Entry-Level Outside Sales Representative
Hinsdale, 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
Hinsdale, 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
Hinsdale, IL ยท On-site
$65K - $85K/yr
Entry-Level Outside Sales Representative Company ... Impact Insurance Agency Schedule: Full-Time | Independent Contractor Industry: Supplemental ...
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Chicago, IL ยท On-site
$80K - $100K/yr
... insurance coverageProfessional License exam fee reimbursementBonus OpportunitiesSupport of professional organization membership and activitiesWork-life balance through a flexible, casual work ...
Quick apply
Chicago, IL ยท On-site
$80K - $100K/yr
... insurance coverageProfessional License exam fee reimbursementBonus OpportunitiesSupport of professional organization membership and activitiesWork-life balance through a flexible, casual work ...
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
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
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
Schaumburg, 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
Schaumburg, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Chicago, IL ยท Remote
$1.5K - $5.3K/wk
No prior experience in finance or insurance is required. We provide full training and licensing support. Why recent grads choose this over a traditional job Typical entry-level job $42K-$55K Fixed ...
Quick apply
Chicago, IL ยท Remote
$1.5K - $5.3K/wk
No prior experience in finance or insurance is required. We provide full training and licensing support. Why recent grads choose this over a traditional job Typical entry-level job $42K-$55K Fixed ...
Schaumburg, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Schaumburg, IL ยท On-site
$43K - $52K/yr
... entry level sales position and progressed through our training into management. We find that ... Health insurance
Chicago, IL ยท Remote
$3.5K - $5.5K/wk
... insurance coverage. There is no cold calling involved. What you'll be doing: * Following up with ... Learning and applying a proven sales system Who this is a great fit for: Entry-level candidates ...
Quick apply
Chicago, IL ยท Remote
$3.5K - $5.5K/wk
... insurance coverage. There is no cold calling involved. What you'll be doing: * Following up with ... Learning and applying a proven sales system Who this is a great fit for: Entry-level candidates ...
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 ...
Schaumburg, 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 ...
Schaumburg, 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 ...
$50K - $60K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Quick apply
$50K - $60K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Lombard, 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
Lombard, IL ยท On-site
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Schaumburg, 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 ...
Schaumburg, 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 ...
Schaumburg, 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
Schaumburg, IL ยท On-site
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Schaumburg, 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 ...
Schaumburg, 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 ...
Lombard, IL ยท On-site
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
Lombard, IL ยท On-site
$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
Naperville, IL ยท On-site
$43K - $52K/yr
... started in our entry level account manager position and progressed through our training into ... Health insurance
| 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.

$65K - $85K/yr
Full-time, Contractor
Medical, Life
Re-posted 28 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.