Outside Sales Representative Entry-Level
$65k - $85kThe Impact Insurance Agency
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 you've spent time in education or coaching, you already know how much heart, energy, and dedication it takes to guide others. Many of our representatives come from classrooms, athletic programs, and mentoring roles where they cared deeply about the people they served — but eventually started looking for a path that offered more flexibility, professional growth, and long-term earning potential.
This opportunity allows you to keep using your communication skills, leadership presence, and ability to connect with people — just in a setting where your schedule, growth, and results are more within your control.
What This Role Looks Like
Instead of lesson planning, grading, or navigating the changing demands of the education system, you'll spend your time meeting with local businesses and their teams, helping employees understand supplemental insurance options that provide real support during unexpected life events.
You won't be expected to know insurance on day one. Our training is designed specifically for individuals transitioning from teaching, coaching, and other service-focused careers.
As an independent contractor, you'll manage your own local territory with flexibility — while still having structured guidance, mentorship, and a proven system to follow.
Day-to-Day Responsibilities
Connect with local small and mid-sized businesses in your community
Lead clear, educational conversations about benefit options
Help employees enroll and answer follow-up questions
Maintain organized notes, scheduling, and client relationships
Attend weekly training and professional development meetings
Build long-term partnerships through trust and consistency
Training Designed for Career Changers
Step-by-step onboarding — no prior sales experience required
Field mentorship and real-world learning opportunities
Health & Life licensing support and reimbursement
Coaching focused on communication, leadership, and relationship-building
A collaborative team culture that values encouragement over pressure
Compensation & Flexibility
Commission-based earnings 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
Growth opportunities into mentoring, training, or leadership roles
This Could Be a Strong Fit If You…
Have experience as a teacher, coach, educator, mentor, or trainer
Enjoy guiding people and explaining complex ideas in simple ways
Want a sustainable pace while still making a meaningful impact
Communicate clearly and build trust naturally
Appreciate structure but also want autonomy in your workday
Are open to obtaining a Health & Life Insurance license (we help you through it)
About Impact Insurance Agency
We partner with local businesses to provide supplemental insurance solutions that help employees and their families feel supported when it matters most. Our culture emphasizes mentorship, collaboration, and steady growth — and many of our leaders began by transitioning from other people-focused careers.
Interested in Learning More?
If you're exploring what comes next after education and want a role where your people skills, leadership experience, and passion for helping others still matter — we'd love to connect.
$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 levelFull timeFor contractorsLocal areaFlexible 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$100k - $300k
...Sales Representative Sales Representative (25 Years Experience Required) $100K$300K+ | Pre-Qualified Appointments | Fast Track to Leadership... .../ finance High-ticket B2C roles This role is: Not entry-level Built for hungry, high-level performers Compensation &...Entry levelWeekly payFlexible hours- ...Elevate Your Career. Drive Luxury Sales. Build Your Legacy. At American... ...professionals who can match that level of sophistication. This isn't an entry-level opportunity. If you have a proven... ...performers. What You'll Do: Represent premium brands and products with...Entry levelFlexible hoursWeekend workAfternoon shift
$900 - $1,500 per week
...a leading energy company helping homeowners across the East Coast make the switch to clean, affordable energy. We're looking for entry-level candidates in Chicago who are ready to get out in the field, learn a real skill, and get paid every week for their effort. This isn...Entry levelWeekly payDaily paidImmediate startShift work- ...Job Description Junior Sales Representative – Sports-Minded\n Chicago, IL Full-Time Entry-Level \n Competitive? Goal-driven? Like seeing yourself improve? \n We're looking for people with that mindset to join an expanding face-to-face sales team in Chicago....Entry levelFull time
- Edge BioPharma, Inc. in the United States is seeking a Pharmaceutical Sales Representative for Primary Care to promote our innovative and clinically proven products. This entry-level role welcomes candidates with no pharma experience who want to launch a rewarding sales...Entry level
$85k - $125k
...includes clear in-office expectations, while providing an appropriate level of flexibility based on role-specific responsibilities and... ...statementsDesired Qualifications:Previously held an internship or entry-level role in financial servicesBachelor’s degree in accounting,...Entry levelPermanent employmentFull timeInternshipWork at officeFlexible hoursDay shift$52k - $56k
...Entry-Level Sales Representative Chats Cloud Cover is a dynamic and fast-growing solutions provider committed to delivering exceptional support and service to our partners. We take pride in fostering an environment where talent is recognized, ideas are valued, and...Entry levelFull time$20 per hour
...Our Client in downtown Chicago Willis Tower is hiring an Entry-Level Licensed Benefits Advisor to handle live inbound calls, assess needs, and enroll clients in Medicare plans. Training and licensing are provided. This in-office, full-time role offers base pay of $20.0...Entry levelHourly payFull timeWork at officeShift work$100k - $200k
Are you an experienced in-home sales professional who knows how to run appointments, build trust, and close? At Perma-Seal, we're looking... ...'s license and ability to travel locally This is not an entry-level role. We are looking for professionals who know how to run and...Entry level$171.6k - $338.3k
