Outside Sales Representative

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

Benefits offered by this job

Training & mentorship

Draw pay + commissions

Incentive trips

Flexible schedule

Collaborative environment

Job summary

Cleft of the Rock is seeking an Outside Sales Representative to visit businesses, meet decision-makers, and guide clients through supplemental health and life insurance options. You will build a personal book of business and drive solutions in a remote/hybrid territory.

The role emphasizes relationship-building, self-motivation, and clear presentations to groups. You’ll receive training, draw pay plus commissions, and potential bonuses as you grow your client base in a supportive team.

Qualifications

• Must be licensed in Health & Life or willing to obtain license with reimbursement provided.
• Excellent interpersonal and relationship-building abilities.
• Comfort presenting to groups and meeting with decision-makers.
• Willingness to work remote/hybrid and travel in territory.

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

Relationships

Presentation

Self-motivation

People skills

Education

Health & Life license or willingness 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 with draw 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