Demo

Transition Services Specialist - 401K

Sentry
Stevens, WI Full Time
POSTED ON 9/27/2026
AVAILABLE BEFORE 10/24/2026
Our 401K team is looking for a Transition Service Specialist to help aide the cancellation or discontinuance of plans.

This individual will coordinate the cancellation or discontinuance to a new provider of plans following established procedures and contractual provisions while maintaining compliance with applicable IRS and/or DOL regulations.

What You'll Do

  • Process the cancellation of plans for contracts, including investment-only contracts.
  • Communicate with employers throughout the plan termination process
  • Ensure that contract and service agreement requirements are met and that assets are distributed in a timely manner as elected by the contract-holder, plan participants, and the contract
  • Makes the system needed changes to ensure that sales credits, contract counts, and service commitments are properly completed or closed out

Additionally, You Will

  • Work closely with Client Services Team
  • Check for complex processes such as 5500 fund preparation, plan year end reviews, compliance testing for plan and contract cancelation
  • Performs quality audits and accurately repots findings to appropriate individuals
  • Performs other job-related duties as assigned from time to time

What It Takes

  • High school diploma or a minimum of 1 year of related work experience
  • Previous experience in 401K plan administration is strongly preferred
  • Effective communication, human relations, and organizational skills
  • Demonstrated understanding of 401K/retirement plan administration including the knowledge of related IRS/DOL regulations
  • Professional development courses through CEBS, ASPPA, or other resources are beneficial

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!

Amelia Sacco

Amelia.Sacco@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.

Salary.com Estimation for Transition Services Specialist - 401K in Stevens, WI
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