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Operations Supervisor


Sentry is seeking an individual that thrives in an environment where they are providing exceptional guidance and direction to operations associates. Our team supports varied policy administration and underwriting services to a wide range of internal and external customers including, but not limited to insureds, agents/brokers, underwriters, sales producers, and other Commercial Lines business departments.

What You'll Do

As an Operations Supervisor supporting our Commercial Lines, you will: 

  • Ensures that production schedules are met, and that service and quality standards are attained in an efficient and cost-effective manner.
  • Oversee the development of staff and implementation of appropriate training and cross training programs.
  • Works with associates to resolve workers compensation bureau criticisms, along with auto and workers compensation reporting errors to ensure customers are not negatively impacted and to eliminate or reduce fines assessed to Sentry.
  • Monitors quality through a monthly quality audit process and, measures service and productivity through various unit reports.
  • Provides management with regulatory reporting for state compliance audits.
  • Recommends workflow procedures that assist the associates to be more efficient in their daily operations
  • Responsible for development, coordination, and implementation of cross training programs for the associates and workflow efficiency.

What it Takes


  • Minimum 2 years of related work experience
  • Bachelor’s Degree or equivalent work experience
  • Knowledge of Sentry organization and distribution systems.
  • Self-motivated.
  • Ability to motivate and develop direct reporting staff to provide efficient and cost-effective services.
  • Demonstrated technical knowledge in assigned processing/service area.
  • Analytical skills to identify, evaluate and develop procedures for problem resolution.
  • Organizational, human relation and communication skills.
  • Good understanding of business communications, computer, word processors, and various software applications 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.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Jennifer Van Vlack

Job Title:
Operations Supervisor
Job ID:
Salary Grade:
Montgomery, AL
Full/Part Time:
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