Entry-Level Outside Sales Representative
$65k - $85kThe 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
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 OpportunityThis 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 DoConnect 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.
Apply TodayIf 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.
- ...Job Description Job Description We're looking for a personable, motivated Entry-Level B2B Sales Representative to join our team at Treenova Inc. This is an entry-level field sales position designed for individuals who are starting their career in sales and want hands...Entry levelLocal area
- ...Vector Marketing has immediate openings for sales rep positions, start work within the... ...length of service or annual resets. Representatives are paid a base (25.00 base-appt) or commission... ...enjoyed working with people. This entry level sales position is a great fit for...Entry levelWeekly payFull timePart timeWork experience placementInternshipWork at officeImmediate startFlexible hours
$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 levelFull timeFor contractorsWork at officeLocal areaImmediate startDay shiftAfternoon shift$72k - $130k
...Job Description Job Description $3,900 Sign-on Bonus* Entry-Level Sales Representative Power is where hustle meets purpose. It’s where leadership opportunities, life-enhancing benefits, and award-winning culture come together. Why? Because our people are our most...Entry levelHourly payWeekly payFull timeWork at officeImmediate startRelocationRelocation package$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 levelFull timeFor contractorsLocal areaFlexible hours- ...Job Description Job Description We are a fast growing retail sales and brand consulting company in the Chicagoland area looking for an Entry Level Sales Representative to join our expanding team. Our company focuses on customer acquisition inside r etail environments...Entry level
- ...Description Job Description American Sale: “Elevate Your Career. Drive... ...professionals who can match that level of sophistication. This isn’t an entry-level opportunity. If you have a... ...performers. What You’ll Do: Represent premium brands and products with...Entry levelFlexible hoursWeekend workAfternoon shift
$80k
...TO SPEAK WITH A SEATING SPECIALIST TODAY! (***) ***-**** Why wait to earn more? Western Express has immediate openings for entry level company truck drivers and driver trainers. With our newly increased pay package, you'll earn one of the highest rates in the industry...Entry levelFull timeImmediate start$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 levelFull timeMonday to Friday- ...Territory Sales Representative – Entry Level / Part-Time (3 Days/Week) CHICAGO SOUTH Break Into Pharmaceutical Sales with Pivya® at ImpactBio... ...experience would be helpful, B2B sales, Pharma sales, outside sales, customer facing) • Strong interest in breaking...Entry levelFull timePart timeWork experience placementWork at office3 days per week
- A flexible remote work provider is seeking Remote Data Entry Research Panelists to participate in studies from the comfort of home. This position allows you to work part-time or full-time and offers comprehensive training. No prior experience is necessary but is welcome...Entry levelFull timePart timeRemote workFlexible hours
- ...A leading sales company is looking for individuals to join their remote sales team. This is a commission-based opportunity where entry-level applicants are welcome, and no degree is required. We seek motivated individuals with a strong work ethic who thrive in competitive...Entry levelHourly payRemote work
- ...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
$300k
...Sales Representative Sysco is the global leader in foodservice distribution. With over 71,000... ...Career pathing opportunities for both entry level, and experienced individuals Opportunity... ...matching Job Summary This is an outside sales position responsible for...Entry levelInternshipWorldwideRelocationWeekend workAfternoon shift$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 levelPermanent employmentRemote work- ...medical, dental, vision, disability and life insurance, sick pay, PTO/Vacation pay, paid holidays and retirement benefits (pension and/or 401(k) eligibility). This is an entry level position with advancement opportunity. Applications are accepted on an on-going basis.Entry levelWeekly payMinimum wageFull timePart timeLocal areaFlexible hours
- ...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 levelFlexible hours
- ...medical, dental, vision, disability and life insurance, sick pay, PTO/Vacation pay, paid holidays and retirement benefits (pension and/or 401(k) eligibility). This is an entry level position with advancement opportunity. Applications are accepted on an on-going basis.Entry levelMinimum wagePart timeLocal areaFlexible hours
$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 levelHourly payFlexible hours$16.4 - $17.75 per hour
...DESCRIPTION What is a Salesperson? Entry level sales position capable of supporting the DIY... ...work environment described here are representative of those that must be met by an... ...; however, they will occasionally be outside and exposed to various weather conditions...Entry levelFull timePart timeLocal areaShift workWeekend workAfternoon shift- ...working in varying work environments (freezer, refrigerator, sales floor, etc.) · Being a part of your community matters Why you... ...benefits (pension and/or 401(k) eligibility). This is an entry level position with advancement opportunity. Applications are accepted...Entry levelMinimum wagePart timeLocal areaFlexible hours
- ...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 levelImmediate start
- ...mind working in different environments (freezer, refrigerator, sales floor). · Being a part of your community matters. Why you... ...retirement benefits (pension and/or 401(k) eligibility). This is an entry level position with advancement opportunity. Applications are...Entry levelMinimum wageFull timeLocal areaFlexible hoursShift workNight shift
- ...Location: Illinois-Cook-Crestwood-Crestwood IL Work Locations: Crestwood IL 13200 S Cicero Ave Crestwood 60445 Schedule: Regular Shift: Standard Employee Status: Entry Level Job Type: Part-time Job Level: Day Job Job Posting: May 4, 2026 Ross StoresEntry levelPart timeShift work
- ...in the healthcare industry? Use Dreambound to find a Patient Care Technician program that will prepare you for this high-demand, entry-level role. What does a Patient Care Technician do? A patient care technician provides direct care to patients, assisting with daily...Entry levelFull time
- Jewel-Osco in Merrionette Park, Illinois, is looking for courtesy clerks, cashiers, or customer service associates. This role offers an opportunity to learn and grow while ensuring every customer's visit is memorable. Jewel-Osco values diversity and inclusion, and is committed...Entry levelWeekly payFlexible hours
$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- Jewel-Osco in Burbank, Illinois seeks enthusiastic courtesy clerks to elevate customer experiences. In this role, you will assist customers while fostering a sense of community and belonging. As part of a diverse and inclusive workforce, you’ll contribute to making every...Entry levelFlexible hours
- ...Entry Level Manager Culver's Hiring: Immediate Opening for a Highly Skilled Entry Level Manager Are you looking for a fun and loving work environment where your leadership truly makes a difference? Do you want to be part of a dynamic team that values enthusiasm and...Entry levelImmediate startShift work
- ...path in the business world? Use Dreambound to find a Business Administration program that will prepare you for this high-demand, entry-level role. What does a Business Administrator do? A business administrator supports the daily operations of an organization, coordinating...Entry levelFull timeWork at office
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Entry-Level Outside Sales Representative. Be the first to apply!
- sales management training program - entry level Crestwood, IL
- entry level management training Crestwood, IL
- entry level personal training Crestwood, IL
- sales Crestwood, IL
- life insurance sales Crestwood, IL
- online sales Crestwood, IL
- hvac service sales Crestwood, IL
- sales operations Crestwood, IL
- sales part time Crestwood, IL
- telephone sales Crestwood, IL




