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Entry Level Insurance Sales Agent Jobs in Milwaukee, WI

HSA Bank

Insurance Sales Agent

Milwaukee, WI · On-site

$24 - $26/hr

The Individual Sales Agent is responsible for generating business through education, advisement ... Product Knowledge - Strong working knowledge of insurance products like Medicare Supplement ...

HSA Bank

Insurance Sales Agent

Milwaukee, WI · On-site

$24 - $26/hr

The Individual Sales Agent is responsible for generating business through education, advisement ... Product Knowledge - Strong working knowledge of insurance products like Medicare Supplement ...

HSA Bank

Insurance Sales Agent

Milwaukee, WI · Remote

$24 - $26/hr

The Individual Sales Agent is responsible for generating business through education, advisement ... Product Knowledge - Strong working knowledge of insurance products like Medicare Supplement ...

The Long Agency

Life Insurance Sales Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

As a Life Insurance Sales Agent with the Long Agency, you will work with individuals and families who have requested information about life insurance coverage. This is a consultative sales role ...

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All JobsInsurance Sales Agent JobsEntry Level Insurance Sales Agent JobsEntry Level Insurance Sales Agent Jobs in Milwaukee, WI

Entry Level Insurance Sales Agent information

See Milwaukee, WI salary details

$27.1K

$71.4K

$137.4K

How much do entry level insurance sales agent jobs pay per year?

As of Aug 23, 2026, the average yearly pay for entry level insurance sales agent in Milwaukee, WI is $71,389.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,800.00 and $88,200.00 per year, depending on experience, location, and employer.

What does an entry level insurance sales agent do?

An entry level insurance sales agent helps clients understand and purchase insurance policies that meet their needs. They typically contact potential customers, explain policy details, answer questions, and assist with application processes. Agents may sell various types of insurance, such as auto, home, health, or life, depending on their employer. They also help clients update policies and handle renewals, while learning sales techniques and industry regulations on the job.

What are the key skills and qualifications needed to thrive as an entry level insurance sales agent?

To thrive as an Entry Level Insurance Sales Agent, you need strong interpersonal skills, a basic understanding of insurance products, and often a state insurance license. Familiarity with CRM software, quoting tools, and online policy management systems is typically required. Outstanding communication, resilience, and the ability to build rapport with clients are soft skills that set top performers apart. These skills and qualifications are crucial for effectively generating leads, closing sales, and maintaining positive client relationships in a competitive market.

What are some common challenges faced by entry level insurance sales agents, and how can they overcome them?

Entry level insurance sales agents often face challenges such as building a client base from scratch, handling rejection, and learning complex products and regulations. Success in this role requires persistence, strong communication skills, and a willingness to continually improve product knowledge. Many agents find it helpful to leverage mentorship from experienced colleagues, attend regular training sessions, and use customer relationship management tools to track leads and follow up effectively. Over time, developing trust with clients and becoming familiar with sales techniques will help agents overcome initial hurdles and grow their careers.

What is the difference between Entry Level Insurance Sales Agent vs Insurance Producer?

AspectEntry Level Insurance Sales AgentInsurance Producer
Required CredentialsLicensing in specific states, basic sales trainingLicensing required, often more advanced certifications
Work EnvironmentOffice, remote, or in-field salesOffice-based or in-field sales, client meetings
Employer & Industry UsageInsurance agencies, brokerages, direct insurersInsurance agencies, independent agencies, brokerages
Search & Comparison IntentEntry level, beginner, sales rolesSales, licensing, insurance careers

In summary, an Entry Level Insurance Sales Agent typically requires basic licensing and training, focusing on entry-level sales roles within insurance companies or agencies. An Insurance Producer often has more advanced licensing and may handle more complex sales or client portfolios. Both roles are common in the insurance industry, but the Insurance Producer position generally involves greater responsibilities and experience.

How to be an entry level insurance sales agent with no experience?

To become an entry-level insurance sales agent with no experience, focus on obtaining a state license by completing pre-licensing courses and passing the licensing exam. Developing strong communication and sales skills, gaining product knowledge, and applying for trainee or entry-level positions can help start your career in insurance sales.

Is entry level insurance sales hard?

Entry level insurance sales can be challenging initially due to the need to learn product knowledge, develop sales skills, and build client relationships. Success often depends on communication abilities, persistence, and understanding of insurance policies, but many find it manageable with training and experience.

Why do so many entry level insurance sales agents quit?

Entry level insurance sales agents often quit due to the high rejection rate, inconsistent income, and the pressure to meet sales quotas. The job requires strong communication skills, self-motivation, and resilience, which can be challenging for new agents, leading to high turnover rates.

What are the most commonly searched types of Insurance Sales Agent jobs in Milwaukee, WI?

The most popular types of Insurance Sales Agent jobs in Milwaukee, WI are:

What are popular job titles related to Entry Level Insurance Sales Agent jobs in Milwaukee, WI?

For Entry Level Insurance Sales Agent jobs in Milwaukee, WI, the most frequently searched job titles are:

What job categories do people searching Entry Level Insurance Sales Agent jobs in Milwaukee, WI look for?

The top searched job categories for Entry Level Insurance Sales Agent jobs in Milwaukee, WI are:

What cities near Milwaukee, WI are hiring for Entry Level Insurance Sales Agent jobs?

