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Entry Level Insurance Broker Jobs in Wisconsin (NOW HIRING)

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Compliance Analyst I

Milwaukee, WI · On-site +1

Compliance Analyst I Under general supervision, performs one or more entry-level compliance duties ... With a fervent focus on those it serves, including insurance brokers, consultants, third-party ...

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Compliance Analyst I

Milwaukee, WI · On-site

... more entry-level compliance duties on a professional level working with the VP of Compliance ... With a fervent focus on those it serves, including insurance brokers, consultants, third-party ...

Paramark Corp.

Associate Regional Manager

New Richmond, WI

$79K - $107K/yr

... brokerage services for private investors, institutions, corporations, not-for-profits, homeowner ... This is a developmental, entrylevel regional role designed to build leadership, budgeting, and ...

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Entry Level Insurance Broker information

See Wisconsin salary details

$39.4K

$88K

$120.1K

How much do entry level insurance broker jobs pay per year?

As of Jul 30, 2026, the average yearly pay for entry level insurance broker in Wisconsin is $88,039.00, according to ZipRecruiter salary data. Most workers in this role earn between $76,700.00 and $100,900.00 per year, depending on experience, location, and employer.

What is the difference between Entry Level Insurance Broker vs Insurance Agent?

AspectEntry Level Insurance BrokerInsurance Agent
CertificationsLicensing required, often entry-levelLicensing required, similar requirements
Work EnvironmentOffice, client meetings, independent workOffice, client interactions, agency setting
Industry UsageCommonly used for those starting in insurance sales and brokerageWidely used for sales and policy servicing roles

Both roles require licensing and involve client interactions, but insurance brokers often work independently to find policies across multiple providers, while insurance agents typically represent specific companies. The roles overlap in certifications and work environment, making them closely related but distinct in scope and independence.

How to become an independent Insurance Broker with no experience?

To become an independent insurance broker, you should start by obtaining the necessary state licensing by completing pre-licensing education and passing the licensing exam. Gaining knowledge of insurance products and sales techniques is essential, and building relationships with insurance carriers can help you access policies to sell. While experience is not mandatory, developing strong communication skills and understanding industry regulations are crucial for success in this role.

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

To thrive as an Entry Level Insurance Broker, you need a basic understanding of insurance products, sales principles, and often a relevant state-issued insurance license. Familiarity with CRM software, quoting tools, and underwriting systems is typically required. Strong interpersonal skills, active listening, and resilience help you build client relationships and handle rejections effectively. These skills are essential for building trust with clients, meeting sales targets, and ensuring regulatory compliance in a competitive industry.

Why do so many insurance agents quit?

Insurance agents often leave the profession due to high competition, inconsistent income, and the pressure to meet sales targets. The job requires strong interpersonal skills, self-motivation, and ongoing training, which can be challenging for some individuals to sustain over time.

How to qualify as an Insurance Broker?

To qualify as an entry-level insurance broker, candidates typically need a high school diploma or equivalent, complete pre-licensing education, and pass a licensing exam specific to their state or country. Some roles may require basic knowledge of insurance products, strong communication skills, and the ability to pass background checks; ongoing education or certifications can enhance career prospects.

What jobs pay 4000 a week without a degree?

Entry level insurance broker roles typically do not pay $4,000 a week initially, as earnings depend on commissions and sales performance. High-earning insurance brokers can reach that level with experience, strong client networks, and sales skills, often working in commission-based environments. Other high-paying jobs without a degree include sales positions, real estate agents, and certain entrepreneurial roles, but they usually require experience and skill development.

What are some of the main challenges faced by entry-level insurance brokers, and how can they overcome them?

Entry-level insurance brokers often face challenges such as building a client base from scratch, understanding complex insurance products, and meeting sales targets. To overcome these challenges, new brokers should actively seek mentorship from experienced colleagues, invest time in learning about different insurance products, and develop strong networking and communication skills. Regular training, persistence, and leveraging CRM tools can also help streamline client management and improve sales performance.

What does an Entry Level Insurance Broker do?

