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Retired Insurance Jobs in Wisconsin (NOW HIRING)

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EXECUTIVE DIRECTOR VACANCY The Wisconsin Retired Educators' Association (WREA) Executive Council is ... insurance requirements for the WREA • review all contracts on an annual basis • oversee the ...

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EXECUTIVE DIRECTOR VACANCY The Wisconsin Retired Educators' Association (WREA) Executive Council is ... insurance requirements for the WREA • review all contracts on an annual basis • oversee the ...

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Within the campus, there is a non-regulated assisted living facility for retired nuns. The core ... Unencumbered driver's license and vehicle insurance. Company Description The School Sisters of St.

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

Self-managed with full-time effort required for success About AMBA For more than 65 years, AMBA has served retired public servants by providing access to supplemental insurance benefits not typically ...

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Showing results 1-20

Retired Insurance information

See Wisconsin salary details

$16K

$50.1K

$106.4K

How much do retired insurance jobs pay per year?

As of Jul 28, 2026, the average yearly pay for retired insurance in Wisconsin is $50,097.00, according to ZipRecruiter salary data. Most workers in this role earn between $30,133.00 and $58,440.00 per year, depending on experience, location, and employer.

Why do most insurance agents quit?

Most insurance agents quit due to high competition, fluctuating income, and the pressure to meet sales targets. The job often requires strong interpersonal skills, ongoing certifications, and a resilient attitude, which can lead to burnout and turnover.

What are some common post-retirement opportunities for professionals with experience in the insurance industry?

Many retired insurance professionals find rewarding opportunities in consulting, part-time advisory roles, or teaching insurance-related courses. Others choose to mentor younger agents or participate in industry associations, leveraging their expertise while enjoying greater flexibility. These roles often provide continued engagement with the industry without the demands of a full-time position, and can be a way to stay connected and share valuable knowledge.

What is a Retired Insurance job?

A Retired Insurance job typically refers to a retired insurance professional who may still provide consulting, advisory, or part-time services in the insurance industry. Some retired professionals assist clients with policy reviews, claims assistance, or compliance guidance. Others may work as independent contractors or mentors for younger insurance professionals. This type of work allows retired individuals to leverage their expertise while maintaining flexible schedules.

What is the best job for a retired person?

Retired insurance professionals often find success in part-time or consulting roles that utilize their industry knowledge, such as insurance agent, claims adjuster, or customer service representative. These jobs typically offer flexible schedules and require strong communication skills and familiarity with insurance policies and regulations.

What is the difference between Retired Insurance vs Insurance Agent?

AspectRetired InsuranceInsurance Agent
CredentialsTypically none, as they are no longer active in the industryLicenses and certifications required by state regulations
Work EnvironmentUsually inactive, may involve consulting or advisory roles post-retirementActive in selling policies, client meetings, and industry networking
Employer & Industry UsageRetired professionals, often independent or part-time rolesInsurance companies, agencies, or brokerages

Retired Insurance refers to individuals who have left active insurance work but may still engage in related activities, whereas Insurance Agents are actively selling and managing insurance policies. The main difference lies in their current work status and credentials, with retired individuals typically no longer holding active licenses, while agents are actively licensed and working in the field.

What is the best side hustle for retirees?

Retired insurance professionals often find success in side hustles such as consulting, freelance writing, or part-time customer service roles, leveraging their industry knowledge and communication skills. These jobs typically offer flexible schedules and require minimal additional training, making them suitable for retirees seeking supplemental income.

What jobs provide insurance after retirement?

Jobs such as full-time government employees, teachers, and certain unionized positions often offer retirement benefits including health insurance. Additionally, some large corporations and private sector roles may provide retiree health plans, especially if they have strong benefits packages or union representation. Part-time or self-employed roles typically do not include retirement insurance unless supplemented through private plans or personal savings.

What are the key skills and qualifications needed to thrive as an Insurance Agent, and why are they important?

To thrive as an Insurance Agent, you need a solid understanding of insurance products, risk assessment, sales techniques, and typically a state insurance license. Familiarity with customer relationship management (CRM) software, insurance quoting systems, and compliance platforms is important. Strong communication, negotiation, and problem-solving skills help build client trust and close sales. These skills and qualifications are crucial for meeting client needs, staying compliant, and achieving sales targets in a competitive industry.

What does it mean to be retired from an insurance career?

Being retired from an insurance career means that an individual has concluded their professional work in the insurance industry, either after reaching a certain age, fulfilling years of service, or choosing to leave the workforce. Retired insurance professionals may have worked in roles such as agents, underwriters, adjusters, or actuaries. Many retirees use their expertise for consulting, volunteering, or mentoring others in the field. Retirement allows them to enjoy benefits earned during their career, such as pensions or retirement savings. It also provides the opportunity to pursue personal interests and spend more time with family.
Infographic showing various Retired Insurance job openings in Wisconsin as of July 2026, with employment types broken down into 1% As Needed, 69% Full Time, 25% Part Time, and 5% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $50,097 per year, or $24.1 per hour.

Executive Director

Wisconsin Retired Educators Associa

Middleton, WI • On-site

Full-time

PTO

Posted 5 days ago

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Job description


EXECUTIVE DIRECTOR VACANCY


The Wisconsin Retired Educators’ Association (WREA) Executive Council is announcing a vacancy for

the position of Executive Director. The WREA is an issue-driven organization representing the

interests of Wisconsin’s retired educational community. The WREA Office is located in Middleton, WI

and serves the statewide membership of more than 6,000 retired educators.


The Executive Director reports to the Board of Directors and manages the affairs of the

Association, implements policies and directives of the Board, supervises and evaluates the work of

staff. The Executive Director develops and maintains relationships with affiliated local, state and

national organizations and also serves as a registered lobbyist for WREA.


