Outside Sales Representative and Trainer

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

Benefits offered by this job

Training & mentorship

Draw pay + commissions

Incentive programs

Growth opportunities

Supportive team

Job summary

Cleft of the Rock is seeking an Outside Sales Representative & Trainer to connect with local business owners, present insurance solutions, and train junior team members. This in-person, B2B and individual sales role offers comprehensive training, draw pay with commissions and bonuses, and a mission-driven team focused on service and impact.

The position emphasizes relationship-building, mentoring, and regular client follow-ups to ensure satisfaction and long-term support, with licensing

Qualifications

• 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.

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.

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:

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