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Insurance Program Specialist-Direct Writer

Sentry Insurance
life insurance, parental leave, tuition reimbursement, remote work
United States, Wisconsin, Stevens Point
1800 North Point Drive (Show on map)
May 15, 2026
Administer specialty insurance programs, servicing insureds, processing requests, and coordinating monthly updates with John Deere.

The role will be staffed at our Sentry Home Office in Stevens Point, WI following the hybrid work model. This role is NOT available for remote work.

What You'll Do

  • Respond to a variety of customer calls including, but not limited to coverage questions, quotes for new/additional coverages, policy change, cancellation and loss run requests and billing questions.
  • Maintain agent appointments, distributes agent materials and generates agent commission reports.
  • Create, analyze & distribute statistical spreadsheets for John Deere programs. Reports are provided to Direct Writer management for the purposes of review and evaluation of supported programs.
  • Maintain applicable systems to support the dealer programs and products by monitoring and collaborating with the appropriate areas when issues arise.
  • Reconcile and balance financials between John Deere Financial and Sentry for the UltraGard, and Floater programs.
  • Complete necessary underwriting tasks related to the issuance of new policies, renewals changes and cancellations.

Additional Responsibilities

  • Fulfills needed agent point of sale materials.
  • May attend related trade show and/or industry events.
  • Serves as a point of contact for business processes issues related to the program.

What it Takes

  • Bachelor's Degree or equivalent work experience
  • Minimum 2 years of related work experience
  • Strong preference to have P&C license
  • Experience in the use of office and business software applications. Demonstrated experience in creating custom reports.
  • Effective organizational, human relations, and communications skills.
  • Knowledge of Sentry's insurance operations and philosophies.
  • Strong critical thinking and analytical skills.

What You'll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits andperksthatyou'llreceive.

  • Sentry is happy to offerflexibilitythrough a scheduled Hybrid work model.Monday and Friday work from homeif you choose to, Tuesday through Thursdayyou'llwork inoffice.
  • 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 yourstart,Sentry willprovide equipmentfor your home office.
  • Meal Subsidyavailable for associates who report to an office.
  • 401(K)planwith adollar for dollarmatch on yourfirst eight percent,plus immediate vesting to help strengthen your financial future.
  • Continue your education and career development through Sentry University (SentryU) andutilizeourTuition Reimbursementprogram
  • Generous Paid-Time Off plan for you to enjoy time out of the office as well asVolunteer-Time off
  • Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellnessbenefitsto encourage a healthy lifestyle.
  • Well-being andEmployee Assistanceprograms
  • Sentry Foundationgift matchingprogram to encourage charitable giving.

About Sentry

We takegreat pridein making Forbes' list of America's Best Midsize Employers. A lot ofdifferent factorsgo into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a longtrack recordof 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'reone of the largest and financially strongest mutual insurance companies in the United States.We'rerated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with officeslocatedthroughout 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!

Talent Acquisition Specialist

Shea Supa

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.

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