Demo

Operations Technician Sr. - Transportation & Regional

Sentry
Stevens, WI Full Time
POSTED ON 11/8/2026
AVAILABLE BEFORE 12/15/2026
This position will be located in our Sentry Strongs office in Stevens Point, WI.

The Operations Technician Senior will support commercial lines (CL) operational and underwriting processes within guidelines by handling a variety of basic to moderately complex policy transactions that support the review and acceptance/decline of new or renewal CL business. This team member assists on behalf of underwriting, claims, and agents, compiles and/or shares policy and coverage for assigned lines of business and customers. They will ensure proper documentation and records management according to regulatory and Sentry standards.

What You'll Do

  • Provide operations support, including processing of new and renewal transactions and policy updates
  • Perform moderately complex operations support duties and handle production problem listings
  • Utilize various systems and sites to manage and process requests related to the Transportation and Regional businesses
  • Use problem-solving skills and best judgment to work with internal business units to resolve problems and provide insight about service
  • Use your skills in multitasking, time management and attention to detail

What It Takes

  • May provide testing of new or revised procedures as it relates to the business systems. May assist with procedure writing
  • May assist in training and quality auditing of new operation technician seniors
  • Refers questions outside of responsibility/authority
  • Performs other job-related duties as assigned from time to time

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!

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.

Salary.com Estimation for Operations Technician Sr. - Transportation & Regional in Stevens, WI
$50,998 to $61,820
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