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

Senior Sales Representative

Alpine Legacy Group

Job Description

Job Description

At Alpine Legacy Group, we don’t wait for success to show up—we build it with our own two hands. This is a place for those who believe in hard work, personal responsibility, and the kind of grit that built this country from the ground up. Experience is appreciated, but it’s not what defines you here. What matters most is your character—your resilience, your drive, and your ability to lift others higher. We proudly serve families and small to medium sized businesses through supplemental health insurance, protecting what matters most. Now, we’re looking for strong leaders ready to step forward and train the next generation.

We’re growing quickly and searching for trainers who want more than a position—they want purpose. This role is for someone who thrives on developing people, sharpening skill sets, and helping others rise to their full potential. Your advancement isn’t tied to tenure; it’s tied to the results you create and the leaders you build. You’ll have the autonomy to guide, mentor, and influence the future of our team, backed by proven systems and a culture grounded in 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 health insurance.


  • Lead by example—mastering proven systems so you can teach them with clarity and conviction.


  • Set bold goals for yourself and your team, push for excellence, and help drive strong performance across the board.


What You Need to Bring

  • A strong work ethic and a genuine desire to lead from the front.


  • Confident communication and the ability to guide others with patience and purpose.


  • A coachable spirit—you live the same teachability you expect from your team.


  • Prior experience is appreciated, but not required—our training will prepare you to lead effectively.

What You’ll Earn
  • Weekly pay + uncapped commissions tied to production and team development.


  • Performance bonuses, vested renewals, and share-based incentives.


  • Company-paid incentive trips that reward top-tier leadership and effort.


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


  • A clear path to advanced leadership roles for trainers who consistently develop high-performing teams.


Why Alpine Legacy Group

We are a team built on grit, heart, and the belief that every person—no matter where they start—can build a life they’re proud of. We train hard, hold each other accountable, and celebrate our wins like a family. Many of our top leaders began with little more than ambition and drive. They rose because they were willing to work, willing to learn, and willing to lead.

If you’re ready to lead from the front and help develop the next generation of leaders, this is your moment to build a career and a legacy that stands out.

 

Vacancy posted 22 days ago
Similar jobs that could be interesting for youBased on the Senior Sales Representative in Winchester, KY vacancy
  • $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... 
    Suggested
    Remote work
    Work from home
    Flexible hours

    HMG Careers

    Winchester, KY
    1 day ago
  • $70k - $130k

     ...Tax Senior A reputable public accounting firm in the area is looking to add a Tax Senior to their team. This stable and growing firm offers clients valuable knowledge and expertise in tax. Due to the recent growth of the firm, there is an opportunity for a Tax Senior... 
    Senior
    Local area

    gpac

    Winchester, KY
    1 day ago
  • Comfort Systems USA is looking for a Project Manager to lead complex electrical construction projects. This role involves overseeing all phases from preconstruction to closeout, while ensuring financial performance and client satisfaction. The ideal candidate will have ...
    Senior

    Comfort Systems USA

    Winchester, KY
    4 days ago
  • A leading electrical contracting company is seeking a Foreman Electrician to oversee and mentor a crew of Helpers, Apprentices, and Journeyman electricians. The Foreman will lead by example, ensuring high-quality work while managing material lists and production schedules...
    Senior
    Weekend work

    Comfort Systems USA

    Winchester, KY
    3 days ago
  • $91k - $110k

     ...assistance available, no visa sponsorship Industry: Environmental Services Compensation : $91,000-$110,000 Overview We are seeking a Senior Cost Accountant responsible for standard costing, budgeting, and cost variance analysis. This role offers opportunities for growth... 
    Senior
    Work at office
    Visa sponsorship
    Relocation package

    Nelson Recruiting Agency

    Winchester, KY
    4 days ago
  •  ...has been committed to helping our valued clients and supporting our team's personal and professional development. As we expand our sales team into new local markets, we're looking for individuals who value taking control of their income, maintaining a healthy work/life... 
    Weekly pay
    Work experience placement
    Local area

    Alleviation Enterprise LLC

    Winchester, KY
    4 days ago
  • $76k - $109k

    Join to apply for the Senior Financial Analyst role at Danimer Scientific Location: Lexington, KY Salary: $76,000.00 - $109,000.00 Posted: 1 month ago Job Summary We are seeking a Senior Financial Analyst, FP&A to drive financial planning and analysis in a manufacturing... 
    Senior
    Full time

