Outside Sales Representative and Trainer

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

Outside Sales Representative & Trainer

About Us

At Cleft of the Rock, we believe in serving people first. We help businesses and individuals protect what matters most through supplemental insurance solutions - but our real mission is to care for others and provide peace of mind. Our culture is built on compassion, connection, and purpose.

Your Role

As an Outside Sales Representative & Trainer, you'll do more than sell - you'll serve. You'll connect with local business owners, listen to their needs, and help them find insurance solutions that make a real difference. Along the way, you'll also train and mentor others, using your natural warmth and people skills to help your team grow and succeed.

Key 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

What We Offer

• Comprehensive training and mentorship to help you thrive
• Weekly draw pay plus commissions and bonuses
• Incentive programs including cash rewards, recognition, and travel opportunities
• Opportunities for professional growth and leadership development
• A supportive, mission-driven team environment centered on people and purpose

Who You Are

• Compassionate, service-minded, and genuinely care about helping others
• Skilled at building trust and creating lasting relationships
• Encouraging and supportive - a natural mentor and team player
• Positive, motivated, and driven by making a meaningful impact
• Licensed in Health & Life or willing to obtain a license (licensing assistance and reimbursement provided)

Company: Cleft of the Rock
Compensation: $85,000 - $105,000 per year with draw pay, commissions, and bonuses
Schedule: Monday-Friday, weekends as needed
Location: In-person, business-to-business and individual sales

Join Us

If you're looking for a career where you can build relationships, serve others, and make a lasting impact, Cleft of the Rock offers the environment, training, and purpose to help you succeed as an Outside Sales Representative & Trainer.

Learn more: www.thecleftoftherock.com