Cities near Milwaukee, WI with the most Entry Level Insurance Sales Agent job openings:

Entry Level Insurance Sales Agent jobs near you
Infographic showing various Entry Level Insurance Sales Agent job openings in Milwaukee, WI as of August 2026, with employment types broken down into 100% Full Time. Highlights an 67% In-person, and 33% Hybrid job distribution, with an average salary of $71,389 per year, or $34.3 per hour.

Insurance Sales Agent

Rural Mutual Insurance - Badgerland

Racine, WI • On-site

Full-time

Posted 10 days ago

Job description

Description
Stop Climbing Someone Else's Ladder.
Build Something Meaningful.
You've developed skills that make a difference: building trust, leading under pressure, staying disciplined when things get hard, and showing up for the people counting on you.
Rural Mutual Insurance is looking for people who are ready to put those skills to work in a business they can grow and be proud of, in Racine and the surrounding communities.
Who Thrives Here
Insurance experience is valued but not required. Success in this role comes from the ability to build relationships, earn trust, stay organized, and serve others.
Many of our successful agents have backgrounds in:
  • Insurance and financial services
  • Military service, law enforcement, fire service, and emergency response
  • Education, coaching, and school administration
  • Community banking, mortgage lending, and agricultural finance
  • Small business ownership, contracting, and farm operations
  • Hospitality, retail management, and customer service leadership
  • Business development, account management, and professional sales
  • Healthcare, nonprofit leadership, and community organizations
  • Early-career professionals in business, agriculture, finance, communications, or related fields
  • If you've spent your career helping people, solving problems, leading teams, serving your community, or building relationships, you may already have the foundation to succeed. We'll provide the training, licensing support, and coaching to help you build the rest.

The Opportunity
As a Financed Agent with Rural Mutual Insurance, you will build and grow a book of business across Wisconsin. This is not a traditional sales job with a quota and a manager looking over your shoulder. It is an opportunity with structure, support, and a clear path to long-term growth.
What building your career looks like:
  • Develop relationships with individuals, families, farmers, and business owners
  • Identify customer risks and match them with the right insurance solutions
  • Build referral networks with local professionals, lenders, and community leaders
  • Participate in community organizations and local events
  • Create and execute a business plan with support from your manager
  • Grow a book of business that generates long-term, recurring revenue

Compensation and Growth
Financed Agents receive a base salary, commissions, and bonus opportunities. Starting salaries are typically around $48,000 annually. Total first-year earnings for agents who meet performance expectations generally range from $75,000 to $85,000, though actual earnings vary based on production and business results. As Financed Agents transition into Career Agent roles, income continues to grow through new business production and retention.
The financing model exists for a reason: it gives you the runway to build relationships the right way, without the pressure of needing to close a sale in week one. Your income grows as your business grows.
Agents who commit to the process and invest in their community see significant income growth in years two and three as referrals build, renewals compound, and their reputation takes hold.
Why Rural Mutual
Rural Mutual has served Wisconsin exclusively for more than 90 years. That singular focus is not a limitation. It is a competitive advantage.
It means:
  • Local underwriting decisions made by people who know Wisconsin
  • Deep credibility with the farming, small business, and rural communities you will serve
  • A trusted brand that opens doors in communities where reputation is everything
  • Commercial and farm product depth that creates real opportunity beyond personal lines

What we provide to set you up for success:
  • Comprehensive licensing support and pre-licensing training
  • Structured onboarding and a clearly defined ramp period
  • One-on-one coaching from an experienced manager
  • Marketing resources, tools, and ongoing development programs
  • Access to underwriting professionals who work alongside you
  • A community of agents across Wisconsin invested in each other's success

What It Takes to Succeed Here
Agents who are most successful in this role tend to be:
  • Driven by relationships, not transactions
  • Comfortable with accountability and honest about your performance
  • Active in your community or eager to become a recognized part of it
  • Resilient enough to keep going when the first month is harder than you expected
  • Forward-thinking enough to treat this like the business it is, not a job
  • Coachable enough to follow a proven system while it is still new to you

This is not the right fit if you are looking for a predictable routine, a capped salary, or a role where showing up is enough. The ceiling here is high, but so is the standard.
Ready to Build Something Meaningful?
If you have read this far and something feels familiar, that recognition is worth paying attention to.
We are building a team of agents across Wisconsin who are serious about serving their communities and building businesses they are proud of. If that is you, we want to talk.
Rural Mutual Insurance Company | Together We Keep Wisconsin Strong
Rural Mutual Insurance is proud to be an Equal Opportunity Employer. We are committed to creating an inclusive environment and welcome candidates of all backgrounds, experiences, and perspectives.
Responsibilities
• Cultivate and maintain strong relationships with clients, ensuring their insurance needs are met with personalized solutions.
• Identify potential risks for clients and recommend appropriate insurance products to safeguard their assets.
• Develop and implement a strategic business plan to grow a client base and achieve sales targets.
• Engage with local communities by participating in events and organizations to build a network of referrals.
• Collaborate with underwriting professionals to tailor insurance packages that align with client requirements.
• Provide exceptional customer service by promptly addressing inquiries and resolving any issues that arise.
• Stay informed about industry trends and product updates to offer clients the most current and relevant advice.
Qualifications
$46

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