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Outside Sales Representative and Trainer

Remote, USA Full-time Posted 2026-05-21

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
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