Outside Sales Representative

Cleft of the Rock, Inc.; Shepherdsville (KY); Hybrid; USD 75,000 - 95,000; Full time

Benefits offered by this job

Hands-on training and ongoingMentor-?

Weekly draw pay plus commissions and Q

Incentive trips, cash rewards, and,]

Flexible schedule as your client base

Collaborative team environment

Job summary

Cleft of the Rock, Inc. is seeking an Outside Sales Representative to visit businesses, meet decision-makers, and guide clients through supplemental insurance options that meet their needs.

You will build lasting relationships and help clients feel secure in their choices. You will meet with business owners and employees in your territory, lead presentations for groups, and manage your own book of business while collaborating with your manager to set and monitor goals.

Qualifications

• Passionate about helping others and building meaningful relationships.
• Self-motivated, independent, and resilient.
• Professional, approachable, and confident presenting to groups.
• Licensed in Health & Life or willing to obtain a license with reimbursement provided.

Responsibilities

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

Skills

People skills

Relationship building

Professional presentation

Education

Health & Life insurance license (or willing to obtain)

Job description

Outside Sales Representative

About Us

At Cleft of the Rock, we help businesses and individuals protect what matters most. Our team is built on trust, empathy, and genuine care. We don't just sell insurance, we provide solutions that make a difference.

The Role

We are looking for an Outside Sales Representative who enjoys connecting with people and building long-term relationships. You will visit businesses, meet decision-makers, and guide clients through supplemental insurance options that meet their needs. Your success comes from helping others feel secure and confident in their choices.

What You Will Do:

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

What We Offer

• Hands-on training and ongoing mentorship
• Weekly draw pay plus commissions and performance bonuses
• Incentive trips, cash rewards, and stock opportunities
• Flexible schedule as your client base grows
• A collaborative and caring team environment where service comes first

Who You Are

• Passionate about helping others and building meaningful relationships
• Self-motivated, independent, and resilient
• Professional, approachable, and confident presenting to groups
• Licensed in Health & Life or willing to obtain a license with reimbursement provided

Company:Cleft of the Rock
Compensation:$75,000 - $95,000 per year withdraw pay, commissions, and bonuses
Schedule:Monday–Friday, weekends as needed
Location:Remote/Hybrid In-person, business-to-business sales

Why Join Us

This is more than a sales role. It is an opportunity to impact lives, grow your career, and earn great income while working with a supportive team. Cleft of the Rock is the right place for someone ready to meet new people, make a difference, and succeed in a meaningful career.

Learn more: www.thecleftoftherock.com