procedures and familiarity with medical terminology
  • Able to make sound decisions while using good judgment in evaluating claims
  • Able to review and interpret complex and detailed documents such as contracts, medical reports, and insurance regulations
  • Ability to handle claims with different coverages, policy types and in multiple states.    
  • Effective oral and written communication skills
  • Able to maintain confidential information
  • Personal computer and math skills beneficial
  • Ability to pass the required coursework applicable to job duties

What You'll Receive

We take great pride in making Forbes’ list of America’s Best Midsize Employers since 2017. A lot of different factors go into that honor, many of which contribute to your job satisfaction.  At Sentry, your total rewards go beyond competitive compensation.  Below are some benefits and perks that you’ll receive.

  • To best support our associates and our culture, Sentry is happy to offer flexibility through a scheduled work from home (Monday and Friday)/in office days (Tuesday through Thursday) after we begin to return to the office.
  • Generous Paid-Time Off plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending.
  • Extensive Work-Life Resources to lend a helping hand.
  • Sentry Foundation gift matching program to encourage charitable giving.
  • Continue your education and career development through Sentry University (SentryU).

How You’ll Apply

If you are interested in joining Sentry’s team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you’ll need to create an account. Please complete your application and upload your resume online.

About Sentry

All of us at Sentry—more than 4,000 associates—have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We’re proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.


Our headquarters is in Stevens Point, Wisconsin, with claims and service 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.


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.


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

Equal Employment Opportunity

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.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Nic LaRosa

Job Title:
Claims Representative II - Floater
Job ID:
Salary Grade:
Chicago, IL
Full/Part Time:
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