    Danimer Scientific

    Winchester, KY
    4 days ago
  • $136k - $210k

     ...airport. Position Summary We have an opportunity for a Senior Counsel to join our team. In this role, you will handle a variety...  ...or hiring process. Notice to Agency and Search Firm Representatives: Catalent Pharma Solutions (Catalent) is not accepting unsolicited... 
    Senior
    Contract work
    Work at office
    Local area

    Catalent Inc

    Winchester, KY
    1 day ago
  • Senior Manager, Production About SiteCatalent’s Winchester, KY site is the company’s flagship U.S. manufacturing location for large...  ...or hiring process.Notice to Agency and Search Firm Representatives: Catalent Pharma Solutions (Catalent) is not accepting unsolicited... 
    Senior
    Full time
    Work at office
    Local area
    Monday to Friday
    Shift work

    Catalent

    Winchester, KY
    2 days ago
  • Cardinal Hill Rehabilitation Hospital, part of Encompass Health, seeks a Senior Case Manager to coordinate complex patient care across our inpatient rehabilitation continuum. In this role, you’ll lead discharge planning, manage caseloads, conduct psychosocial assessments... 
    Senior

    Cardinal Hill Rehabilitation Hospital

    North Middletown, KY
    11 days 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
    9 hours ago
  •  ...Sales Consultant The purpose of the Sales Consultant is to play a pivotal role in assisting customers with their agricultural and household needs. With a store knowledge of farm equipment, power equipment, tools, and home essentials, you will provide exceptional customer... 

    Rural King

    Winchester, KY
    3 days ago
  • Select how often (in days) to receive an alert: Consumer Lending Sales Specialist - Full Time Address :3 North Bloomfield Rd.,Winchester,Kentucky,United States -40391 Bi-Lingual Spanish is a plus!! Since 1997, Advance America has helped millions of hardworking people... 
    Full time
    Bank staff
    Work at office

    Advance America, Cash Advance Centers, Inc.

    Winchester, KY
    23 hours ago
  •  ...integrity, deliver results, and stand by the people and communities we represent. We believe in discipline, hard work, and doing what matters...  ...and gain real-world experience that sets you apart. Sales experience is not required—what matters most is your ambition,... 
    For contractors
    Self employment

    Executive Financial Partners LLC

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

     ...Job Description Job Description B2B Sales Representative About Us At Cleft of the Rock , we help businesses and individuals secure supplemental insurance solutions that protect what matters most. Our team values achievement, relationships, and making a... 
    Weekly pay
    Full time
    For contractors
    Weekend work

    Cleft of the Rock, Inc.

    Winchester, KY
    23 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
    7 days ago
  •  ...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... 
    Weekly pay
    Local area
    Flexible hours

    True North Group LLC.

    Winchester, KY
    6 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 service, compassion, and integrity. Our mission is to help businesses and individuals protect what matters most — their people... 
    Full time
    For contractors
    Local area

    Cleft of the Rock, Inc.

    Winchester, KY
    17 days 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 |T-Mobile Authorized Retailer

    Winchester, KY
    16 days ago
  •  ...Job Description Job Description Company: Summit Business Group Position: Direct Sales Representative Number Of Openings: 1 Territory Sales About Us: Summit Business Group is a rapidly growing insurance agency committed to providing outstanding... 
    Weekly pay
    Work experience placement
    Work at office

    Summit Business Group

    Winchester, KY
    18 days ago
  •  ...takes pride in their work, loves helping others, and thrives in a positive, goal-driven environment. Position Overview As a new Sales Professional with Alpine Legacy Group, you’ll begin with our comprehensive training program — a blend of online learning, field mentorship... 
    Work experience placement
    Start working today
    Local area
    Flexible hours

    Alpine Legacy Group

    Winchester, KY
    21 days ago
  • 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...
    Weekly pay
    Local area

    Alpine Legacy Group

    Winchester, KY
    7 days 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
    12 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... 
    Weekly pay
    Work experience placement
    Local area
    Flexible hours

    True North Group LLC.

    Winchester, KY
    10 days ago
  •  ...surrounding states. We are seeking an experienced Commercial Construction Estimator to join our growing preconstruction team. Now Hiring: Senior Commercial Construction Estimator | Winchester, KY!!! Ready to turn plans into successful projects before construction even... 
    Senior
    For subcontractor
    Immediate start

    Codell Construction Company

    Winchester, KY
    18 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
    4 days 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... 
    Weekly pay

    Summit Business Group

    Winchester, KY
    10 days ago

Do you want to receive more vacancies?

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