Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Entry-Level Outside Sales Representative

$65k - $85k

The Impact Insurance Agency

Job Description

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.

Vacancy posted 3 days ago
Similar jobs that could be interesting for youBased on the Entry-Level Outside Sales Representative in Crestwood, IL vacancy
  • $65k - $85k

     ...Job Description Job Description Teachers & Educators Ready for a Different Kind of Impact Outside Sales Representative Entry-Level Impact Insurance Agency | Full-Time | Independent Contractor | Local Territory Bring Your Experience Into a New Setting If... 
    Entry level
    Full time
    For contractors
    Local area
    Flexible hours

    The Impact Insurance Agency

    Posen, IL
    21 days ago
  • $65k - $85k

     ...Job Description 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... 
    Entry level
    Full time
    For contractors
    Local area
    Flexible hours

    The Impact Insurance Agency

    Crestwood, IL
    2 days ago
  • $120k - $250k

     ...two decades, is immediately hiring Outside Sales Representatives.   In this role, you will be the face...  ...mobile device for photos/notes/lead entries.  Location: South and Southwest Chicago...  ...this is the perfect career for entry level or experienced professionals looking... 
    Entry level
    Full time
    For contractors
    Work at office
    Local area
    Immediate start
    Day shift
    Afternoon shift

    AmeriPro Roofing

    Oak Lawn, IL
    27 days ago
  • $65k

     ...Description Turano Baking Company is expanding our National Sales team! We are seeking driven sales professionals -...  ...environment, we want to talk. We are hiring across experience levels: Entry-Level / Junior Sales (0-3 years) Starting at $65,000+ Ideal... 
    Entry level
    Full time
    Monday to Friday

    Turano Baking Company

    Berwyn, IL
    18 hours ago
  •  ...managers with a retail background to join our winning team! Job Summary: Junior Assistant Manager - This is our entry level management position, which will allow you to learn our business, while giving you the skills to operate one of our stores. At least... 
    Entry level

    Rainbow Shops

    Calumet City, IL
    18 hours ago
  •  ...Luxury Sales Professional 5+ Years' Experience Required At American Sale...  ...professionals who can match that level of sophistication. This isn't an entry-level opportunity. If you have a proven...  ...path. What You'll Do: Represent premium brands and products with confidence... 
    Entry level
    Flexible hours
    Weekend work
    Afternoon shift

    American Sale Corporation

    Bridgeview, IL
    5 days ago
  • $1,000 - $2,000 per week

     ...Sales Representative - Paid Training - $100K+ Yearly Earn Up to $1000+ Per Sale | Entry-Level Welcome | Uncapped Commission | Benefits Package Protect Families While Building a High-Income Career At Custom Home Security, a Brinks new homeowner division, we are... 
    Entry level
    Permanent employment
    Remote work

    Custom Home Security

    Alsip, IL
    6 days ago
  • $100k

     ...Description Job Description Are you ready to get outside and make great things happen? Do you have a...  ...If YES, keep reading about this full-time Sales Representative position with Legacy Restoration! We're hiring multiple entry-level representatives to join our team and help... 
    Entry level
    Full time
    Local area
    Monday to Friday

    Legacy Restoration LLC

    Tinley Park, IL
    21 days ago
  • $21 per hour

     ...Shift Lead – Car Wash Job Level: Entry-Level Leadership Location: Burbank, IL Status: Full-Time & Part-Time Compensation:...  ...the opportunity to earn commission on monthly wash membership sales. About Us: WashU Car Wash is a modern express car wash... 
    Entry level
    Hourly pay
    Full time
    Part time
    Flexible hours
    Shift work
    Weekend work

    Wash U Carwash

    Burbank, IL
    3 days ago
  •  ...path in the healthcare industry? Use Dreambound to find a Electrocardiogram program that will prepare you for this high-demand, entry-level role. What does an ECG / EKG Technician do? An ECG / EKG technician conducts diagnostic tests to measure and record the electrical... 
    Entry level
    Flexible hours

    Dreambound

    Chicago Ridge, IL
    1 day ago
  • Job Category : Sales Requisition Number : NEWCO003220 Posted: February...  ...accounts of all sizes by representing the S Mechanical externally...  ...with business leaders at all levels. 50% or more travel required...  ...all levels (C-level down to entry-level support roles). Ability... 
    Entry level
    Full time
    Immediate start

    Crete United

    Oak Forest, IL
    2 days ago
  • $72k - $130k

     ...Job Description Job Description $3,900 Sign-On Bonus* Entry Level Sales Representative Build Your Career With Purpose At POWER, sales is more than closing deals - it's about helping homeowners make confident decisions while building a career with unlimited... 
    Entry level
    Hourly pay
    Weekly pay
    Full time
    Work at office
    Relocation
    Relocation package

    Power Home Remodeling

    Oak Lawn, IL
    9 days ago
  •  ...About the Role We are looking for a motivated and detail-oriented Entry-Level Administrative Assistant to support our operations team. This role is ideal for someone eager to learn, grow within the company, and take on more responsibilities over time. The position... 
    Entry level
    Part time
    Work at office

    Pediatrics On Demand

    Oak Lawn, IL
    1 day ago
  • $13 - $16 per hour

     ...transactions, restocking shelves, preparing coffee and food items, and keeping the store clean and organized. Employees may also assist with fuel transactions and customer questions. This role is entry-level and offers flexible scheduling. Average pay: $13 - $16 per hour.
    Entry level
    Hourly pay
    Flexible hours

    Circle K

    Oak Forest, IL
    2 days ago
  •  ...Associate Primary Location: Illinois-Cook-Burbank-Burbank IL Work Locations: Burbank IL 7910 South Cicero Ave Ste 8004a Burbank 60459 Schedule: Regular Shift: Standard Employee Status: Entry Level Job Type: Part-time Job Level: Day Job Ross Stores
    Entry level
    Part time
    Shift work