Position Summary Are you a sales professional with an... ...Develop and maintain executive-level relationships with OpenAI leaders... ...OpenAI executives, sales representatives, and channel leaders.Experience... ...development From entry-level employees to senior leaders...Entry levelLocal area$100.4k - $197.9k
...Are you a relationship-oriented sales professional with an entrepreneurial mindset... ...Established relationships with Databricks sales representatives, client executives, industry leaders,... ...Professional development From entry-level employees to senior leaders, we believe...Entry levelLocal area- Circle Health in the United States is seeking a Pharmaceutical Sales Representative (entry level or experienced) to promote our medicines and support healthcare professionals in patient care. You will operate in your own territory, build relationships with providers, and...Entry level
$171.6k - $338.3k
Position Summary Are you a Sales Executive (SE) that has an entrepreneurial spirit... ...and influence key decision-makers at all levels within the client organizationAssume... ...more. Professional development From entry-level employees to senior leaders, we believe...Entry levelLocal area$15 per hour
...Job Description Job Description Entry-Level Sales Specialist Customer-Focused | Performance-Driven | Career Growth Opportunity We are seeking an Entry-Level Sales Representative to join our growing team. This role centers on direct customer interaction, presenting...Entry levelBase plus commissionHourly payWeekly payFull time- Pharmaceutical Sales Representative (Specialty to entry level both available) Pharmaceutical Sales Rep Opening Summary: We are seeking driven, capable, vivacious as well as positive sales account reps to build out and lead the product launch of a few new and innovative...Entry levelLocal areaImmediate start
- Circle Health is seeking a Pharmaceutical Sales Representative (entry level or experienced) to join our national team in the United States. You will partner with health care professionals, manage your own territory, and drive sales growth while upholding high ethical standards...Entry level
- Paragon Pharma seeks an entry level or specialty Pharmaceutical Sales Rep to educate, promote and sell products to physicians and healthcare providers. You will manage a territory, build relationships and coordinate with management to achieve sales goals while adhering...Entry levelRemote job
- Circle Health is seeking a Pharmaceutical Sales Representative (entry level or experienced) to drive product adoption across an assigned territory within the United States. You will partner with healthcare professionals, act as a product expert, and advance patient therapy...Entry level
$2,000 per month
...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$6,000 per month
...Entry-Level Sales Representative – NEXT Door & Window **** $500 sign-on bonus after 90 days of employment Launch Your Sales Career — Earn $6,00... ...still learning the business ~ Fast-track into a full-time Outside Sales Representative role within 6–12 months ~ Receive...Entry levelHourly payFull timeTemporary workImmediate startRelocation package- ...stronger doctor-patient trust. The Role We’re looking for a Sales Specialist who thrives in a fast-paced environment and has... ...#HealthcareTech #StartupCareers #HiringNow #LoopedApp Seniority level Seniority level Entry level Employment type Employment type Full-time Job...Entry levelFull time
$171.6k - $338.3k
...Are you an enthusiastic, self-motivated, and energetic sales professional with demonstrated sales success and a passion for... ...communities. Learn more. Professional development From entry-level employees to senior leaders, we believe there’s always room to...Entry levelLocal area$171.6k - $338.3k
...seeking a high-performing Vice President, Sales Executive to drive growth of recurring revenue... ...solution selling, and executive-level relationship development across pharma and... ...more. Professional development From entry-level employees to senior leaders, we believe...Entry levelLocal area- ...that always delivers! Why Join Us? Sell essential, recession-resistant services Represent a trusted brand with high customer retention Be part of a supportive sales team that offers consistent 1:1 coaching, ongoing sales learning, and real growth...Entry levelRelocation package
- ...customer relationships while promoting partnerships. Ideal candidates should have relevant supply chain or sales experience and strong communication skills. This entry-level, full-time position offers competitive pay and benefits including medical coverage. Join a team...Entry levelFull time
- ...services. Currently, we are looking for the Sales Representative to join our team in East Dundee, IL to... ...negotiation skills. ● Advanced/native-level English proficiency for professional... ..., IL $70,000.00-$90,000.00 1 month ago Entry Level Account Manager - Schaumburg, IL...Entry levelFull timeWork at office
- ...through our own investments, commitments, and actions across areas that help drive positive outcomes for our communities. From entry-level employees to senior leaders, we believe there's always room to learn. We offer opportunities to build new skills, take on...Entry levelLocal area
$300k
...Overview Are you an experienced Sales Professional, Restaurant Manager, Culinary Manager... ...Career pathing opportunities for both entry level, and experienced individuals Opportunity... ...automatic matching Job Summary This is an outside sales position responsible for promoting...Entry levelRelocationWeekend workAfternoon shift
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Outside Sales Representative Entry-Level. Be the first to apply!
- hvac sales representative Bridgeview, IL
- sales executive Bridgeview, IL
- real estate sales consultant Bridgeview, IL
- sales consultant Bridgeview, IL
- new home sales consultant Bridgeview, IL
- roofing sales consultant Bridgeview, IL
- direct sales representative Bridgeview, IL
- field agent Bridgeview, IL
- inside sales rep Bridgeview, IL
- respiratory sales specialist Bridgeview, IL



