Outside Sales Representative and Trainer

Devine Business Group; Medford (OR); On-site; USD 85,000 - 95,000; Full time

Benefits offered by this job

Weekly draw pay

Uncapped commissions & bonuses

Mentorship & training

Job summary

Devine Business Group is seeking an ambitious Sales Representative & Trainer to join as an independent contractor. You will build relationships, close deals, and mentor new teammates while earning uncapped commissions and weekly draw pay.

This role involves in-person, business-to-business engagements with a strong earnings potential and growth opportunities through hands-on mentorship and leadership.

Qualifications

• 5+ years of professional work experience (post-high school).
• Willingness to obtain a state health insurance license (licensing assistance and reimbursement provided).
• Strong communication, presentation, and relationship-building skills.
• Self-motivated and confident in a performance-based role.

Responsibilities

• Build and grow meaningful relationships with local business owners and decision-makers
• Present tailored supplemental insurance solutions that protect and empower clients
• Mentor and train new team members, providing guidance, coaching, and support
• Track performance, meet or exceed goals, and use feedback to improve strategies
• Lead by example, creating a culture of professionalism, focus, and results

Skills

Communication skills

Presentation skills

Relationship-building

Self-motivation

5+ years experience

Licensing commitment

Job description

Outside Sales Representative and Trainer – Lead, Sell, and Empower Others

Position Overview

Devine Business Group is seeking an ambitious, driven, and people-focused Sales Representative & Trainer to join our team. In this direct sales role as an independent contractor, you'll not only build lasting relationships and close deals but also mentor and train new team members, sharing your knowledge and helping them succeed.

This isn't a desk job—it's a career designed for someone who thrives on recognition, growth, and achievement. With uncapped earning potential, the harder you push, the more you'll be rewarded. Our weekly draw pay ensures stability as you launch, while hands-on mentorship and training give you the tools to shine.

Job Details:

• Compensation: $85,000–$95,000 per year (weekly draw pay, uncapped commissions & bonuses)
• Schedule: Monday–Friday, weekends as needed
• Location: Business-to-business, in-person

About Us

At Devine Business Group, we believe success comes from drive, service, and connection. Our team is made up of passionate professionals who value hard work, integrity, and growth—both individually and together. We're not just building sales careers; we're building leaders who empower others while making a difference in their communities.

What You'll Do

• Build and grow meaningful relationships with local business owners and decision-makers
• Present tailored supplemental insurance solutions that protect and empower clients
• Mentor and train new team members, providing guidance, coaching, and support
• Track performance, meet or exceed goals, and use feedback to improve strategies
• Lead by example, creating a culture of professionalism, focus, and results

Who Thrives Here

• Ambitious Achievers: You set big goals and love being recognized for reaching them
• People-Centered Leaders: You enjoy building trust, networking, and helping others succeed
• Driven & Disciplined Performers: You stay focused, consistent, and energized by performance-based rewards
• Mentor & Coach: You take pride in developing others while continuing to grow personally and professionally

Qualifications

• Strong communication, presentation, and relationship-building skills
• Self-motivated and confident in a performance-based role
• 5+ years of professional work experience (post-high school)
• Willingness to obtain a state health insurance license (licensing assistance and reimbursement provided)

What We Offer

• Earnings Potential: $85,000 - $95,000+ annually with draw pay, bonuses, and uncapped commissions
• Career Development: Hands-on training, mentorship, and leadership growth opportunities
  Recognition & Incentives: Trips, cash bonuses, stock options, and more for top performers
• Flexibility & Autonomy: Manage your own time and territory while being backed by a supportive team

To learn more about Devine Business Group visit: http://www.thedevinebusinessgroup.com