Outside Sales Representative

Cleft of the Rock•Paducah, KY
•Hybrid

About The Position

Cleft of the Rock is seeking an Outside Sales Representative to build relationships with businesses and individuals and help clients select supplemental insurance options. The role involves visiting businesses, meeting decision-makers, presenting insurance options, and supporting clients throughout the sales process. The position is described as remote/hybrid with in-person business-to-business sales. The schedule is Monday–Friday, with weekends as needed. Compensation is $75,000–$95,000 per year, including draw pay, commissions, and bonuses.

Requirements

  • Be passionate about helping others and building meaningful relationships.
  • Be self-motivated, independent, and resilient.
  • Be professional, approachable, and confident presenting to groups.
  • Hold a Health & Life license or be willing to obtain one; reimbursement is provided.

Responsibilities

  • Meet face-to-face with business owners, managers, and employees in an assigned territory.
  • Lead presentations for small groups and larger teams of 1–100+ employees.
  • Build and maintain a book of business.
  • Follow up on leads, schedule appointments, and support clients throughout the process.
  • Work with a manager to set goals and track progress.

Benefits

  • Hands-on training and ongoing mentorship.
  • Weekly draw pay, commissions, and performance bonuses.
  • Incentive trips, cash rewards, and stock opportunities.
  • Flexible schedule as the client base grows.
  • Collaborative and supportive team environment.
  • License reimbursement.
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