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Retirement Plan Project Manager

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 project that started to slip. How did you get it back on track?

What they are checking: Whether they spot delays early and act, rather than just report them.

Tell me about a time you used customer feedback to improve a product or process.

What they are checking: Whether they act on feedback, which the posting lists as a source of improvements.

What would you do

How would you support a sales producer who is trying to win a small business 401(k) and has technical questions about the plan?

What they are checking: Whether they can translate plan rules into help that wins and keeps business.

How do you explain a product change to stakeholders ranging from executives to field producers?

What they are checking: Whether they can tailor communication to very different audiences.

Two teams disagree about whether to delay a release to add a feature. How do you help them reach a decision?

What they are checking: Whether they can surface tradeoffs and drive a decision without owning the teams.

About the work

What is your experience with 401(k) plans, and which parts of plan design or administration do you know best?

What they are checking: The depth of technical retirement plan knowledge the role leans on.

Walk me through how you track a project with several IT and business teams so it stays on time and in scope.

What they are checking: Whether they have real methods for keeping projects on track when many teams own pieces of the work.

How would you research what competitors are offering in the small business 401(k) market?

What they are checking: Their approach to market and competitive analysis that informs product decisions.

Which metrics would you watch to know if a retirement product is performing well?

What they are checking: Whether they think about growth, retention and profitability, as the posting names.

How do you stay current on retirement plan regulations and rule changes?

What they are checking: Whether they keep their technical knowledge current in a heavily regulated area.

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The full job description

As published by Sentry Insurance.

In this role, you will provide technical knowledge & support during the sales of 401(k) products to achieve growth, retention & profitability among Sentry Direct Writer sales producers. This position will be located at our office in Stevens Point, WI, Madison, WI, Davenport, IA or El Paso, TX in a hybrid work model and is not a fully remote opportunity. For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. What You'll Do As a Senior Retirement Plan Analyst , you’ll leverage your technical retirement plan knowledge and experience in the development and marketing of 401(k) products. Along with this responsibility you will: • Provide project coordination and support including, but not limited to tracking and coordination of various projects and initiatives ensuring the on-time and in-scope delivery of assigned projects • Deliver department level projects or assist with cross-department projects, typically involving multiple teams across IT functions or business areas • Communicate product updates, progress, and challenges to stakeholders at all levels • Conduct market research, competitive analysis, and customer feedback analysis to identify new product opportunities and enhancements • Monitor product performance, analyze key metrics, and iterate on products to achieve business goals What it Takes • Bachelor’s Degree or equivalent work experience • 5+ years of related 401(k) industry experience • Experience and knowledge in retirement product development, project management and strategic project leadership • Experience and knowledge in the marketing of group and 401(k) products, business to business communications, and sales cycle beneficial • Industry coursework such as CAPM, PMP, QPFC, CPFA, QKA, ARPC, AIF, AIFA, or CFP beneficial • Knowledge of qualified retirement plan and group benefit insurance products • Proficient with working in Microsoft Power Point and Excel • Highly effective interpersonal, communication, and presentation 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 Acquisition 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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