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Retirement Jobs in Wisconsin (NOW HIRING)

Sentry Insurance

Retirement Plan Analyst

Madison, WI · Hybrid

What You'll Do As a Retirement Plan Analyst, you'll play a key role in assisting our sales producers with the sales of our 401(k) products. Along with this responsibility, you'll: * Act as one of the ...

UMB Financial

Retirement Client Advisor

Milwaukee, WI · On-site

$141K - $207K/yr

The Retirement Client Advisor generates new business opportunities and manages a customer portfolio defined in the business plan. This involves being the primary contact for new or existing customers ...

M3 Ins

Retirement Plan Manager II

Madison, WI · On-site

$70 - $90/hr

As a Retirement Plan Manager II, you will utilize your retirement plan knowledge and professional communication skills to serve as a primary point of contact for clients, maintain and grow ...

UMB Financial

Tax-Retirement Analyst III

Milwaukee, WI · On-site

$51K - $75K/yr

As the Tax-Retirement Analyst III , you will assist in training and act as mentor for associates in Tax and Retirement Analyst I and II positions. You will review the work of Tax and Retirement ...

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Showing results 21-40

All JobsRetirement JobsRetirement Jobs in Wisconsin

Retirement information

See Wisconsin salary details

$31.8K

$63.3K

$100.9K

How much do retirement jobs pay per year?

As of Sep 6, 2026, the average yearly pay for retirement in Wisconsin is $63,266.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,400.00 and $66,600.00 per year, depending on experience, location, and employer.

What are retirement jobs?

Retirement jobs are employment opportunities that individuals pursue after reaching the traditional age of retirement, often to stay active, supplement their income, or explore new interests. These jobs can be part-time, flexible, or seasonal, and may be in fields that the individual is passionate about or wants to try for the first time. Common retirement jobs include consulting, tutoring, retail work, volunteering, and freelance roles. Many retirees choose these positions for social engagement, mental stimulation, and additional financial security.

What are the key skills and qualifications needed to thrive as a retirement planner, and why are they important?

To thrive as a Retirement Planner, you need a strong understanding of financial planning, investment strategies, and retirement regulations, often supported by a degree in finance or a related field and certifications like CFP or ChFC. Proficiency with financial planning software, portfolio management tools, and tax planning systems is essential. Excellent communication, empathy, and problem-solving skills help build trust and tailor plans to clients’ unique needs. These skills ensure clients receive sound, personalized guidance for achieving their retirement goals and long-term financial security.

What challenges might a retirement planner face when helping clients prepare for retirement?

Retirement Planners often encounter challenges such as addressing clients’ unrealistic expectations about retirement savings, navigating complex tax and investment regulations, and helping clients adapt to unexpected life changes. Building trust and communicating effectively are critical, as clients may have concerns about outliving their savings or making the right investment choices. Retirement Planners must stay current with industry trends and regulations to provide sound advice, and they frequently collaborate with other financial professionals to ensure a comprehensive retirement strategy.

What is the difference between Retirement vs Pension Specialist?

AspectRetirementPension Specialist
CredentialsVaries; often includes financial or retirement planning certificationsTypically requires financial, actuarial, or pension-specific certifications
Work EnvironmentFinancial planning firms, retirement communities, or HR departmentsInsurance companies, pension funds, or consulting firms
Industry UsageBroadly used in personal finance and HR contextsSpecialized in pension plan management and consulting
Common Search/ComparisonRetirement vs Pension Specialist

While both roles relate to retirement planning, a Retirement professional offers broader financial advice for retirement, whereas a Pension Specialist focuses specifically on pension plan management and consulting. The Pension Specialist often has specialized certifications and works within pension funds or insurance companies, making their role more niche compared to the general retirement planning services provided by Retirement professionals.

What are the most commonly searched types of Retirement jobs in Wisconsin?

The most popular types of Retirement jobs in Wisconsin are:

What cities in Wisconsin are hiring for Retirement jobs?

Cities in Wisconsin with the most Retirement job openings:

Retirement jobs near you
Infographic showing various Retirement job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 80% Full Time, 14% Part Time, and 5% Contract. Highlights an 92% Physical, 1% Hybrid, and 7% Remote job distribution, with an average salary of $63,266 per year, or $30.4 per hour.

Retirement Plan Analyst

Sentry Insurance

Stevens Point, WI • Hybrid

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 2 days ago

Sentry Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 46 frontline employees who took The Breakroom Quiz

72nd of 315 rated insurance

Job description

Sentry employees have been helping individuals and businesses build and protect their future since 1904 and we are looking for you to join our team as a Retirement Plan Analyst. In this position, you will provide technical knowledge and support during the sales of 401(k) products to achieve growth, retention and profitability among Sentry direct writer sales producers.

This position will be located at our Home Office in Stevens Point, WI or at our office in Madison, WI in a hybrid work model (Monday and Friday work from home if you choose, Tuesday through Thursday required to be in office).

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 Retirement Plan Analyst, you’ll play a key role in assisting our sales producers with the sales of our 401(k) products. Along with this responsibility, you’ll:

  • Act as one of the primary contacts for our team of sales producers and management to ask questions regarding products and sales/marketing programs

  • Assist in the sale of 401(k) and group products primarily through phone consultations and training presentations

  • Create and analyze reports reflecting pre-sale and post-sale efforts in the field to enhance our initiatives to promote future sales and enhance our overall customer experience

  • Provide resource information on investment options, product information, and plan design to the field on individual cases to assist in new 401(k) and group sales

What it Takes

  • Bachelor’s Degree or equivalent work experience

  • 2+ years of related 401(k) sales or sales support experience

  • Knowledge of qualified retirement plan and group benefit insurance products

  • Familiarity with retirement plan investment principles

  • Proficient with working in Microsoft Power Point and Excel

  • Industry coursework such as CPFA, QPFC, QKA, ARPC, AIF, AIFA, CIMA or CFP beneficial

  • Highly effective interpersonal, communication, and presentation skills

  • Strong analytical ability to identify and introduce efficient workflow methods

What You’ll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday in office.

  • Generous Paid-Time Off plan for you to enjoy time out of the office.

  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.

  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.

  • Extensive Work-Life Resources to lend a helping hand.

  • Sentry Foundation gift matching program to encourage charitable giving.

  • Continue your education and career development through Sentry University (SentryU).

About Sentry

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Casey Van Der Geest

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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