Entry Level Sales Representative
$65k - $85kCleft of the Rock, Inc.
Job Description
Job Description
Entry-Level Sales Representative
About Us
At Cleft of the Rock , we believe in standing firm in service, compassion, and integrity. Our mission is to help businesses and individuals protect what matters most — their people and their financial security. We provide supplemental insurance solutions that offer peace of mind during life’s unexpected moments.
Our team is made up of caring, driven individuals who find purpose in helping others. We’re not just here to sell — we’re here to serve.
What You’ll Do
As an Entry-Level Sales Representative , you’ll play a key role in bringing financial security and support to both businesses and individual clients. You’ll work directly with business owners, decision-makers, and individuals to educate them on benefits that help protect their teams, families, and themselves.
Responsibilities:
Build and maintain relationships with local businesses and individual clients.
Conduct needs-based consultations to identify coverage options.
Present and enroll clients in supplemental insurance programs.
Follow up with business owners and individuals to ensure continued satisfaction.
Participate in weekly trainings and development meetings to grow your skills.
What We Offer:
Comprehensive training and hands-on mentorship.
Licensing assistance and reimbursement to help you get started.
A supportive, service-oriented team culture.
Unlimited earning potential with commission-based pay (average $65,000–$85,000 annually for entry-level agents).
An optional base draw during your first 6 weeks to support your transition.
Who You Are:
You find fulfillment in helping others and making a difference.
You’re self-motivated , reliable , and enjoy working independently.
You communicate with warmth and professionalism.
You’re eager to learn , grow , and serve .
You thrive in face-to-face relationship-building environments.
Company: Cleft of the Rock
Employment Type: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B / Direct Sales
Compensation: Commission-Based (Average $65,000–$85,000 per year) — with an optional base draw available for the first 6 weeks to help you get started
Location: Local Territory (In-person)
Join Us
If you’re ready to start a career that blends purpose with opportunity — where your success is built on serving both businesses and individuals — we’d love to meet you.
Apply today and take the first step toward a meaningful career with Cleft of the Rock .
Learn more at:
- Job Description Job Description At Alpine Legacy Group, we don't just sell insurance — we protect families, build leaders, and help people grow into the best version of themselves. We're a high-performance team with a heart for service, a passion for winning, and a...Entry levelWeekly payLocal area
- ...Job Description Job Description Join Our Team at True North Group Position: Sales Representative, Entry-Level Number of Openings: 1 Territory Sales Position Available About Us At True North Group, we believe great careers are built on real relationships...Entry levelWeekly payLocal areaFlexible hours
- ...willingness to obtain (study materials and state fees provided) Bachelor's degree or 4+ years of professional experience (Relevant sales, leadership, or athletic experience considered) Compensation & Growth ~1099 independent contractor role (self-employed, not a W-...Entry levelFor contractorsSelf employment
- ...At OneMain, Loan Sales Specialists empower customers by listening... ...phone and online. At every level, we're committed to an inclusive... ..., New Grad, Newly Graduated, Entry level, Financial Sales,... ...Customer experience, Financial Representative, Credit, Leadership, Manager...Entry levelFull timeTraineeshipLocal areaMonday to Friday
OneMain Financial
Winchester, KY5 days ago - ...ambitious and self-disciplined individual who is eager to enter the dynamic and competitive field of sales. This position is designed for those at an entry level, and while prior sales experience is appreciated, it is not a requirement. We offer comprehensive and continuous...Entry levelWeekly payWork experience placementLocal area
- ...Summer Cashier, Entry Level (No Experience Needed) Be the friendly face at the checkout. What you'll do: • Serve customers and process payments (cash, card and mobile) • Handle simple returns and keep your till balanced • Keep the checkout tidy and help...Entry levelWeekly payTemporary workSummer workSeasonal work
Seasonal Staff Co.
