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Direct Writer-Program Specialist

Sentry Insurance · Stevens Point, WI · Full time

Posted Sep 24, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you built a spreadsheet report that someone else used to make a decision.

What they are checking: Whether they think about the reader and the decision, since management uses these program reports to evaluate programs.

Tell me about a time you had to handle a lot of detail work accurately under a deadline.

What they are checking: Whether their accuracy holds up under time pressure, since monthly updates and commission reports both have fixed dates.

This role is hybrid at the Stevens Point home office and not remote. How does that fit with how you like to work?

What they are checking: Whether they have accepted the in-office requirement so it does not become a problem later.

What would you do

A John Deere dealer calls with a coverage question, a quote request and a billing issue all in one call. How do you handle it?

What they are checking: Whether they can keep several requests straight on one call and close each one without dropping any.

You notice a system supporting the dealer programs is producing wrong data. Who do you go to, and what do you do in the meantime?

What they are checking: Whether they escalate system issues clearly while protecting customers from the bad output in the meantime.

An insured is upset because a renewal premium went up and they want it fixed today. How do you respond?

What they are checking: Whether they can stay calm, explain what they can, and route underwriting questions properly without promising outcomes.

You may attend trade shows for the dealer programs. How would you represent the program to a dealer you've never met?

What they are checking: Whether they can explain the program plainly and build a working relationship with a dealer partner.

About the work

You reconcile financials between John Deere Financial and Sentry for the UltraGard and Floater programs. Walk me through how you'd approach a reconciliation that's off by a small amount.

What they are checking: Whether they treat a small variance as a real problem to trace rather than something to plug.

What's the difference between a policy change, a cancellation and a loss run request, and why does each one matter to the customer?

What they are checking: Whether they know basic policy servicing terms well enough to answer customers accurately.

You maintain agent appointments and generate commission reports. What could go wrong if an appointment lapses or a commission is wrong?

What they are checking: Whether they understand the compliance and relationship cost of small administrative errors with agents.

What underwriting tasks have you done before, even small ones, for new business, renewals or cancellations?

What they are checking: Whether they have hands-on experience following underwriting rules or will need to learn the basics from scratch.

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The full job description

As published by Sentry Insurance.

Administer specialty insurance programs, service insureds, process requests, and coordinate 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 • Ability to pass/maintain the respective state's Property and Casualty licensing exam(s) within 120 days of hire and meet continued education requirements as required for the position • Experience in the use of office and business software applications. Demonstrated experience in creating custom reports. • Prior Commercial Lines insurance experience desired with knowledge of Commercial Lines products and/or underwriting guidelines • Ability to interpret and apply commercial insurance concepts and underwriting guidelines for majority of positions beneficial • Effective organizational, human relations, and communications skills. • Knowledge of Sentry’s insurance operations and philosophies. • Strong critical thinking and analytical skills. 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! Casey Van Der Geest Talent Acquistiion Specialist Casey.VanDerGeest@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.

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