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Cleft of the Rock, Inc. is seeking an Outside Sales Representative to connect with business owners and decision-makers, guiding clients through supplemental health and life insurance options.
You will build your own book of business, lead presentations for groups, follow up on leads, and work with your manager to set goals. The role offers hands-on training, draw pay, commissions, bonuses, and a flexible schedule in a remote/hybrid B2B setting.
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 withdraw 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: www.thecleftoftherock.com