Outside Sales Representative — Supplemental Insurance

Job overview

The Outside Sales Representative role is described as remote/hybrid with in-person business-to-business sales in Shelbyville, KY. Compensation is $75,000–$95,000 per year, with draw pay, commissions, and bonuses. Cleft of the Rock helps businesses and individuals protect what matters through insurance solutions. The representative meets business decision-makers and employees, presents supplemental insurance options, and builds a book of business through follow-up and client support. The role helps clients understand coverage choices and supports the company’s relationship-based sales work.

What you'll do

• Meet face-to-face with business owners, managers, and employees in the assigned territory
• lead presentations for small and large groups
• build and maintain a book of business
• follow up on leads and schedule appointments
• support clients through the sales process
• work with a manager to set goals and track progress.

What we're looking for

Skills & competencies

outside sales representative

supplemental insurance

shelbyville ky

cleft of the rock

full-time

remote/hybrid

business-to-business sales

client relationships

group presentations

health and life license

$75k–$95k per year

commissions and bonuses

Work arrangement

• Weekend coverage required

Benefits & perks

• Weekly draw pay, commissions, and performance bonuses
• incentive trips, cash rewards, and stock opportunities
• hands-on training and ongoing mentorship
• flexible schedule as the client base grows.

Why this role

Offers hands-on training and ongoing mentorship, weekly draw pay plus commissions and performance bonuses, incentive trips, cash rewards, stock opportunities, and a flexible schedule as the client base grows. Applicants must hold a Health and Life license or be willing to obtain one, with reimbursement provided.

About the employer

Cleft of the Rock, Inc. is hiring for this role. Industry: Insurance Agencies and Brokerages. Sector: 52.