B2B Sales Representative Entry Level

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

Benefits offered by this job

Comprehensive training

Licensing assistance

Reimbursement

Unlimited earning potential

Base draw during first 6 weeks

Job summary

Cleft of the Rock, Inc. in Kentucky is seeking an entry-level B2B Sales Representative to build relationships with local businesses and guide decision-makers toward supplemental insurance solutions for their teams.

You will learn consultative sales, participate in training, and earn commissions with a base draw during the first weeks, targeting personal growth and meaningful client impact in a collaborative, service-driven environment.

Qualifications

• Empathy-driven service mindset.
• Ability to build rapport with business owners.

Responsibilities

• Build strong, trusting relationships with local businesses.
• Conduct needs-based consultations to identify optimal insurance options.
• Present and enroll clients in programs protecting their teams.
• Follow up to ensure ongoing satisfaction and long-term relationships.
• Participate in training and mentorship to grow skills and impact.

Skills

Empathy

Relationship-building

Communication

Consultative selling

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