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Entry Level Life Insurance Jobs in Madison, WI (NOW HIRING)

Istate Truck Center

Entry Level Diesel Mechanic

Windsor, WI

$25.25 - $33.25/hr

Job Title: Entry-Level Diesel Mechanic Location: Madison, Wisconsin Company: I-State Truck Center I ... Company-paid life insurance * Healthiest You virtual healthcare * PPE reimbursement (safety glasses ...

Istate Truck Center

Entry Level Diesel Mechanic

Windsor, WI · On-site

$25.25 - $33.25/hr

Job Title: Entry-Level Diesel Mechanic Location: Madison, Wisconsin Company: I-State Truck Center I ... Company-paid life insurance * Healthiest You virtual healthcare * PPE reimbursement (safety glasses ...

Istate Truck Center

Entry Level Diesel Mechanic

Windsor, WI · On-site

$25.25 - $33.25/hr

Job Title: Entry-Level Diesel Mechanic Location: Madison, Wisconsin Company: I-State Truck Center I ... Company-paid life insurance * Healthiest You virtual healthcare * PPE reimbursement (safety glasses ...

Kleinschmidt

Entry-Level Structural Engineer

Madison, WI · Hybrid

$65K - $86K/yr

Company Paid Short-Term Disability and Life Insurance * Paid Parental Leave * Tuition Assistance * Employee Ownership Kleinschmidt is an Equal Opportunity and Affirmative Action employer. It is our ...

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All JobsLife Insurance JobsEntry Level Life Insurance JobsEntry Level Life Insurance Jobs in Madison, WI

Entry Level Life Insurance information

See Madison, WI salary details

$30.7K

$88.8K

$132.5K

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

As of Aug 15, 2026, the average yearly pay for entry level life insurance in Madison, WI is $88,787.00, according to ZipRecruiter salary data. Most workers in this role earn between $73,100.00 and $100,800.00 per year, depending on experience, location, and employer.

What is an entry level life insurance?

An Entry Level Life Insurance job typically involves helping clients understand and purchase life insurance policies. Responsibilities may include generating leads, explaining coverage options, and processing applications. Most positions require strong communication skills and a willingness to learn about insurance products. Some roles offer training and licensing support. This is a great starting point for a career in the insurance industry.

What does an entry level life insurance do?

A typical day for an Entry Level Life Insurance agent often involves reaching out to prospective clients, scheduling consultations, and meeting with individuals or families to assess their insurance needs. You’ll also spend time preparing quotes, completing applications, and following up on leads, either independently or as part of a team. Many agents participate in team meetings for training, role-playing sales scenarios, and staying updated on policy changes. The work environment is usually a mix of office-based tasks and fieldwork, offering variety and opportunities to develop valuable sales and customer service skills.

How to start a career in entry level life insurance?

To start a career in entry level life insurance, obtain a state insurance license by completing pre-licensing education and passing the licensing exam. Entry-level roles often require strong communication skills, basic sales abilities, and knowledge of insurance products, with employers providing on-the-job training. Gaining relevant certifications or licenses can improve job prospects and advancement opportunities.

What are the key skills and qualifications needed to thrive in an entry level life insurance position?

To thrive as an Entry Level Life Insurance agent, you need strong interpersonal skills, basic knowledge of insurance products, and typically at least a high school diploma or equivalent. Familiarity with customer relationship management (CRM) software and the process for obtaining state life insurance licensing is also important. Outstanding communication, persistence, and the ability to build trust quickly are valuable soft skills for success in this field. These skills enable agents to effectively connect with clients, understand their needs, and provide the best insurance solutions in a competitive industry.

What are the most commonly searched types of Life Insurance jobs in Madison, WI?

The most popular types of Life Insurance jobs in Madison, WI are:

What are popular job titles related to Entry Level Life Insurance jobs in Madison, WI?

For Entry Level Life Insurance jobs in Madison, WI, the most frequently searched job titles are:

What job categories do people searching Entry Level Life Insurance jobs in Madison, WI look for?

The top searched job categories for Entry Level Life Insurance jobs in Madison, WI are:

What cities near Madison, WI are hiring for Entry Level Life Insurance jobs?

Cities near Madison, WI with the most Entry Level Life Insurance job openings:

Entry Level Life Insurance jobs near you
Infographic showing various Entry Level Life Insurance job openings in Madison, WI as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 28% Part Time, and 4% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $88,787 per year, or $42.7 per hour.

Entry-Level Outside Sales Representative -- Teachers, Coaches & Educators Welcome

The Impact Insurance Agency

Fort Atkinson, WI • On-site

$65K - $85K/yr

Full-time, Contractor

Medical, Life

Re-posted 25 days ago

Job description

Entry-Level Outside Sales Representative Teachers, Coaches & Educators Welcome

Company: Impact Insurance Agency
Pay: $65,000$85,000 average first-year income | Commission + Optional 6-Week Base Draw
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person

A Career Path for People Who Naturally Support Others

Many educators and coaches reach a moment where they want to keep helping people grow just in a new environment that offers flexibility, professional development, and long-term earning potential.

At Impact Insurance Agency, we partner with local businesses to provide supplemental insurance solutions that support employees and their families during life's unexpected moments. Teachers, mentors, and trainers often find this role to be a natural extension of what they already do best: building trust, encouraging others, and guiding meaningful conversations.

If you're someone who leads with empathy, enjoys connecting with people, and finds purpose in helping others succeed, this opportunity offers a rewarding next chapter.

The Opportunity

This entry-level outside sales role blends education, relationship-building, and ongoing client support. You'll meet face-to-face with business owners and employees, helping them understand benefit options in a way that feels clear, supportive, and approachable.

You don't need previous sales experience. Our structured training program is designed specifically for individuals transitioning from education, coaching, or other service-driven roles.

As an independent contractor, you'll manage your own local territory while working within a collaborative environment that provides mentorship, guidance, and consistency.

What You'll Do

  • Build genuine relationships with local business owners and their teams

  • Lead enrollment-style conversations that feel educational rather than sales-driven

  • Listen carefully and offer thoughtful, people-focused solutions

  • Support onboarding, follow-ups, and long-term client relationships

  • Manage appointments, scheduling, and territory activity

  • Participate in weekly collaboration, coaching, and professional development

Training & Support

  • Step-by-step onboarding designed for educators transitioning careers

  • Hands-on field mentorship and real-world learning

  • Health & Life licensing assistance and reimbursement

  • Coaching focused on communication, leadership, and relationship-based service

  • A collaborative culture built on encouragement, not pressure

Compensation & Structure

  • Commission-based income with performance bonuses

  • Average first-year income: $65,000$85,000 (performance-based)

  • Optional 6-week base draw while building your client base

  • Flexible daytime schedule with autonomy over your territory

  • Advancement opportunities into mentoring, training, or leadership roles

Ideal Background

This opportunity may resonate with you if you:

  • Have experience as a teacher, coach, educator, trainer, or mentor

  • Enjoy helping people feel confident in their decisions

  • Communicate with warmth, patience, and professionalism

  • Thrive in relationship-driven environments

  • Value collaboration and meaningful impact in your work

  • Are willing to obtain a Health & Life Insurance license (support provided)

Why Impact Insurance Agency

Our culture is built around service, collaboration, and genuine encouragement. Many of our leaders started in entry-level roles and grew through mentorship, consistency, and a strong desire to help others succeed both clients and teammates alike.

Apply Today

If you're ready to take the communication and leadership skills you've built in education and apply them in a people-focused professional career, we'd love to connect.

https://www.theimpactinsuranceagency.com/