Salary: Based on experience plus negotiated benefits.

Responsibilities of the Executive Director Includes:

• Assumes a leadership role in working with the President, Executive Council, Board of Directors

and WREA Foundation

trustees to promote the association’s purposes and goals and implements its policies and programs

• Coordinates lobbying efforts with the chair of the legislative committee and be a registered

lobbyist

• Serves as Team R.I.S.E. Committee chairperson per By-laws

• Manages the WREA office, including the employment of other staff

• Assumes responsibility for communications and publications of WREA

• Implements the association’s financial policies and develops annual budget

• Manages the daily financial affairs of WREA

• Serves as an ex-officio member of the Executive Council, the Board of Directors, the WREA

Foundation, and WREA committees

Qualifications:

• Degree in Public Administration or Educational Administration field is preferred

• Understanding of the Wisconsin Retirement System

• Understanding the importance of Public Education in Wisconsin

• Ability to inspire and motivate staff, volunteers and community

• Understanding of nonprofit financial management

• Excellent written and verbal communication skills

• Ability to build and maintain strong relationships with the Board, staff, donors, and community

partners

Note: For more information about WREA, please visit our website at www.wrea.net.


Application Process

Application packet must include:

1. A cover letter indicating reasons for your interest in the position.

2. A resume which reflects your qualifications, experiences and skills for the position.

3. The names, street addresses, telephone numbers and email addresses of three references.


Application must be post marked or emailed by: August 31, 2026


Please note that given the anticipated interest in this position, the names of applicants may be

released at some time during the hiring process and there will be background checks. The WREA is an

equal opportunity employer and does not discriminate on the basis of sex, creed, color, national

origin, disability, age or sexual orientation.


WREA Executive Director Job Description

Office Administration:

• accountable to the WREA Board of Directors

• establish office hours in consultation with the WREA President

• oversee the WREA office as outlined in the WREA Policy Handbook

• negotiate contracts for equipment

• review insurance requirements for the WREA

• review all contracts on an annual basis

• oversee the purchase of capital equipment

• maintain confidentiality of membership records and other WREA business

• respond to member requests and complaints

• participate in Condo Association meetings and related Condo office issues

• proficient in Word, Excel, Outlook, Power Point and Cloud based document receptacle


Staff Supervision:

• abide by personnel policies approved by the WREA Board of Directors

• employ and terminate office staff as outlined in the WREA Policy Handbook

• supervise office staff

• conduct annual staff reviews


Fiscal Management:

• fiscally responsible to the WREA Board of Directors and the WREA Foundation Board of

Trustees

• oversee fiscal records, completion of Compilation Report, and the timely filing of all tax

reports

• work closely with the WREA’s banker, accountant and office staff in making financial

decisions for both the WREA and the WREA Foundation

• oversee and assure compliance with adopted budget

• make recommendations for financial adjustments as may be necessary

• primary responsibility in facilitating both the WREA and the WREA Foundation annual

compilation

Association Meetings and Goals:

• develop a marketing plan for the association

• assist in annual convention and delegate assembly planning

• assist with meeting arrangements, agenda and program development for district meetings

WREA Board Activities and Committees:

• assume a leadership role in working with the WREA President, the WREA Board of

Directors and Standing Committees to promote the WREA’s purpose, missions, goals

and to implement policies and programs

• accountable to the WREA President and the WREA Board of Directors

• collaborate with the Team R.I.S.E. Committee in recruiting, retaining and regaining

members

• assure agreements with member benefit partners are honored

• assist in agenda preparations

• assist committees in goal-making and review

• work with the WREA Board of Directors to develop policy

• responsible for membership records: posting of new members, dues payments and membership

status

Legislative Activity:

• lobby and prepare legislative testimony for hearings and attend hearings as needed

• register as a lobbyist for WREA

• assure that the WREA has liaisons to critical organizations, advocacy groups and agencies with

common legislative interests

• prepare legislative materials in coordination with the Legislative Committee

• prepare legislative alerts on behalf of the Legislative Committee and the WREA Board of

Directors

• collaborate with the contracted WREA Lobbyist and the Legislative Committee to develop the

survey for each biennial session

• oversee the development of biennial legislative goals and priorities

• meet regularly with SAA Board of Directors to determine legislative priorities

Communication Activity:

• oversee website updating

• communicate pertinent information to members as needed

• work in conjunction with member benefit partners on member communications

• resolve member benefit complaints

• develop resource materials as needed for association activities

• oversee the production of all association printed and electronic materials

• provide oversight and review of WREA communications and publications

• assist with Leadership News, Red Apple Express, Green Apple Express, WREA News email blasts, and

campaigns

• oversee the Retirement Seminars and distribution of promotional materials

Litigation (when involved):

• oversee litigation as directed by the WREA Board of Directors

• work with WREA attorney in the coordination and analysis of legal proceedings

Outreach Activity:

• represent the WREA in all external matters

• attend unit meetings as requested

• provide information of interest to retired and prospective members

• develop relationships with other agencies, organizations and coalitions

• monitor the Wisconsin Retirement System (WRS) and maintain contact with the Department of

Employee Trusts Funds (ETF) and the State of Wisconsin Investment Board (SWIB)

• develop and maintain relationships with state agencies and other public officials for the

association

• assist in tabulating convention and district meeting evaluations

Issues Analysis:

• study issues pertaining to the WREA goals and purposes

• initiate the development of organizational planning and activities regarding issues of critical

interest to the WREA including pension, education, health care reform and economic security


As an employee of WREA, the Executive Director will perform other duties as assigned by the WREA

President or Board of Directors.


Company Description

Check out the WREA website at wrea.net