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

Direct Sales Representative

Alpine Legacy Group

Job Description

Job Description

At Alpine Legacy Group, we don’t just talk about success — we build it. We protect families, develop leaders, and forge careers grounded in discipline, grit, and ownership. Every day, we show up ready to compete, raise the bar, and win as a team.

We’re expanding fast and looking for driven, competitive individuals who want more — more opportunity, more control, and more impact.

The Role

As a Direct Sales Representative, you’ll learn fast and earn faster. Our training is hands-on, built around real experience, mentorship, and accountability. You’ll gain the skills, mindset, and confidence to perform at a high level — while building something that lasts.

You’ll manage your local territory, offering our industry leading supplemental insurance programs — connecting with business owners, leading conversations, and helping families secure real protection for the unexpected.

What You’ll Do
  • Build and maintain strong relationships through direct meetings and networking.

  • Present, close, and deliver — from first handshake to lifelong client.

  • Use our CRM to manage your pipeline and drive results.

  • Stay connected with your team — iron sharpens iron.

  • Set goals, crush them, and move to the next level.

What It Takes
  • A winner’s mindset — you hate losing more than you love winning.

  • Confident, coachable, and relentless.

  • Self-disciplined with a drive to grow and dominate your craft.

  • Background in sports, leadership, or competition is a huge plus.

Requirements
  • Clean background check, valid driver’s license, and reliable transportation.

  • Active Health & Life License (or ready to get one — we’ll help and reimburse).

  • Bachelor’s degree or equivalent professional experience.

Compensation & Perks
  • Weekly draw + uncapped commissions — your effort writes your paycheck.

  • Monthly bonuses, quarterly stock shares, and long-term renewal income.

  • Paid incentive trips to top destinations — earn your spot and enjoy it.

  • Health, dental, and vision benefits after 60 days.

  • Promotions based solely on performance — no politics, just results.

  • A strong, winning culture built on accountability, growth, and excellence.

Join a team that competes to win.
Own your career. Build your legacy.

Vacancy posted 11 days ago
Similar jobs that could be interesting for youBased on the Direct Sales Representative in Winchester, KY vacancy
  •  ...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... 
    Suggested
    Weekly pay
    Work experience placement
    Work at office

    SUMMIT BUSINESS GROUP, LLC

    Winchester, KY
    4 days ago
  •  ...individual who is eager to enter the dynamic and competitive field of sales. This position is designed for those at an entry level, and...  ...opportunities. Position Overview: This is an outside direct sales position focused on your dedicated sales territory. We'll... 
    Suggested
    Weekly pay
    Work experience placement
    Local area

    Alleviation Enterprise LLC

    Winchester, KY
    11 days ago
  •  ...Job Description Job Description Join Our Team at True North Group! Position: Direct Sales Representative Number of Openings: 1 Territory Sales Position Available   About Us: At True North Group, we’re more than just an insurance agency – we’re dedicated to... 
    Suggested
    Weekly pay
    Work experience placement
    Local area
    Flexible hours

    True North Group LLC.

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

     ...Job Description Job Description Entry-Level Sales Representative   About Us At Cleft of the Rock , we believe in standing firm in...  ...support to both businesses and individual clients. You’ll work directly with business owners, decision-makers, and individuals to... 
    Suggested
    Full time
    For contractors
    Local area

    Cleft of the Rock, Inc.

    Winchester, KY
    11 days ago
  •  ...Entry Level Direct Sales Position 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... 
    Suggested
    Weekly pay

    SUMMIT BUSINESS GROUP, LLC

    Winchester, KY
    2 days ago
  • $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 work
    Work from home
    Flexible hours

    HMG Careers

    Winchester, KY
    1 day ago
  •  ...Job Description Job Description Our sales team is growing, and we are looking for a sharp and energetic new individual to grow with us! Ideally, we are looking for candidates with previous sales experience who have outgrown working in a call center or door-to-door... 
    Weekly pay
    Full time
    Work experience placement
    Work at office
    Local area

    Altitude Development Group

    Winchester, KY
    13 days ago
  • $75k - $95k

     ...Job Description Job Description B2B Sales Representative     About Us At Cleft of the Rock , we help businesses and individuals...  ...with your natural ability to connect with others. You'll work directly with business owners, managers, and decision-makers to provide... 
    Weekly pay
    Full time
    For contractors
    Monday to Friday
    Weekend work

    Cleft of the Rock, Inc.

