Outside Sales Representative and Trainer

Job Description

Job Description

Outside Sales Representative & Trainer Mission First. Standards Matter. Leadership Earned.

Divinity Group provides supplemental insurance solutions that help businesses protect their people. We are seeking a Sales Representative & Trainer who operates with discipline, takes ownership of outcomes, and leads by example. This role is built for individuals who excel in structured environments, follow proven systems, and execute consistently in the field.

Success in this position is driven by preparation, accountability, and commitment to the team's mission.

About the Role

This is a field-based, business-to-business sales position working directly with decision-makers. You will be responsible for personal production while developing others through hands-on coaching and leadership. The role balances autonomy in the field with clear expectations, performance metrics, and support from leadership.

Role Overview

• Role Type: Full-Time Independent Contractor

• Work Location: Remote, with B2B field operations in your local community

• Schedule: MondayFriday, with occasional weekends as needed

• Compensation: $75,000$95,000 annually (base draw, commissions, bonuses)

Key Responsibilities

Sales & Execution

• Conduct face-to-face B2B sales with professionalism and precision

• Execute a structured sales process and meet defined performance standards

• Build trust with business owners through integrity and consistency

• Maintain accurate reporting and performance tracking

Training & Leadership

• Train and develop new representatives through field-based coaching

• Set the standard for preparation, conduct, and work ethic

• Provide clear direction, feedback, and accountability

• Support team readiness and continuous improvement

Qualifications

• 35 years of experience in structured, high-accountability environments

• Proven success in B2B sales; leadership or training experience preferred

• Strong communication skills and situational awareness

• Coachable, dependable, and mentally tough

• Comfortable operating independently while following established systems

• Ability to perform in fast-paced, goal-driven conditions

Discipline, adaptability, and execution are critical for success in this role.

Why Divinity Group

• Performance-based compensation with uncapped earning potential

• Clear advancement path into leadership and training roles

• Licensing assistance and reimbursement

• Ongoing professional development and mentorship

• Team culture built on standards, trust, and accountability

• Purpose-driven work that makes a real impact for businesses and employees

About Divinity Group

Divinity Group develops professionals who lead with integrity, execute with discipline, and serve with purpose. We emphasize structure, accountability, and growth to create long-term opportunities for high performers.

Learn more at