B2B Outside Sales Pro — Insurance Solutions

Cleft of the Rock, Inc.; Cape Girardeau (MO); Hybrid; USD 75,000 - 95,000; Full time

Benefits offered by this job

Hands-on training

Draw pay + commissions

Incentive trips & stock opportunities

Flexible schedule

Collaborative team

Job summary

Cleft of the Rock, Inc. is seeking an Outside Sales Representative to visit businesses, meet decision-makers, and guide clients through supplemental insurance options. You will build a personal book of business and grow your territory through relationship selling.

You’ll receive hands‑on training, weekly draw pay with commissions and bonuses, and a supportive team culture. This role offers a remote/hybrid setup and licensure reimbursement in Health & Life where needed.

Qualifications

• Face-to-face sales to business owners, managers and employees.
• Proven ability to build lasting client relationships and meet sales targets.
• Comfort presenting to groups and leading discussions.

Responsibilities

• 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

Skills

Relationship building

Self-motivated

Public speaking

Presentation skills

Education

License in Health & Life or willingness to obtain

Job description

Cleft of the Rock, Inc. is seeking an Outside Sales Representative to visit businesses, meet decision-makers, and guide clients through supplemental insurance options. You will build a personal book of business and grow your territory through relationship selling.

You’ll receive hands‑on training, weekly draw pay with commissions and bonuses, and a supportive team culture. This role offers a remote/hybrid setup and licensure reimbursement in Health & Life where needed.