B2B Outside Sales Pro - Insurance Solutions (Remote)

Cleft of the Rock, Inc.; Olive Branch (MS); Hybrid; USD 75,000 - 95,000; Full time

Benefits offered by this job

Training & mentorship

Draw pay + commissions

Incentive trips

Stock options

Flexible schedule

Job summary

Cleft of the Rock is seeking an Outside Sales Representative to visit businesses, meet decision-makers, and guide clients through supplemental insurance options that fit their needs.

You will build a personal book of business, follow up on leads, and present to groups while collaborating with your manager to set goals and achieve targets. This role offers draw pay, commissions, bonuses, and a flexible schedule.

Qualifications

• License in Health & Life or willingness to obtain (reimbursement provided).
• Experience in face‑to‑face sales and B2B environments.
• Strong communication and presentation skills.

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

Public speaking

Self-motivation

License in Health & Life

Education

Health & Life License

Job description

Cleft of the Rock is seeking an Outside Sales Representative to visit businesses, meet decision-makers, and guide clients through supplemental insurance options that fit their needs.

You will build a personal book of business, follow up on leads, and present to groups while collaborating with your manager to set goals and achieve targets. This role offers draw pay, commissions, bonuses, and a flexible schedule.