Underwriter Associate - Trainee

Seeking a detail-oriented, intuitive problem solver to join our Commercial Lines Underwriter training program, an ideal entry point for an underwriting career.

We are currently seeking an individual who is a detail oriented, intuitive thinking problem solver to join our Commercial Lines Underwriter training program. If you are looking for a career in underwriting, this could be the right opportunity for you!

This is a hybrid position, requiring Tues-Thurs in-office in Charlotte, NC. Mondays and Fridays can be worked from home.

This position will begin in June 2026.

What You’ll Do

As a participant in our Underwriter Trainee Program, you will go through a 6-month structured program to learn how to evaluate commercial lines accounts including all property/casualty lines of business.  You will determine appropriate coverage terms, decide upon a pricing strategy and work with agents to complete insurance transactions for new and renewal business.

During the 6 months of scheduled training, you will:

• Complete coursework on standard industry coverage forms and basic insurance topics.

• Participate in interactive virtual and in person sessions with extensive use of actual accounts as case studies.

• Attend 3 separate 3-day sessions in our Home Office in Stevens Point, Wisconsin

• Work actual accounts in consultation with your mentor underwriter 

Following the 6 month program, in collaboration of your mentor/local managers you will begin working with increased underwriting authority and autonomy with the expectation to become a productive, independent commercial lines underwriter with standard authority within 12 months of starting the program. 

What it Takes

• Bachelor’s Degree or equivalent experience.  Risk management, Insurance or Finance degrees preferred

• Prior insurance related work or internship helpful, but not required

• PC skills in programs such as Microsoft Office including Word, Excel, and Access

• Excellent verbal, written and interpersonal communication skills along with analytical and mathematical skills

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!

Associate Talent Acquisition Specialist

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.