Winchester, KY1 day ago $25 - $50 per hour
Role Overview TSA is accepting applications for Lead and Supervisory Transportation Security Officers at airports in Winchester. These roles are ideal for individuals looking to step into leadership positions within airport security operations. TSA provides training...Entry levelShift workNight shiftWeekend workAirport Security Careers
Winchester, KYmore than 2 months ago- ...Job Description Job Description Summit is searching for an exceptional individual to join our team in an Entry Level Direct Sales position, tailored specifically for those with a background in retail or transitioning from the military. We recognize the value of your...Entry levelWeekly pay
$1,700 - $1,800 per week
...Preferred • Must Meet DOT Requirements Apply today and drive with a company built around safety, respect, and consistency. ENTRY LEVEL JOB: START YOUR CDL CAREER | OTR CDL-A DRIVER TRAINING PATH GET PAID TO LEARN | HOME BACK TO TEXAS | CORE48 DRIVER...Entry levelWeekly payFlexible hoursShift workCORE48 Transport
Winchester, KY17 days ago- ...Summer Cashier, Entry Level (No Experience Needed) Be the friendly face at the checkout. What you'll do: • Serve customers and process payments (cash, card and mobile) • Handle simple returns and keep your till balanced • Keep the checkout tidy and help on...Entry levelWeekly payTemporary workSummer workSeasonal 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 level
Dreambound
Winchester, KY2 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 levelFlexible hours
Dreambound
Winchester, KY3 days ago - ...Assisting customers Operating cash register Restocking merchandise REQUIREMENTS: This is an entry level role. No experience required! Whether you've worked as a retail sales associate, a gas station attendant or if this is your first job, apply today! ~ Must be 18+...Entry levelDaily paidPart timeLocal areaImmediate startShift work
$69k
...Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely, serving clients by providing guidance and protection solutions...Remote workWork from homeFlexible hoursHMG Careers
Winchester, KY15 hours 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 levelHourly payFlexible hoursCircle K
Winchester, KY3 days ago- ...the healthcare industry? Use Dreambound to find a Medical Billing and Coding program that will prepare you for this high-demand, entry-level role. What does a Medical Billing and Coding Specialist do? A medical billing and coding specialist processes and codes healthcare...Entry level
Dreambound
Winchester, KY2 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 timePart timeRemote workFocus Group Panel
Winchester, KY10 hours ago$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 levelHourly payWeekly payExtra incomeTemporary workPart timeFor contractorsSeasonal workRemote workWork from homeFlexible hoursOnline Consumer Panels America
Winchester, KY4 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 timePart timeRemote workFocus Group Panel
Winchester, KY10 hours 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 what you join. Works around any shift schedule....Remote workShift workMaxion Research
Winchester, KY3 days ago- ...Direct Sales Representative Summit Business Group is a rapidly growing insurance agency committed to providing outstanding supplemental benefits plans to small and medium-sized businesses and their employees. With a focus on excellence and leadership, we are seeking...Weekly payWork experience placementWork at office
- ..., Disability insurance, Flexible spending account, Health insurance, Life insurance, Paid time off, Vision insurance Seniority level: Entry level Employment type: Full-time Job function: Accounting/Auditing and Finance Industry: Civil Engineering Referrals increase...Entry levelFull timePart timeFlexible hours
$15 per hour
...Job Description Job Description Production Associates Needed – Winchester, KY Now Hiring! Looking for a great entry-level opportunity? We're hiring Production Associates in Winchester, KY! Schedule ~ Monday–Friday ~5:00 AM – 3:30 PM ~ Overtime required...Entry levelImmediate startMonday to FridayShift workDay shiftPeople Plus, Inc.
Winchester, KY19 days ago- Join to apply for the Store Crew role at 7-Eleven Crew positions are entry level opportunities with both full and part time possibilities to fit your schedule. As one would expect, cash handling, fuel transactions, cleaning, and stocking are part of the role with some foodservice...Entry levelFull timePart time
$25 - $29 per hour
...the job poster from Acro Service Corp Schedule Onsite | Sunday-Thursday | 11:00 PM - 7:30 AM Job Summary The QC Analyst is an entry‑level, hands‑on laboratory position responsible for performing routine and critical analytical testing to support quality control operations...Entry levelContract workTemporary work- Job Description A QC Analyst is an entry level position for individuals who use their understanding of science to perform the basic and critical experimental work of day-to-day analysis, including generation and analysis of data. Their work is “hands on” in an analytical...Entry levelWork experience placementInternship
- Our agency is seeking to fill an entry-level outside sales role in a new territory. The primary responsibility of this position will be developing a new book of business through making in person sales calls to businesses with a focus on new client acquisition and retention...Entry levelWeekly payWork experience placementLocal area
- ...possibilities by adding this side gig or growing a new career at Jackson Hewitt and apply today! If you join our team as a Seasonal Entry Level Tax Preparer , you'll conduct one-on-one tax interviews with clients, start to develop your book of business, and provide...Entry levelFull timePart timeSecond jobSeasonal workRelocation packageFlexible hoursShift work
Jackson Hewitt - DHI
Winchester, KY17 days ago $23 - $27 per hour
...KY 40391 Duration: 6 Months ONSITE POSITION - SHIFT - FRI, SAT, SUN & MON 6AM - 6PM. Description/Comment: A QC Analyst is an entry level position for individuals who use their understanding of science to perform the basic and critical experimental work of day-to-day...Entry levelContract workWork experience placementWork at officeShift work$29.09 per hour
...Position Summary A QC Analyst is an entry level position for individuals who use their understanding of science to perform the basic and critical experimental work of day-to-day analysis, including generation and analysis of data. Their work is hands on in an analytical...Entry levelHourly payContract workWork experience placementWork at officeLocal areaFlexible hoursAditi Consulting
Winchester, KY4 days ago
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Entry Level Sales Representative. Be the first to apply!
- respiratory sales specialist Winchester, KY
- sales representative flooring Winchester, KY
- customer service inside sales representative Winchester, KY
- sales representatives wanted Winchester, KY
- sales specialist Winchester, KY
- sales executive Winchester, KY
- new home sales consultant Winchester, KY
- roofing sales representative Winchester, KY
- group sales representative Winchester, KY
- sales specialist flooring Winchester, KY