Entry-Level Outside Sales Representative
Lyons, IL ยท On-site
$65K - $85K/yr
Entry-Level Outside Sales Representative Company ... Impact Insurance Agency Schedule: Full-Time | Independent Contractor Industry: Supplemental ...
Quick apply
Lyons, IL ยท On-site
$65K - $85K/yr
Entry-Level Outside Sales Representative Company ... Impact Insurance Agency Schedule: Full-Time | Independent Contractor Industry: Supplemental ...
Quick apply
Lyons, IL ยท On-site
$65K - $85K/yr
Entry-Level Outside Sales Representative Company ... Impact Insurance Agency Schedule: Full-Time | Independent Contractor Industry: Supplemental ...
Crestwood, IL ยท On-site
$65K - $85K/yr
Entry-Level Outside Sales Representative Company ... Impact Insurance Agency Schedule: Full-Time | Independent Contractor Industry: Supplemental ...
Quick apply
Crestwood, IL ยท On-site
$65K - $85K/yr
Entry-Level Outside Sales Representative Company ... Impact Insurance Agency Schedule: Full-Time | Independent Contractor Industry: Supplemental ...
Chicago, IL ยท On-site
$45K - $54K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Quick apply
Chicago, IL ยท On-site
$45K - $54K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Chicago, IL ยท On-site
$45K - $54K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Chicago, IL ยท On-site
$45K - $54K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Naperville, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Naperville, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Hammond, IN ยท On-site +1
... Entry Level Sales Representative ... In this role, you will have the opportunity to learn and grow in the life insurance industry while ...
Hammond, IN ยท On-site +1
... Entry Level Sales Representative ... In this role, you will have the opportunity to learn and grow in the life insurance industry while ...
Naperville, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Quick apply
Naperville, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Highland, IN ยท On-site
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Highland, IN ยท On-site
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Highland, IN ยท On-site
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Highland, IN ยท On-site
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
$14.28 - $20/hr
This outlines an entry-level technician position at Thomas KIA of Highland, located in Highland ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Be Seen First
Chicago, IL ยท Remote
$60K - $80K/yr
Entry Level Sales Associate (Remote) Remote | Virginia, Illinois, California, Washington, or Canada ... Previous insurance or sales experience is not required. Important Location Requirement This remote ...
Quick apply
Be Seen First
Chicago, IL ยท Remote
$60K - $80K/yr
Entry Level Sales Associate (Remote) Remote | Virginia, Illinois, California, Washington, or Canada ... Previous insurance or sales experience is not required. Important Location Requirement This remote ...
Chicago, IL ยท On-site
$34K - $64K/yr
You manage insurance programs, execute policy changes, update client information, facilitate collaboration, and work with the servicing team. Our future colleague. We'd love to meet you if your ...
Chicago, IL ยท On-site
$34K - $64K/yr
You manage insurance programs, execute policy changes, update client information, facilitate collaboration, and work with the servicing team. Our future colleague. We'd love to meet you if your ...
Chicago, IL ยท On-site
$34K - $64K/yr
You manage insurance programs, execute policy changes, update client information, facilitate collaboration, and work with the servicing team. Our future colleague. We'd love to meet you if your ...
Chicago, IL ยท On-site
$34K - $64K/yr
You manage insurance programs, execute policy changes, update client information, facilitate collaboration, and work with the servicing team. Our future colleague. We'd love to meet you if your ...
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Naperville, IL ยท On-site
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Quick apply
Naperville, IL ยท On-site
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Highland, IN ยท On-site
This outlines an entry-level technician position at Thomas Dodge Chrysler Jeep of Highland, located ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Highland, IN ยท On-site
This outlines an entry-level technician position at Thomas Dodge Chrysler Jeep of Highland, located ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Highland, IN ยท On-site
This outlines an entry-level technician position at Thomas Dodge Chrysler Jeep of Highland, located ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
Highland, IN ยท On-site
This outlines an entry-level technician position at Thomas Dodge Chrysler Jeep of Highland, located ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
This outlines an entry-level technician position at Thomas Dodge Chrysler Jeep of Highland, located ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
This outlines an entry-level technician position at Thomas Dodge Chrysler Jeep of Highland, located ... Comprehensive benefits package: medical, dental, and vision insurance, paid time off, and growth ...
| Aspect | Entry Level Insurance | Insurance Agent |
|---|---|---|
| Required Credentials | High school diploma or equivalent; licensing varies by state | High school diploma; licensing required |
| Work Environment | Office settings, call centers, or remote | Office, client meetings, or remote |
| Employer & Industry Usage | Insurance companies, brokers, agencies | Insurance agencies, brokerages, direct sales |
| Common Search & Comparison | Often compared for entry-level roles in insurance | Related role with sales and client interaction focus |
Entry Level Insurance roles typically require basic licensing and serve as foundational positions in insurance companies or agencies. Insurance Agents, while also entry-level in many cases, focus more on client sales and service, often requiring licensing and direct interaction with clients. Both roles are essential for starting a career in insurance, but Insurance Agents usually involve more active sales and customer engagement.
The most popular types of Insurance jobs in Matteson, IL are:
Cities near Matteson, IL with the most Entry Level Insurance job openings:

$65K - $85K/yr
Full-time
Medical, Life
Re-posted 18 days ago
Company: Impact Insurance Agency
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person
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.
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.
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
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
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
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)
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.
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.