B2B Sales Representative

Cleft of the Rock, Inc.; Winchester (KY); On-site; USD 75,000 - 95,000; Full time

Benefits offered by this job

Training & mentorship

Draw pay + commissions

Bonuses

Stock options

Trips

Advancement opportunities

Supportive team

Job summary

Cleft of the Rock is hiring a B2B Sales Representative in Kentucky. You will connect with business owners and decision-makers, presenting insurance solutions to fit needs and drive results.

You will build a personal book of business, earn draw pay, commissions, and bonuses, and work in a role that rewards achievement, impact, and collaboration within a supportive team.

Qualifications

• Licensed in Health & Life or willing to obtain (reimbursement provided).

Responsibilities

• Develop strong relationships with businesses and their employees in your territory
• Deliver compelling presentations to business leaders and employee groups
• Build and grow your own book of business with measurable results
• Follow up on leads, schedule appointments, and provide exceptional client support
• Collaborate with your manager to set ambitious sales targets and exceed them

Skills

Relationship building

Sales presentations

Negotiation

Business development

Job description

B2B Sales Representative

About Us

At Cleft of the Rock, we help businesses and individuals secure supplemental insurance solutions that protect what matters most. Our team values achievement, relationships, and making a tangible impact. We provide an environment where ambitious, driven professionals can thrive while helping others succeed.

Your Role

As a B2B Sales Representative, you will combine your ambition with your natural ability to connect with others. You'll work directly with business owners, managers, and decision-makers to provide insurance solutions that meet their needs and deliver results. Success in this role comes from building trust, guiding clients, and achieving measurable outcomes.

Key Responsibilities:

• Develop strong relationships with businesses and their employees in your territory
• Deliver compelling presentations to business leaders and employee groups
• Build and grow your own book of business with measurable results
• Follow up on leads, schedule appointments, and provide exceptional client support
• Collaborate with your manager to set ambitious sales targets and exceed them

What We Offer

• Comprehensive training and mentorship to accelerate your success
• Weekly draw pay, plus commissions and bonuses with high earning potential
• Performance-based incentives including cash rewards, stock options, and trips
• Advancement opportunities based on achievement and impact
• A supportive team environment that values collaboration and results

Who You Are

• Ambitious, goal-oriented, and driven to achieve measurable results
• Skilled at building relationships and guiding others toward solutions
• Confident presenting to business leaders and groups of employees
• Empathetic and service-minded, balancing achievement with helping others
• Licensed in Health & Life or willing to obtain a license (reimbursement provided)

Company: Cleft of the Rock

Employment Type: Full-Time | Independent Contractor
Compensation: $75,000 - $95,000 per year with draw pay, commissions, and bonuses
Schedule: Monday–Friday, weekends as needed
Location: In-person, business-to-business sales

Join Us

This is a career for someone who wants to make an impact, achieve success, and help others. Cleft of the Rock offers a supportive environment with clear pathways for growth and recognition.

Learn more: www.thecleftoftherock.com