Insurance Sales Representative and Trainer

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

Benefits offered by this job

CRM access

State licensing assistance

Commission-based earnings

Training provided

Job summary

Devine Business Group is seeking a driven Insurance Sales Representative and Trainer to operate as an independent contractor, going business-to-business to introduce employers to high-value supplemental insurance benefits. The role includes coaching and mentoring future sales talent.

You will develop meaningful client relationships, work within a close-knit team, and help protect families and businesses while delivering exceptional service and leading by example.

Qualifications

• At least four years of work experience in sales or training.
• Experience as coach, educator, or mentor preferred.
• Ability to work independently and in a team.

Responsibilities

• Operate as an independent contractor in a direct sales and field trainer role.
• Visit employers to present high-value supplemental insurance benefits.
• Develop future sales talent through coaching in the field.
• Meet performance-based targets and participate in training.

Skills

Sales experience

Coaching / Mentorship

Independent worker

Relationship-building

Training skills

Tools

CRM software

Job description

Insurance Sales Representative and Trainer

At Devine Business Group, we believe that sales is not just about numbers—it is about service, impact, and meaningful relationships. We are seeking driven and compassionate professionals who want to bring high-quality insurance benefits to local businesses while helping others grow and thrive.

If you are a natural encourager with a strong sense of purpose, who finds fulfillment in helping others succeed and creating positive change, we want to hear from you.

Who You Are

You are a dedicated professional with at least four years of work experience and a track record of excellence in sales or training. You may have experience as a coach, educator, or mentor, and you value the opportunity to guide others toward success. You are motivated to serve with integrity and deliver the highest standard of care to the people around you. You enjoy working independently but are energized by being part of a close-knit team.

You are someone who:

• Thrives on meaningful connections and community engagement

• Has experience in or a passion for coaching and mentorship

• Believes in leading by example and uplifting others

• Wants to make a significant impact through service-oriented work

What You’ll Do

As a direct sales representative and field trainer, you will operate as an independent contractor, going business-to-business to introduce employers to high-value supplemental insurance benefits that support their teams and strengthen their organizations. In this role, you will also help develop future sales talent, serving as a coach and mentor in the field.

What We Offer

• Full-time position. Flexible Monday to Friday schedule with occasional weekends

• Base draw, uncapped commissions, and regular bonuses (earn $85,000–$95,000 performance-based compensation)

• Comprehensive training in the field and classroom, plus CRM access

• State licensing assistance with reimbursement of state fees after certain metrics are met

• Supportive team culture focused on collaboration, growth, and leadership development and opportunity to make a positive community impact

The Impact

This role is ideal for those who want more than a job—they want a mission. You'll help protect families and businesses, support your team's growth, and serve your community with compassion and excellence.