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

Outside Sales Representative and Trainer

$85k - $105k

Cleft of the Rock, Inc.

Job Description

Job Description

Outside Sales Representative & Trainer

About Us

At Cleft of the Rock , we believe in serving people first. We help businesses and individuals protect what matters most through supplemental insurance solutions but our real mission is to care for others and provide peace of mind . Our culture is built on compassion, connection, and purpose.

Your Role

As an Outside Sales Representative & Trainer , you'll do more than sell you'll serve. You'll connect with local business owners, listen to their needs, and help them find insurance solutions that make a real difference. Along the way, you'll also train and mentor others, using your natural warmth and people skills to help your team grow and succeed.

Key Responsibilities:

  • Build meaningful relationships with business owners, managers, and employees

  • Present supplemental insurance solutions that align with client needs

  • Conduct group presentations and one-on-one consultations

  • Train and support new team members, helping them build confidence and success

  • Follow up with clients regularly to ensure satisfaction and continued support

  • Work closely with your manager to set goals and grow your impact in the field

What We Offer

  • Comprehensive training and mentorship to help you thrive

  • Weekly draw pay plus commissions and bonuses

  • Incentive programs including cash rewards, recognition, and travel opportunities

  • Opportunities for professional growth and leadership development

  • A supportive, mission-driven team environment centered on people and purpose

Who You Are

  • Compassionate, service-minded, and genuinely care about helping others

  • Skilled at building trust and creating lasting relationships

  • Encouraging and supportive a natural mentor and team player

  • Positive, motivated, and driven by making a meaningful impact

  • Licensed in Health & Life or willing to obtain a license (licensing assistance and reimbursement provided)

Company: Cleft of the Rock
Compensation: $85,000 - $105,000 per year with draw pay, commissions, and bonuses
Schedule: MondayFriday, weekends as needed
Location: In-person, business-to-business and individual sales

Join Us

If you're looking for a career where you can build relationships, serve others, and make a lasting impact , Cleft of the Rock offers the environment, training, and purpose to help you succeed as an Outside Sales Representative & Trainer .

Learn more:

Vacancy posted 23 days ago
Similar jobs that could be interesting for youBased on the Outside Sales Representative and Trainer in Richmond, KY vacancy
  • $87k - $107k

     ...Outside Sales Representative Are you looking for an Outside Sales position with unlimited earning potential in a flourishing industry? Are you looking for an opportunity where you can earn uncapped commissions while still having a base salary with full benefits? Have... 
    Suggested
    Work at office
    Immediate start
    Home office

    Hibu

    Richmond, KY
    1 day ago
  • A leading electrical contracting firm in Kentucky is seeking a Journeyman Electrician 1 to lead electrical installations and repairs. Qualified candidates will have 5-7 years of experience in commercial and industrial environments and must possess a strong ability to guide...
    Suggested

    Comfort Systems USA

    Richmond, KY
    2 days ago
  • $18 - $23 per hour

    Job Description Job Description Are you passionate about soccer and working with children? If so, we have an exciting opportunity for you to join our team at Super Soccer Stars as a Soccer Stars Coach! In this role, you will lead our children in fun and educational...
    Suggested
    Flexible hours
    Weekend work
    Day shift

    Super Soccer Stars

    Richmond, KY
    23 days ago
  • $85k - $105k

     ...Job Description Job Description Sales Representative & Trainer Serve, Mentor, and Make an Impact Company: Compass Business Group Pay: $85,000$105,000 per year (draw pay, commissions, bonuses) Schedule: MondayFriday, weekends as needed Location: In-person... 
    Suggested
    Weekly pay
    Local area
    Weekend work

    The Compass Business Group

    Berea, KY
    17 days ago
  •  ...to: * Lead the daily operations of 6-8 restaurants * Train, develop and supervise 5-8 Restaurant General Managers * Drive top-line Sales & Traffic growth in your Area * Deliver Financial Results by controlling COS, COL, and Semi-Variable Costs * Ensure Operational Excellence... 
    Suggested
    Shift work

    Pizza Hut

    Richmond, KY
    4 days ago
  • $85k - $105k

     ...Job Description Job Description Sales Representative & Trainer Leadership Opportunity (In-Person | Local Territory) Company: Compass Business Group Compensation: $85,000$105,000 per year (Draw Pay + Commission + Bonuses) Schedule: MondayFriday (occasional... 
    Weekly pay
    Full time
    For contractors
    Local area
    Immediate start

    The Compass Business Group

    Berea, KY
    23 days ago
  • $60k - $93k

    Cellular Sales Cellular Sales is Growing! Average and High-End Sales Consultants earn $60,000 - $93,000 +/ year Are you determined...  ...and inclusion. Are you ready to take control of your income and represent the best? We’re Verizon’s premier retail partner and have... 
    Local area

    Cellular Sales

    Richmond, KY
    2 days ago
  • Certified Nursing Assistant (CNA) – Medical Explorers Ignite Academy **2026 Ignite Academy Graduates Apply Here** This posting is intended to collect applications from 2026 graduates of the Medical Explorers Academy and share qualified candidates with department leaders...

