Outside Sales Representative

About Us

At Cleft of the Rock
, we help businesses and individuals protect what matters most. Our team is built on trust, empathy, and genuine care
. We don't just sell insurance, we provide solutions that make a difference.

We are looking for an Outside Sales Representative who enjoys connecting with people and building long-term relationships. You will visit businesses, meet decision-makers, and guide clients through supplemental insurance options that meet their needs. Your success comes from helping others feel secure and confident in their choices.

• Meet face-to-face with business owners, managers, and employees in your territory
• Lead presentations to small groups and larger teams (1–100+ employees)
• Build and maintain your own book of business
• Follow up on leads, schedule appointments, and support clients throughout the process
• Work closely with your manager to set goals and track progress

• Hands-on training and ongoing mentorship
• Weekly draw pay plus commissions and performance bonuses
• Incentive trips, cash rewards, and stock opportunities
• Flexible schedule as your client base grows
• A collaborative and caring team environment where service comes first

• Passionate about helping others and building meaningful relationships
• Self-motivated, independent, and resilient
• Professional, approachable, and confident presenting to groups
• Licensed in Health & Life or willing to obtain a license with reimbursement provided

Company:
Cleft of the Rock
Compensation: $75,000 - $95,000 per year with draw pay, commissions, and bonuses

Schedule:

Monday–Friday, weekends as needed

Location:

Remote/Hybrid In-person, business-to-business sales

This is more than a sales role. It is an opportunity to impact lives, grow your career, and earn great income while working with a supportive team.
Cleft of the Rock is the right place for someone ready to meet new people, make a difference, and succeed in a meaningful career.

Learn more: