Insurance Sales Agent Jobs in Madison, WI
Insurance Sales Agent jobs in Madison, Wisconsin are concentrated in the East Washington corridor, the West Side business parks near Mineral Point Road, and the Middleton area, with strong demand across health, property, and casualty lines at regional carriers and independent agencies. Employers hiring right now include American Family Insurance, COUNTRY Financial, and The Gainey Agency. See the openings below and apply to the ones that match your experience.
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At American Family, we're seeking highly motivated individuals with a demonstrated track record of success and eagerness to accomplish something that takes time, energy, and commitment. Do you possess a strong work ethic and have an inner drive that makes you hungry for success?
Insurance Agents operate as independent contractors, representing American Family and its products exclusively. As an insurance agent, you'll be responsible for your agency's overall management, sales, and growth. You'll also hire your team and work with them to meet the strategic business goals you set.
Reasons why you should become an American Family Insurance Agent:
- Financially Fit: American Family has the financial security to protect the dreams of your policy holders
- Fortune 500 company that is among the largest Property and Casualty insurance groups
- Offer American Family Insurance products as well as products and services through our subsidiary partners
- Training and support from a local team – from marketing, prospecting, business consultation and more
- Unlimited compensation potential including a New Agent Incentive Program
Requirements
o Obtain Property and Casualty and Life insurance licenses
o Ability to pass a motor vehicle, financial/credit and criminal background check
We believe people are an organization’s most valuable asset, and their ideas and experiences matter. From our CEO to our agency force, we’re committed to growing a diverse and inclusive culture that empowers innovation that will inspire, protect, and restore our customers’ dreams in ways never imagined.
At American Family, we're seeking highly motivated individuals with a demonstrated track record of success and eagerness to accomplish something that takes time, energy, and commitment. Do you possess a strong work ethic and have an inner drive that makes you hungry for success?
Insurance Agents operate as independent contractors, representing American Family and its products exclusively. As an insurance agent, you'll be responsible for your agency's overall management, sales, and growth. You'll also hire your team and work with them to meet the strategic business goals you set.
Reasons why you should become an American Family Insurance Agent:
- Financially Fit: American Family has the financial security to protect the dreams of your policy holders
- Fortune 500 company that is among the largest Property and Casualty insurance groups
- Offer American Family Insurance products as well as products and services through our subsidiary partners
- Training and support from a local team – from marketing, prospecting, business consultation and more
- Unlimited compensation potential including a New Agent Incentive Program
Requirements
o Obtain Property and Casualty and Life insurance licenses
o Ability to pass a motor vehicle, financial/credit and criminal background check
We believe people are an organization’s most valuable asset, and their ideas and experiences matter. From our CEO to our agency force, we’re committed to growing a diverse and inclusive culture that empowers innovation that will inspire, protect, and restore our customers’ dreams in ways never imagined.
See All 42 Insurance Sales Agent Jobs in Madison
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Find Insurance Sales Agent JobsInsurance Sales Agent Job Market in Madison
Who's Hiring
- American Family Insurance24
- COUNTRY Financial6
- The Gainey Agency6T
- Comparion Insurance Agency6
Top Industries Hiring
- Science & Research
Insurance Sales Agent Jobs in Madison: Frequently Asked Questions
How do I get an insurance sales agent job in Madison?
Focus your search on the regional carriers, independent agencies, and financial services firms concentrated along East Washington Avenue, the West Side business parks, and Middleton. Madison's large state-employee population and university community create steady demand for health and life products, so agents who can speak to group benefits and individual coverage stand out. Tailoring your outreach to locally rooted agencies rather than national chains tends to open doors faster in this market.
Which companies hire insurance sales agents in Madison?
Employers hiring insurance sales agents in Madison right now include American Family Insurance, COUNTRY Financial, and The Gainey Agency, based on current listings on Migrate Mate as of September 2026. Madison's market is a mix of regional mutual carriers, independent brokerages, and captive-agency operations that serve both the greater Dane County consumer base and the area's sizable employer groups.
Are there remote insurance sales agent jobs in Madison?
Yes, though remote availability is limited for client-facing sales roles that rely on in-person relationship building. About 100% of insurance sales agent openings tied to Madison are remote or hybrid as of September 2026, reflecting the hands-on nature of most sales positions. Where remote work does appear, it is most common in inside-sales or renewal-focused roles rather than new-business field positions.
How can I get an insurance sales agent job in Madison with little or no experience?
The most realistic entry path in Madison is through a captive-agency training program or a licensed customer service representative role at one of the regional carriers on the West Side or in Middleton, where structured onboarding is common. Independent agencies downtown often hire unlicensed candidates willing to obtain their property-casualty license quickly. Familiarity with the local market, including UW-Madison's student population and the large state-government workforce, is a practical differentiator for new agents here.
Which industries hire the most insurance sales agents in Madison?
The sectors hiring the most insurance sales agents in Madison are Science & Research, based on current listings on Migrate Mate as of September 2026. Madison's concentration of state institutions, a major research university, and a growing tech and finance sector creates layered demand for both commercial and personal lines coverage across those industries.
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