Outside Sales Representative and Trainer
Posted 2026-05-06Outside 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.