An Entry Level Insurance Broker helps clients find and purchase insurance policies that best fit their needs. They typically work under the supervision of experienced brokers, learning about different types of insurance such as life, health, auto, and property. Their daily tasks often include assessing client needs, researching policy options, preparing quotes, and assisting with paperwork. Entry level brokers also spend time building client relationships and learning sales strategies. This role is a stepping stone to more advanced positions within the insurance industry.
What are the most commonly searched types of Insurance Broker jobs in Wisconsin? The most popular types of Insurance Broker jobs in Wisconsin are:
What are popular job titles related to Entry Level Insurance Broker jobs in Wisconsin? For Entry Level Insurance Broker jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Entry Level Insurance Broker jobs in Wisconsin look for? The top searched job categories for Entry Level Insurance Broker jobs in Wisconsin are:
Entry Level Insurance Broker jobs near you
Infographic showing various Entry Level Insurance Broker job openings in Wisconsin as of July 2026, with employment types broken down into 10% Locum Tenens, 79% Full Time, 7% Part Time, 1% Temporary, and 3% Contract. Highlights an 78% Physical, 6% Hybrid, and 16% Remote job distribution, with an average salary of $88,039 per year, or $42.3 per hour.

Entry Level Sales Executive - Trucking

Cottingham & Butler

Madison, WI • On-site

Contractor

Re-posted 17 days ago

Cottingham & Butler rating

8.6

Company rating: 8.6 out of 10

Based on 15 frontline employees who took The Breakroom Quiz

89th of 299 rated insurance

Job description

This position requires a 10–12-week training session in Dubuque, IA initially. Housing would be supplied if needed.

Cottingham & Butler is actively looking for ambitious and driven entry-level Sales Executives at our Madison, Wisconsin location! Seeking all sales minded, soon-to-be college graduates, recent college graduates, or individuals with 1-3 years of sales experience who are motivated by financial rewards.

What You'll Get:

At Cottingham & Butler, we offer an exceptional sales career that opens the door to boundless opportunities and unlimited earning potential. You will be immersed in a dynamic environment surrounded by a team that is dedicated to equipping you for success. Through comprehensive training, unparalleled service support, unique resources, and the necessary tools, we ensure that you have everything you need to build a highly lucrative sales career.

Cottingham & Butler Transportation Group provides first-class insurance solutions to over 2,500 trucking companies across the U.S. Our service extends beyond buying insurance to helping our clients with safety, claims, and compliance challenges. As the leading insurance broker in the transportation industry, we provide better solutions, better advice, and better results.

What You'll Do:

  • Learn the business and become a trusted advisor to company leaders.
  • Identify, qualify, and close prospects.
  • Manage and retain your book of business and actively work towards its growth to unlock substantial financial growth.
  • Strategize and develop customized solutions for clients, leveraging available programs to deliver services that exceed client expectations.
  • Cultivate strong relationships with top decision makers, ensuring long-term client retention.
  • Collaborate with our service team to create compelling proposals and deliver impactful presentations to clients and prospects.
  • Earn relevant designations and stay up-to-date on continuing education credits provided by the company to enhance your professional growth and earning potential.

Here are a few things that set us apart:

  • Our Team. 300+ experienced professionals that specialize in the trucking industry and have the vision and expertise to help our clients clearly identify the risks they face and develop the necessary steps to mitigate or avoid them
  • Market Access. Our experience and reputation in the transportation industry give us the ability to secure the most competitive terms from the top insurance markets.
  • Our Solutions. We offer a full range of traditional and non-traditional insurance solutions, including in-house claims, safety management, and captive insurance services. We also offer an independent contractor platform and brokerage claims advocacy. The best part- the services aren't charged back to the producer.
  • Trucking Captives. We are the exclusive broker for 7 trucking captives, including the two largest in the world. There are over 245 captive members and a 99% retention rate in our captives.
  • Clients love us. They choose us because they see value in the services we offer and stay with us because we exceed their expectations. The Transportation Division has an average annual organic growth rate of 12.5% and our client retention is over 95%.

People We Hire:

If you thrive in a fast-paced, competitive environment and possess a relentless drive for success, Cottingham & Butler is the ideal place for you. You will be surrounded by industry-leading professionals, including several teammates who manage books of business exceeding $1 million. Additionally, you'll have access to our exceptional service teams and in-house specialists focused on account management, technology, compliance, analytics, client communications, and more—resources that will elevate your sales performance and financial success.

About Cottingham & Butler:

At Cottingham & Butler, we sell a promise to help our clients through life's toughest moments. To deliver on that promise, we aim to hire, train, and grow the best professionals in the industry. We look for people with an insatiable desire to succeed, are committed to growing, and thrive on challenges. Our culture is guided by the theme of "better every day" constantly pushing ourselves to be better than yesterday – that's who we are and what we believe in.

As an organization, we are tremendously optimistic about the future and have incredibly high expectations for our people and our performance. Our ability to grow as a company, fuels investments in new resources to better serve our clients and provide the amazing career opportunities our employees want and deserve. This is why we are a growth company and why we are committed to being better every day.

Want to learn more? Follow us on www.CottinghamButler.com | LinkedIn | Facebook

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