    Ross Stores

    Burbank, IL
    4 days ago
  • $1,200 per week

     .../07/2026 Duration: 36 weeks Hours per week: 20 hours per week Shift: 8 hours, days Employment Type: Travel ID: 1794606 Seniority level Entry level Referrals increase your chances of interviewing at Aequor, Allied Division by 2x Get notified about new Speech Language Pathologist... 
    Entry level
    Shift work

    Aequor, Allied Division

    Oak Lawn, IL
    5 days ago
  • A leading memory care provider in Palos Heights, IL is seeking a full-time Life Enrichment Coordinator. This entry-level position involves planning and implementing recreational activities for residents, supporting their well-being through daily interaction, and ensuring... 
    Entry level
    Full time

    Arden Courts

    Palos Heights, IL
    1 day ago
  • $65k - $85k

     ...Job Description 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 |... 
    Entry level
    Full time
    For contractors
    Local area
    Flexible hours

    The Impact Insurance Agency

    Dolton, IL
    25 days ago
  • $790 per week

     ...internet connection. No degree, no résumé, no experience. Why Maxion Research: genuine paid studies with real companies — not a sales pitch or a "get rich" scheme. Your information stays private, and you choose which studies you join. Work it around a job, school,... 
    Remote work

    Maxion Research

    Oak Lawn, IL
    14 hours ago
  •  ...seeks a responsible individual for materials purchasing and vendor negotiation. The role requires a bachelor's degree and offers entry-level experience. The individual will evaluate vendor quotes and work under immediate supervision, ensuring adherence to guidelines. This... 
    Entry level
    Immediate start

    OLSA Resources, Inc.

    Alsip, IL
    1 day ago
  •  ...daily to support well-being. Coordinate with other staff for training and ensure a positive, stimulating environment. Seniority level Entry level Employment type Full-time Job function Management and Manufacturing Industries Hospitals and Health Care #J-18808-Ljbffr... 
    Entry level
    Full time

    Arden Courts

    Palos Heights, IL
    14 hours ago
  • $25 - $45 per hour

     ...participants are engaged and to achieve the representative sample needed. Participation in these...  ...recordings, videos, product journal entries, etc.) Take care of the product being tested...  ...perfect for those looking for an entry-level opportunity, flexible or seasonal work,... 
    Entry level
    Hourly pay
    Weekly pay
    Extra income
    Temporary work
    Part time
    For contractors
    Seasonal work
    Remote work
    Flexible hours

    GL1

    Crestwood, IL
    3 days ago
  •  ...their assets and promise a profound purpose: ensuring a brighter future for every client. Role Overview: As a Benefits Sales Representative, you play a pivotal role in helping families protect their assets and secure their futures. You'll be the face of our... 
    Entry level
    Full time
    Work at office
    Work from home
    Flexible hours

    The Radu Group

    Crestwood, IL
    26 days ago
  • $790 per week

     ...internet connection. No degree, no résumé, no experience. Why Maxion Research: genuine paid studies with real companies — not a sales pitch or a "get rich" scheme. Your information stays private, and you choose which studies you join. Work it around a job, school,... 
    Remote work

    Maxion Research

    Oak Lawn, IL
    14 hours ago
  •  ...caretaker to your wonderful client by integrating into their day-to-day, just as their familial loved one would have. We accept entry-level candidates, and you can build your schedule at European Service at Home. Benefits: Paid training Flexible scheduling... 
    Entry level
    Full time
    Work at office
    Immediate start
    Flexible hours

    European Service At Home

    Palos Hills, IL
    5 days ago
  • $25 - $45 per hour

     ...participants are engaged and to achieve the representative sample needed. Participation in these...  ...recordings, videos, product journal entries, etc.) Take care of the product being...  ...perfect for those looking for an entry-level opportunity, flexible or seasonal work,... 
    Entry level
    Hourly pay
    Weekly pay
    Extra income
    Temporary work
    Part time
    For contractors
    Seasonal work
    Remote work
    Work from home
    Flexible hours

    Great Lion Co

    Midlothian, IL
    3 days ago
  • $52 - $72 per hour

     ...geographic location and the candidate’s years of experience and/or skill level. We are accepting applications for this position until a final...  ..., visit our careers page. Employment Details Seniority level: Entry level Employment type: Part-time Job function: Health Care... 
    Entry level
    Part time
    Relief

    Marathon Health

    Crestwood, IL
    3 days ago
  • $790 per week

     ...reliable internet. No degree, no résumé, no experience. Why Focus Group Panel: real research with real brands — not a scam or a sales pitch. Your info stays private, and you choose what you join. Part-time or full-time, on your schedule. Pay: up to $790/week,... 
    Full time
    Part time
    Remote work

    Focus Group Panel

    Oak Lawn, IL
    3 days ago
  • $790 per week

     ...reliable internet. No degree, no résumé, no experience. Why Focus Group Panel: real studies with real brands — not a scam or a sales pitch. Your info stays private, and you choose what you join. Part-time or full-time, on your schedule. Pay: up to $790/week,... 
    Full time
    Part time
    Remote work

    Focus Group Panel

    Oak Lawn, IL
    14 hours ago
  •  ...see on the Soliant Health website. Chase Young Account Executive | Soliant Health (***) ***-**** ****@*****.*** Seniority level Entry level Employment type Full-time Job function Health Care Provider Industries: Hospitals and Health Care and Education #J-18808-Ljbffr... 
    Entry level
    Full time
    Immediate start

    Soliant

    Burbank, IL
    2 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Entry-Level Outside Sales Representative. Be the first to apply!