Direct Writer-Program Specialist
Confirmed on the employer's own hiring board on Oct 1, 2026. First seen by Alion on Sep 24, 2026.
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
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.