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Salary
≈ $89k – $166k per year (Estimated)
Location
Hybrid (El Paso, Madison, United States)
Seniority
Senior · 5+ years exp
Employment
Full-Time

Confirmed on the employer's own hiring board on Oct 23, 2026. First seen by Alion on Sep 24, 2026.

Overview
Company
Impact
Profile match
Sentry Insurance is a US insurer offering business insurance, 401(k) plans and employee benefits. It hires account executives, litigation adjusters, software engineers and hospitality staff for its SentryWorld campus. The company is headquartered in Stevens Point, Wisconsin, United States.
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

[email protected]

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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