Back to all jobs

Outside Sales Representative

Work from home Full-time role Hiring

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 Apply To This Job

More remote roles to explore

B2B Sales Representative Entry Level

Work from home Full-time role

B2B Sales Representative

Work from home Full-time role

Insurance Sales Representative

Work from home Full-time role

Senior Associate, Architect (Living)

Work from home Full-time role

Electrical BIM Specialist

Work from home Full-time role

Project Controls Schedule Lead

Work from home Full-time role

Staff Stormwater Transportation Engineer

Work from home Full-time role

Temporary Payroll Accountant

Work from home Full-time role

Temporary Payroll Accountant

Work from home Full-time role

Temporary Payroll Accountant

Work from home Full-time role

Tax Director - Remote - East Coast Based

Work from home Full-time role

People Services + Technology, Compensation Product Leader

Work from home Full-time role

Slovakian OPI/VRI Interpretation Vacancy

Work from home Full-time role

Looking for Online English Teacher (100% Remote) in Rochester, MN

Work from home Full-time role

Entry Level Data Entry Specialist – Remote Home-Based Position with arenaflex | Flexible Hours & Comprehensive Training Available

Work from home Full-time role

Join Today: [Entry level Remote jobs] Aetna Data Entry Remote

Work from home Full-time role

Experienced Customer Account Support Specialist for Dynamic Financial Services Team - 100% Remote Opportunity at blithequark

Work from home Full-time role

Experienced Early Childhood Education Professional - Early Learning Specialist for Infant and Toddler Development in Dunedin, FL

Work from home Full-time role

Experienced Remote Data Entry and Typing Associate for Dynamic Work-from-Home Opportunities with blithequark - No Prior Experience Necessary

Work from home Full-time role

New Notary Certification (Nationwide) - Become a Notary in New Jersey - Willingboro, New Jersey

Work from home Full-time role