Outside Sales Representative at Cleft of the Rock in Ashland, KY

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. The Role 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. What You Will Do: 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 What We Offer 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 Who You Are 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 Why Join Us 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