Website Sentry Insurance


At Sentry, our priority is providing exceptional customer service and we currently have an opening for you to join this exciting team.  This is a great opportunity to start or grow your career in a fun, team-focused environment, while facing new challenges to develop professionally.  We’re looking for qualified candidates who will thrive on the front lines by providing stellar service to our customers over the phone.  Bring your strong critical thinking skills and a “can do” attitude to this fast-paced position.

Our customers often face concerns or questions outside of normal business hours.  To meet this need, our call centers are open from 7am – 10pm Monday through Saturday and Sundays 7am – 5pm.   As a Customer Service Representative, you will be a key factor in helping our customers by having flexibility to work during these hours.

Take the customer service skills you have acquired over the years to the next level or make a change and start down your new career path today with our growing team of Service Professionals at one of the largest mutual insurance companies in the U.S!

**Currently we are offering a sign on bonus of $1000 to bilingual (Spanish) new hires and non-bilingual new hires are eligible for a $500 sign on bonus.

What You’ll Do

As a Customer Service Representative, you’ll work within our Non-Standard Auto and Motorcycle customer call center to provide outstanding customer service by responding to inbound calls.   Additionally, you’ll:

Handle a high volume of phone calls from agents and customers
Perform pre-underwriting screening
Verify coverage, evaluate submitted bills, and authorize payments
Advise customers of billing policies and procedures and process policy changes
Resolve customer inquiries and maintain customer relations
Complete administrative tasks and input customer information into databases for documentation

What it Takes

High School degree or equivalent work experience
Call center experience or a customer service background preferred
High level of accuracy with data entry
Capable of communicating difficult news
Flexibility to work during call center hours, must be available to work until 9 pm during week days and have availability to work on Saturdays
Ability to multi-task prioritizes, communicate effectively and remain organized
Good working knowledge of PC based computers and familiar with Microsoft Office
Bilingual (English-Spanish) skills a plus
Underwriting and Rating knowledge beneficial

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.

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