Outside Sales Representative and Trainer

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

Benefits offered by this job

Training program

Draw pay

Bonuses

Travel opportunities

Leadership development

Job summary

Cleft of the Rock, Inc. is seeking an Outside Sales Representative & Trainer to connect with local business owners and individuals, presenting supplemental insurance solutions while mentoring teammates. This role combines field sales with hands-on training to grow the team and drive customer success.

You will cultivate relationships, deliver engaging presentations, and provide ongoing support to clients while advancing professional skills and leadership abilities within a mission-driven company.

Qualifications

• Licensed in Health & Life or willing to obtain a license (licensing assistance and reimbursement provided).
• Strong focus on compassionate service and building trust with clients.

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

Customer service

Mentoring

Communication

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