Sales Representative and Trainer

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

Benefits offered by this job

Comprehensive training and mentorship

Weekly draw pay plus commissions and}

Bonuses and incentives

Professional development and careerAdv

Job summary

Cleft of the Rock is seeking a Sales Representative & Trainer to combine hands-on insurance sales with coaching to help the team grow. You will engage business owners, managers, and employees with compelling presentations, build a robust client book, and mentor new teammates for skill development.

The role emphasizes patient, service-oriented sales with a focus on positive client experiences, backed by comprehensive training and growth opportunities in a collaborative culture.

Qualifications

• 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).

Responsibilities

• Present insurance solutions to business owners, managers and employees.
• 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 experience

Public speaking

Coaching

Relationship building

Education

Health & Life license (or ability 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:Cleft of the Rock
Compensation:$85,000 - $105,000 per year withdraw 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.