    Winchester, KY
    20 days ago
  •  ...accountability, pride, and high standards.   What You’ll Do Train and mentor new agents, giving them the tools, confidence, and direction to succeed. Work alongside families, business owners and employees as you demonstrate and teach the value of supplemental... 
    Weekly pay

    Alpine Legacy Group

    Winchester, KY
    4 days ago
  •  ...is recognized and rewarded.   Position Overview: We hire for potential, not just experience. You don't need a background in sales—our training program covers licensing, product knowledge, and proven client acquisition strategies. What matters is your ability to... 
    For contractors
    Self employment

    Executive Financial Partners LLC

    Winchester, KY
    11 days ago
  •  ...challenges, and deliver measurable results. We're looking for a Lead Sales Representative who thrives in a fast-paced, results-driven environment,...  ...track record of success. You'll receive hands-on training, direct mentorship from top performers, and the tools to make a... 
    For contractors
    Self employment

    Executive Financial Partners LLC

    Winchester, KY
    18 days ago
  •  ...Job Description Job Description Position: - Sales Representative and Field Trainer About Us: We are looking for current or former...  ...the field" mentality. Your hard work and dedication will be directly reflected in your paycheck, making every sale feel like a win... 
    Weekly pay
    Work experience placement
    Work at office

    Summit Business Group

    Winchester, KY
    a month ago
  • $75k

     ...your chance to earn like a highly educated professional—our proven products and systems are your roadmap to becoming a top earner in sales. If you’re prepared to unlock your full potential, let us show you how to build a lucrative and rewarding future. Why Join... 
    Flexible hours
    Night shift

    Platinum Supplemental Insurance

    Winchester, KY
    1 day ago
  • $400 per month

     ...providing amazing customer experiences while delivering on all sales goals! Wireless Retail with 5G will be one of the most...  ...and grow your income! Responsibilities As a Retail Sales Representative, you are the face of our company and the most important position... 
    Hourly pay
    Weekend work
    Day shift
    Afternoon shift

    Connectivity Source I T-Mobile Authorized Retailer at Big Sp...

    Winchester, KY
    8 days ago
  •  ...Loan Sales Specialist At OneMain, Loan Sales Specialists empower customers by listening to their needs and providing access to friendly...  ...in a competitive atmosphere where hard work and dedication directly influence success. This role provides rewarding professional... 
    Local area
    Monday to Friday

    OneMain Holdings

    Winchester, KY
    4 days ago
  •  ...Job Description Job Description We’re growing our sales team and looking for a driven, energetic individual to join us and take their career to the next level! While prior experience in sales or leadership is a plus, it's not required—we're seeking the best fit for... 
    Weekly pay
    Work experience placement
    Local area

    Alleviation Enterprise LLC

    Winchester, KY
    11 days ago
  •  ...lifetime? Join our team today to help our customers celebrate life and express love! Your role at Kay Jewelers: As a part of our Sales Team you are responsible for providing a superior experience to our valued customers. In addition, you will: Engage customers in... 
    Base plus commission
    Full time
    Part time
    Seasonal work
    Immediate start
    Flexible hours
    Night shift
    Weekend work

    Kay Jewelers

    Winchester, KY
    4 days ago
  •  ...Lifeline Field Sales Representative Summary: Join our team as a Lifeline Field Sales Representative in Oklahoma, California, Kansas, or Kentucky. In this vital role, you will qualify and enroll customers in the Lifeline Program, making a significant impact in your... 
    Work at office

    Galaxy Distribution LLC

    North Middletown, KY
    5 days ago

Do you want to receive more vacancies?

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