Outside Sales Representative and Trainer

Divinity Group • Oregon City, OR

2d • Remote

About The Position

Divinity Group is hiring an Outside Sales Representative and Trainer to sell supplemental insurance solutions to businesses and help develop other representatives. This field-based, business-to-business role involves working directly with decision-makers in the local community. The representative is responsible for personal sales production while providing hands-on coaching and leadership to others. The role combines field autonomy with defined expectations, performance metrics, and leadership support.

The position is remote, with B2B field operations in the local community. The schedule is Monday through Friday, with occasional weekends as needed. Compensation is listed as $75,000–$95,000 annually through a base draw, commissions, and bonuses. The role is described as full-time independent contractor work.

Divinity Group emphasizes structured execution, preparation, accountability, and consistent performance. The company describes its work as helping businesses protect their people and says it develops professionals who lead with integrity, execute with discipline, and serve with purpose.

Requirements

• 3–5 years of experience in structured, high-accountability environments.
• Proven success in B2B sales.
• Strong communication skills and situational awareness.
• Be coachable, dependable, and mentally tough.
• Comfort operating independently while following established systems.
• Ability to perform in fast-paced, goal-driven conditions.
• Discipline, adaptability, and execution are critical for success.

Nice To Haves

• Leadership or training experience.

Responsibilities

• Conduct face-to-face B2B sales professionally and precisely.
• 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.
• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed