Outside Sales Representative

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.

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