Outside Sales Pro & Trainer — Mentorship & Growth

Cleft of the Rock, Inc.; Ashland (KY); On-site; USD 85,000 - 105,000; Full time

Benefits offered by this job

Comprehensive training and mentorship

Weekly draw pay plus commissions and a

Job summary

Cleft of the Rock in Ashland, KY is seeking an Outside Sales Representative & Trainer to connect with local business owners, present insurance solutions, and mentor teammates. This in-person, business-to-business role emphasizes relationship building and service.

You'll receive draw pay, commissions, and bonuses, with licensing assistance provided. Schedule is Monday–Friday, with weekends as needed, and there are opportunities for leadership development and growth.

Qualifications

• Compassionate, service-minded and care about helping others.
• Able to build trust and lasting relationships.
• Encouraging and supportive - a natural mentor and team player.
• Positive, motivated, and driven to make a meaningful impact.
• Licensed in Health & Life or willing to obtain a license; licensing assistance provided.

Responsibilities

• Build meaningful relationships with business owners, managers, and employees.
• Present supplemental insurance solutions that align with client needs.
• Conduct group presentations and one-on-one consultations.
• Train and support new team members, helping them build confidence and success.
• Follow up with clients regularly to ensure satisfaction and continued support.
• Work closely with your manager to set goals and grow your impact in the field.

Skills

Relationship building

Public speaking

Mentoring

Communication

Sales experience

Licensing

Job description

Cleft of the Rock in Ashland, KY is seeking an Outside Sales Representative & Trainer to connect with local business owners, present insurance solutions, and mentor teammates. This in-person, business-to-business role emphasizes relationship building and service.

You'll receive draw pay, commissions, and bonuses, with licensing assistance provided. Schedule is Monday–Friday, with weekends as needed, and there are opportunities for leadership development and growth.