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Insurance Agent Jobs in Oregon, WI (NOW HIRING)

The McCrimmon Agency

Life Insurance Agent

Madison, WI · On-site +1

$30K - $160K/yr

As a Life Insurance Agent with The McCrimmon Agency, you will: * Meet virtually with individuals and families to understand their financial protection needs * Educate clients on available insurance ...

Empire State Careers

Remote Insurance Agent

Madison, WI · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Lone Star Careers

Remote Insurance Agent

Madison, WI · Remote

$69K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

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All JobsInsurance Agent JobsInsurance Agent Jobs in Oregon, WI

Insurance Agent information

See Oregon, WI salary details

$24.5K

$63.8K

$119.3K

How much do insurance agent jobs pay per year?

As of Sep 2, 2026, the average yearly pay for insurance agent in Oregon, WI is $63,838.00, according to ZipRecruiter salary data. Most workers in this role earn between $43,700.00 and $75,600.00 per year, depending on experience, location, and employer.

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, sales techniques, and relevant regulations, often supported by a state insurance license. Familiarity with customer relationship management (CRM) software and quoting systems is typically required. Strong interpersonal skills, active listening, and persuasive communication help agents build trust and effectively address client needs. These competencies are vital for meeting sales targets, ensuring compliance, and maintaining long-term client relationships.

What are some common challenges insurance agents face when building their client base, and how can they overcome them?

Insurance Agents often encounter challenges such as establishing trust with new clients, differentiating themselves in a competitive market, and managing client rejections. To overcome these obstacles, agents typically focus on building strong relationships through personalized service, maintaining up-to-date product knowledge, and leveraging networking opportunities. Successful agents also use digital marketing tools and referrals to expand their reach and consistently follow up with prospects to nurture long-term relationships.

What is the difference between Insurance Agent vs Insurance Broker?

AspectInsurance AgentInsurance Broker
CredentialsLicensed to sell policies for specific insurance companiesLicensed to represent multiple insurance companies and offer a variety of policies
Work EnvironmentTypically employed by an insurance company or agencyWorks independently or for brokerage firms, representing multiple insurers
Employer & Industry UsageInsurance companies, agenciesBrokerage firms, independent agencies
Search & Comparison IntentLooking for agents to buy policies from specific insurersSeeking brokers who can compare policies across multiple insurers

While both Insurance Agents and Insurance Brokers assist clients with insurance policies, agents usually represent a single insurer, whereas brokers work independently to compare options across multiple companies. Understanding these differences helps you choose the right professional for your insurance needs.

Is an insurance agent a good career?

An insurance agent is a sales professional who helps clients select insurance policies and provides ongoing service. The career offers flexible hours, commission-based income, and requires strong communication and sales skills, with success often dependent on building a client base and obtaining relevant licenses. It can be a stable and rewarding career for those interested in finance and customer service.

Is it hard to make money as an insurance agent?

Making money as an insurance agent can vary based on experience, sales skills, and the ability to build a client base. Income often depends on commissions from policies sold, and success typically requires persistence, networking, and product knowledge. Some agents earn substantial income, while others may find it challenging initially.
More about Insurance Agent jobs

What job categories do people searching Insurance Agent jobs in Oregon, WI look for?

The top searched job categories for Insurance Agent jobs in Oregon, WI are:

What cities near Oregon, WI are hiring for Insurance Agent jobs?

Cities near Oregon, WI with the most Insurance Agent job openings:

Insurance Agent jobs near you
Infographic showing various Insurance Agent job openings in Oregon, WI as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 23% Part Time, and 6% Contract. Highlights an 84% Physical, 1% Hybrid, and 15% Remote job distribution, with an average salary of $63,838 per year, or $30.7 per hour.

Insurance Agent- Deerfield, WI

American Family Mutual Insurance Company Si

Deerfield, WI • On-site

Full-time

Re-posted 29 days ago

American Family Insurance rating

7.5

Company rating: 7.5 out of 10

Based on 136 frontline employees who took The Breakroom Quiz

225th of 315 rated insurance

Job description

Community leader. Protector of dreams. That's what makes an American Family Insurance Agency Owner. It's a highly rewarding opportunity that allows you to create financial stability while making a positive impact on our customers' lives. If you're looking for a chance to own your future - we're interested in you! Apply today.

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

  • Obtain Property and Casualty and Life insurance licenses
  • 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.

#LI-AH1

What American Family Insurance employees say

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