    Baptist Health

    Richmond, KY
    1 day ago
  •  ...Job Description Vector Marketing has immediate openings for sales rep positions, start work within the week! Basic Responsibilities...  ...sales performance — not length of service or annual resets. Representatives are paid a base (24.00 base-appt) or commission, whichever is... 
    Weekly pay
    Full time
    Part time
    Work experience placement
    Internship
    Work at office
    Immediate start
    Flexible hours

    Vector Marketing

    Richmond, KY
    21 days ago
  • $69k

     ...Job Description Job Description Remote Insurance Sales Representative | Flexible Schedule | Commission-Based This position offers flexible...  ...States or Canada We do not hire candidates residing outside North America Responsibilities Contact provided leads... 
    Remote job
    Work from home
    Flexible hours

    HMG Careers

    Richmond, KY
    more than 2 months ago
  • A leading electrical contracting firm is seeking a Journeyman Electrician 1 in Berea, Kentucky. You will oversee small teams, perform electrical installations and repairs, and mentor apprentices. The ideal candidate should have 5-7 years of hands-on experience in commercial...

    Comfort Systems USA

    Berea, KY
    3 days ago
  •  ...Loan Sales Specialist At OneMain, Loan Sales Specialists empower customers by listening to their needs and providing access to friendly, fast, and affordable financing for life's expenses. In this role, our team members thrive in a competitive atmosphere where hard... 
    Local area
    Monday to Friday

    Foursight Capital LLC

    Richmond, KY
    5 days ago
  •  ...Asia. We complement our extensive line of Motive Power and Energy Systems with a full range of integrated services and systems. With sales and service locations throughout the world, and over 100 years of battery experience, EnerSys is the power/full solution for stored... 
    Work at office
    Local area
    Worldwide

    EnerSys

    Richmond, KY
    1 day ago
  • $2,500 per week

     ...Job Description Job Description Life Insurance Sales Agent – Earn up to $2,500+ a week with Exclusive Leads! Contractor Dental, Medical $60,000 to $100,000 a year Earn what you’re worth and get paid in 24 hrs. No cold calling! We can help you get licensed... 
    Weekly pay
    For contractors
    Local area

    Lincoln Heritage Life Insurance Company

    Richmond, KY
    a month ago
  •  ...results, and integrity, offering a career where your efforts directly shape your success. Position Description: As a Direct Sales Representative, you'll take ownership of your territory by building relationships with business owners and individuals, understanding their... 
    For contractors
    Self employment

    Executive Financial Partners LLC

    Richmond, KY
    11 days ago
  • Job Description Job Description Brick/Block Laborer – Commercial Projects Year-Round Work | Lang Masonry Contractors About the Role: Lang Masonry Contractors is seeking construction Laborers for year-round commercial Masonry work throughout Ohio, West ...
    For contractors
    Flexible hours

    Lang Masonry Contractors Inc

    Richmond, KY
    20 days ago
  •  ...business owners to introduce supplemental health insurance options that provide meaningful financial protection. Learn simple, proven sales systems that build confidence quickly. Set personal goals, hit them, and move up based on performance—not tenure. What You... 
    Weekly pay

    Alpine Legacy Group

    Richmond, KY
    4 days ago
  •  ...Job Description Job Description Senior Sales Representative & Training Mentor at Alleviation – Lead, Inspire, Educate, and Succeed Alleviation: Cultivating Leadership and Expertise At Alleviation, we distinguish ourselves in the insurance industry by fostering... 
    Weekly pay
    Full time

    Alleviation Enterprise LLC

    Richmond, KY
    4 days ago
  • $65k - $85k

     ...Job Description Job Description Junior Sales Representative About Us At Cleft of the Rock , we believe business is about more than numbers it's about people. Our mission is to provide compassionate, thoughtful solutions that help both businesses and individuals... 
    Full time
    For contractors
    Local area
    Immediate start

    Cleft of the Rock, Inc.

    Richmond, KY
    7 days ago
  •  ...individuals who are eager to embark on a rewarding journey in the sales industry. This entry-level opportunity is perfect for those...  ...Overview: Step into the role of a territory-based sales representative, where you'll thrive in an environment focused on direct engagement... 
    Weekly pay
    Work experience placement
    Local area

    Alleviation Enterprise LLC

    Richmond, KY
    4 days ago
  •  ...your rural territory: prospect, present, and close new accounts Partner with our local team to ensure seamless service Report sales activity and territory trends to management via call planner In person visits to referral sources within the assigned territory... 
    Work at office
    Local area

    Rotech Healthcare Inc.

    Richmond, KY
    7 days ago
  • $65k - $85k

     ...Job Description Job Description Entry-Level Sales Representative Company: Compass Business Group Employment Type: Full-Time | Independent Contractor Industry: Supplemental Insurance | B2B / Direct Sales Compensation: Commission-Based (Average $65,000... 
    Full time
    For contractors
    Local area

    The Compass Business Group

    Berea, KY
    29 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Outside Sales Representative and Trainer. Be the first to apply!