Demo

Claims Representative - Entry Level

Sentry
Stevens, WI Full Time
POSTED ON 9/26/2026
AVAILABLE BEFORE 10/25/2026
Join our Commercial Auto team by leading claim investigations, assessing liability, and driving fast, fair resolutions for policyholders.

An entry-level Claims Representative position requires a learning nature, empathy and interpersonal skills along with a strong desire to assist customers.

We're currently recruiting for a Claims Representative to work within our Commercial Auto & Equipment team.

This role will be filled following our hybrid work model at our Stevens Point, WI offices. This role is NOT available for remote work.

What You'll Do

As a Claims Rep - Entry Level, You Will

  • Gain knowledge to verify coverage, compensability, and reasonable payments by thoroughly reviewing the policy, reviewing accident details, and other pertinent information related to the claim.
  • Develop investigative claims skills by taking and reviewing recorded statements from involved parties and witnesses, reviewing police reports, and other pertinent evidence.
  • Build knowledge to evaluate claims exposure appropriately, establishing timely reserves.
  • Comply with industry regulations, legal requirements, and internal company policies through thorough documentation of all decisions, correspondence, and discussions that occur throughout the life cycle of the claim.
  • Support customers with empathy and understanding, assisting them through difficult situations and effectively communicating the claims process, ongoing claim status, and decisions, including the reasoning behind them.
  • Ability to obtain and maintain state licensing requirements.

What It Takes

  • Bachelor’s degree or equivalent work experience
  • Previous insurance related and/or customer service experience is preferred.
  • Ability to professionally communicate verbally and in writing
  • Ability to exercise effective time management skills.
  • Shows technological aptitude.
  • Associates must have the ability to travel as necessary to satisfactorily complete their job responsibilities as assigned.

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!

Tha Xiong

Tha.Xiong@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 - Entry Level in Stevens, WI
$35,204 to $40,059
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