Sales Rep & Trainer — Remote, Commissions & Bonuses

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

Benefits offered by this job

Comprehensive training & mentorship

Draw pay, commissions & bonuses

Professional development opportunities

Collaborative culture

Job summary

Cleft of the Rock, Inc. is seeking a Sales Representative & Trainer to blend client-facing sales with mentoring teammates. You’ll present insurance solutions to business owners and employees, conduct group and individual sessions, and help grow a robust book of business.

You’ll coach new teammates, stay patient and service-oriented, and work in a remote/hybrid environment with Monday–Friday scheduling and occasional weekend needs. Compensation includes draw, commissions, and bonuses.

Qualifications

• 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

Calm demeanor

Patient

Supportive

Collaborative

Education

Health & Life license

Job description

Cleft of the Rock, Inc. is seeking a Sales Representative & Trainer to blend client-facing sales with mentoring teammates. You’ll present insurance solutions to business owners and employees, conduct group and individual sessions, and help grow a robust book of business.

You’ll coach new teammates, stay patient and service-oriented, and work in a remote/hybrid environment with Monday–Friday scheduling and occasional weekend needs. Compensation includes draw, commissions, and bonuses.