B2B Sales Representative Entry Level

Cleft of the Rock, Inc.; Glasgow (KY); On-site; USD 65,000 - 85,000; Full time

Benefits offered by this job

Comprehensive training

Licensing assistance

Reimbursement

Unlimited earning potential

Job summary

Cleft of the Rock, Inc. is hiring an entry-level B2B Sales Representative to work with business owners and decision-makers, guiding them toward supplemental insurance solutions.

You will educate, consult, and support clients through the sales process, ensuring they feel confident and cared for in every interaction. We offer comprehensive training, licensing assistance, and reimbursement, with an uncapped commission structure.

Qualifications

• Empathetic and service-minded with a genuine desire to help businesses and teams.
• Strong communication skills and the ability to educate and consult clients.
• Ambitious, goal-oriented, and capable of building long-term relationships.

Responsibilities

• Build strong relationships with businesses in your territory.
• Conduct needs-based consultations to identify supplemental insurance options.
• Present and enroll clients in programs protecting their teams.
• Follow up to ensure ongoing satisfaction and lasting relationships.
• Participate in training and mentorship to grow skills and impact.

Skills

Empathy

Service-minded

Communication

Relationship-building

Driven

Job description

B2B Sales Representative - Entry Level

About Us

At Cleft of the Rock, we believe business is about people first. Our mission is to help businesses and their teams secure supplemental insurance solutions that protect what matters most. We focus on understanding needs, providing compassionate guidance, and ensuring clients feel supported and valued.

We are a team that thrives on service, empathy, and building meaningful relationships. If helping others and making a tangible difference motivates you, this is the place to grow both personally and professionally.

Your Role

As a B2B Sales Representative, you'll leverage your natural empathy and relationship-building skills to guide business owners and decision-makers toward solutions that genuinely help their employees. You'll educate, consult, and support clients throughout the sales process, ensuring they feel confident and cared for.

What You'll Do:

• Build strong, trusting relationships with businesses in your territory.
• Conduct needs-based consultations to identify the best supplemental insurance options.
• Present and enroll clients in programs that protect their teams.
• Follow up to ensure ongoing satisfaction and long-term relationships.
• Participate in training and mentorship to continue growing your skills and impact.

What We Offer:

• Comprehensive training and hands-on mentorship.
• Licensing assistance and reimbursement to help you get started.
• A team culture focused on empathy, service, and collaboration.
• Unlimited earning potential with commission-based pay (average $65,000–$85,000 annually for entry-level agents).
• Optional base draw during your first 6 weeks to support your transition.

Who You Are:

• You are empathetic, service-minded, and thrive when helping others.
• You are driven, ambitious, and want to grow both personally and professionally.
• You communicate with warmth, professionalism, and authenticity.
• You enjoy building strong relationships and being a trusted advisor.
• You are motivated by making a positive impact while achieving your own goals.

Company:Cleft on the Rock
Employment Type: Full-Time | Independent Contractor
Industry: Supplemental Insurance | Business-to-Business Sales
Compensation: Commission-Based (Average $65,000–$85,000 per year) — Optional base draw for your first few weeks to help get you started
Location: Local Territory (In-person)

Join Us

If you're ready to use your talents for empathy, service, and connection to make a real impact in the lives of businesses and their teams, Cleft of the Rock is the right place for you.

Learn more at:

www.thecleftoftherock.com