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

Cleek Financial

Be Seen First

Entry Level Insurance Sales Representative - No Cold Calling

Madison, WI · Remote

$85K - $125K/yr

Licensed Life/Health Agents Can Start Immediately * If Not Licensed- Great Training Program to ... Life Insurance License HUGE PLUS or Willingness To Obtain One * (Can Be Obtained In 20 Days Or Less)

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 ...

I-State 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 ...

AECOM

Entry-Level Traffic Engineer

Middleton, WI

Depending on your employment status, AECOM benefits may include medical, dental, vision, life, AD&D ... insurance, service recognition awards, retirement savings plan, and employee stock purchase plan.

New

AECOM

Entry-Level Traffic Engineer

Middleton, WI

Depending on your employment status, AECOM benefits may include medical, dental, vision, life, AD&D ... insurance, service recognition awards, retirement savings plan, and employee stock purchase plan.

New

AECOM

Entry-Level Traffic Engineer

Middleton, WI · On-site

Depending on your employment status, AECOM benefits may include medical, dental, vision, life, AD&D ... insurance, service recognition awards, retirement savings plan, and employee stock purchase plan.

New

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 ...

The Hearn Agency

Remote Mortgage Protection Agent

Mcfarland, WI · On-site +1

$1.5K - $1.7K/wk

Must have or be willing to obtain a life insurance license. Skills Required null More Details Employment Type: Full Time Location: Madison , Wisconsin , United States Experience Required: Entry Level ...

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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 27, 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.

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, 72% Full Time, 21% Part Time, and 6% Contract. Highlights an 90% Physical, 1% Hybrid, and 9% Remote job distribution, with an average salary of $88,787 per year, or $42.7 per hour.

Entry-Level Outside Sales Representative

The Impact Insurance Agency

Brodhead, WI • On-site

$65K - $85K/yr

Full-time, Contractor

Medical, Life

Re-posted 3 days ago

Job description

Entry-Level Outside Sales Representative

Company: Impact Insurance Agency
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person

A Career Path Built for Educators Who Love Helping People

Many teachers, coaches, and education professionals reach a point where they want to continue making a difference while also exploring new opportunities for growth, flexibility, and long-term income potential.

At Impact Insurance Agency, we partner with local businesses to provide supplemental insurance solutions that help employees and families feel supported during life's unexpected moments. Professionals from education often thrive here because the role draws on familiar strengths: communication, mentorship, leadership, and the ability to guide others through important decisions.

This isn't about leaving education behind it's about applying your experience in a new environment where your voice, structure, and people skills continue to matter.

The Opportunity

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

As an independent contractor, you'll manage your own local territory while working within a structured system that provides training, mentorship, and consistent support even if you've never worked in sales before.

What You'll Do

  • Connect with local businesses and introduce supplemental insurance solutions

  • Lead enrollment-style conversations that feel educational, not high-pressure

  • Break down complex information into clear, easy-to-understand guidance

  • Build long-term relationships through follow-up and consistent communication

  • Organize your schedule, appointments, and territory activity

  • Participate in weekly training, collaboration, and professional development

Training Designed for Education Professionals

  • Structured onboarding with step-by-step support

  • Hands-on field training and mentorship

  • Health & Life licensing assistance and reimbursement

  • Coaching focused on communication, leadership, and relationship skills

  • A collaborative team culture that values encouragement and growth

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

  • Long-term advancement into training, leadership, or mentoring roles

Ideal Background

This opportunity may resonate with you if you:

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

  • Enjoy presenting, guiding conversations, and helping people learn

  • Communicate with clarity, patience, and professionalism

  • Thrive in relationship-focused environments

  • Are looking for a career path that blends purpose with growth potential

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

Why Impact Insurance Agency

Our culture is built on mentorship, collaboration, and steady development. Many of our leaders began in entry-level roles and grew through consistency, encouragement, and a genuine desire to help others succeed. We believe strong relationships not pressure drive long-term success.

Apply Today

If you're ready to take your communication and leadership skills beyond the classroom and into a professional role where you can continue helping people every day, we'd love to connect.

https://www.theimpactinsuranceagency.com/