Sales Representative and Trainer

Cleft of the Rock, Inc.; Jonesborough (TN); Hybrid; USD 85,000 - 105,000; Full time

Benefits offered by this job

Comprehensive training

Draw pay + commissions + bonuses

Stock options and recognition programs

Professional development opportunities

Collaborative culture

Job summary

Cleft of the Rock, Inc. is seeking a Sales Representative & Trainer to blend hands-on insurance sales with coaching for teammates. The role emphasizes patient guidance, client care, and measurable outcomes in a collaborative environment.

The position offers comprehensive training, draw pay with commissions and bonuses, and opportunities for development. Location is remote/hybrid with B2B and individual sales focus.

Qualifications

• Calm, supportive and patient with a natural ability to guide and help others.
• Service-oriented and motivated by making a positive impact.
• Reliable and collaborative, focused on steady progress.
• Licensed in Health & Life or willing to obtain a license (reimbursement provided).

Responsibilities

• Meet with business owners, managers, and employees to present insurance solutions.
• Conduct individual and group presentations (small meetings or teams of 50+ employees).
• Build and maintain a book of business.
• Guide and support new team members, helping them develop their skills.
• Follow up on leads, schedule appointments, and maintain strong client relationships.
• Work with management to set achievable goals and support team success.

Skills

Sales skills

Coaching

Customer service

Communication

Reliability

Education

Health & Life license (or willingness to obtain)

Job description

Sales Representative & Trainer

About Us

At Cleft of the Rock, we provide supplemental insurance solutions that help businesses and individuals feel confident and secure. Our team values steadiness, collaboration, and care, fostering an environment where professionals who naturally support and guide others can thrive.

Your Role

As a Sales Representative & Trainer, you will help clients navigate insurance options while also mentoring and supporting your teammates. This role is ideal for someone who is patient, reliable, and focused on creating positive experiences for others. You'll combine hands‑on sales with coaching to help your team grow and succeed.

Key Responsibilities:

• Meet with business owners, managers, and employees to present insurance solutions
• Conduct individual and group presentations (small meetings or teams of 50+ employees)
• Build and maintain a book of business
• Guide and support new team members, helping them develop their skills
• Follow up on leads, schedule appointments, and maintain strong client relationships
• Work with management to set achievable goals and support team success

What We Offer

• Comprehensive training and mentorship to support your growth
• Weekly draw pay plus commissions and bonuses
• Incentives including cash rewards, stock options, and recognition programs
• Opportunities for professional development and advancement
• A collaborative, supportive culture where teamwork and client care come first

Who You Are

• Calm, supportive, and patient, with a natural ability to guide and help others
• Service-oriented and motivated by making a positive impact
• Reliable, collaborative, and focused on steady progress
• Licensed in Health & Life or willing to obtain a license (reimbursement provided)

Company:
Compensation:$85,000 - $105,000 per year with draw pay, commissions, and bonuses as an independent contractor
Schedule:Monday–Friday, weekends as needed
Location:Remote/Hybrid, business-to-business and individual sales

Join Us

This is a career where you can support clients, help your team grow, and make a meaningful impact every day. Cleft of the Rock provides the resources, culture, and support you need to succeed as a Sales Representative & Trainer.