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Entry Level Insurance Sales Jobs in Wisconsin (NOW HIRING)

Schneider

Entry Level Recruiter

Green Bay, WI

$35K - $46K/yr

Associate degree in business administration, human resources, sales or related field. * 1-2 years ... Company paid life insurance. * 401(k) savings plan with company match. * Paid time off and paid ...

Schneider

Entry Level Recruiter

Green Bay, WI

$35K - $46K/yr

Associate degree in business administration, human resources, sales or related field. * 1-2 years ... Company paid life insurance. * 401(k) savings plan with company match. * Paid time off and paid ...

TDS Telecom

Entry Level Sales Representative

Wausau, WI · On-site

$100K/yr

At TDS Telecom , our Entry Level Sales Representatives are more than sellers-they're trusted ... Life Insurance * 401(k) Plan * Generous Vacation & Paid Sick Leave * Seven Paid National Holidays ...

TDS Telecom

Entry Level Sales Representative

Wausau, WI · On-site

$100K/yr

At TDS Telecom , our Entry Level Sales Representatives are more than sellers-they're trusted ... Life Insurance * 401(k) Plan * Generous Vacation & Paid Sick Leave * Seven Paid National Holidays ...

TDS Telecom

Entry Level Sales Representative

Wausau, WI · On-site

$100K/yr

At TDS Telecom , our Entry Level Sales Representatives are more than sellers--they're trusted ... Life Insurance * 401(k) Plan * Generous Vacation & Paid Sick Leave * Seven Paid National Holidays ...

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All JobsInsurance Sales JobsEntry Level Insurance Sales JobsEntry Level Insurance Sales Jobs in Wisconsin

Entry Level Insurance Sales information

See Wisconsin salary details

$22.2K

$45.5K

$65.6K

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

As of Aug 2, 2026, the average yearly pay for entry level insurance sales in Wisconsin is $45,467.00, according to ZipRecruiter salary data. Most workers in this role earn between $37,300.00 and $50,500.00 per year, depending on experience, location, and employer.

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

To thrive as an Entry Level Insurance Sales representative, you need a high school diploma (or equivalent), basic sales knowledge, and an active state insurance license. Familiarity with CRM software, sales tracking tools, and online quoting systems is often required. Strong interpersonal skills, resilience, and persuasive communication help build client relationships and overcome objections. These skills and qualities are essential for meeting sales targets, ensuring regulatory compliance, and providing excellent customer service.

Why do so many insurance agents quit?

Many insurance agents quit due to the high-pressure sales environment, inconsistent income, and the need for strong interpersonal skills. The job often involves commission-based pay, which can lead to financial instability, especially for new agents building their client base. Additionally, the job requires persistence and ongoing training to succeed in a competitive market.

What are entry level positions in insurance?

Entry level insurance sales positions typically involve selling insurance policies such as life, health, or auto insurance under the supervision of experienced agents. These roles often require strong communication skills, basic knowledge of insurance products, and may involve obtaining relevant licenses or certifications. They provide foundational experience for a career in insurance sales and customer service.

What are some common challenges faced by entry-level insurance sales professionals, and how can they be overcome?

Entry-level insurance sales professionals often encounter challenges such as building a client base from scratch, handling rejections, and staying motivated in a commission-driven environment. To overcome these, it's helpful to actively network, seek mentorship from experienced colleagues, and consistently follow up with leads. Developing strong product knowledge and refining communication skills also boost confidence and credibility with potential clients. Many organizations offer training and support to help new agents succeed, so taking advantage of these resources is key.

What are entry level insurance sales jobs?

Entry level insurance sales jobs are positions designed for individuals who are new to the insurance industry and have little to no prior experience in sales. These roles typically involve helping clients understand and purchase various types of insurance policies, such as auto, home, life, or health insurance. Employees receive training in sales techniques, product knowledge, and regulatory requirements. The goal is to build strong customer relationships, meet sales targets, and grow a client base while learning the fundamentals of the insurance business.

What jobs pay 4000 a week without a degree?

Entry-level insurance sales positions can potentially pay $4,000 or more per week through commissions, especially for top performers in high-value markets. Success in such roles typically requires strong sales skills, persistence, and knowledge of insurance products, with earnings often based on commissions rather than fixed salaries.

Is entry level insurance sales hard?

Entry level insurance sales can be challenging as it requires developing sales skills, understanding insurance products, and building client relationships. Success often depends on communication abilities, persistence, and gaining industry knowledge through training and certifications. The role typically involves a commission-based structure and a learning curve for new agents.

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

AspectEntry Level Insurance SalesInsurance Agent
Required CredentialsBasic licensing, sales trainingLicensing, certifications, ongoing education
Work EnvironmentOffice, remote, or field salesOffice, client meetings, fieldwork
Employer & Industry UsageInsurance companies, agenciesIndependent agents, agencies, companies
Search & Comparison IntentEntry-level roles, sales trainingExperienced sales, licensing, career growth

Entry Level Insurance Sales typically refers to individuals starting in sales roles with basic licensing and training, often working under supervision. Insurance Agents usually have more experience, licensing, and may operate independently or own agencies. While both roles involve selling insurance products, the key differences lie in experience, independence, and responsibilities.

What are the most commonly searched types of Insurance Sales jobs in Wisconsin? The most popular types of Insurance Sales jobs in Wisconsin are:
What are popular job titles related to Entry Level Insurance Sales jobs in Wisconsin? For Entry Level Insurance Sales jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Entry Level Insurance Sales jobs in Wisconsin look for? The top searched job categories for Entry Level Insurance Sales jobs in Wisconsin are:
What cities in Wisconsin are hiring for Entry Level Insurance Sales jobs? Cities in Wisconsin with the most Entry Level Insurance Sales job openings:
Entry Level Insurance Sales jobs near you
Infographic showing various Entry Level Insurance Sales job openings in Wisconsin as of July 2026, with employment types broken down into 84% Full Time, 12% Part Time, 1% Temporary, and 3% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $45,467 per year, or $21.9 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 7 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/