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

Licensing assistance

Comprehensive training

Job summary

Devine Business Group in Bend, Oregon seeks an Insurance Sales Representative and Trainer to blend field sales with hands-on coaching for local businesses. The role emphasizes service, impact, and meaningful relationships while helping teams grow.

You will work as an independent contractor with a base draw, uncapped commissions, and bonuses, plus comprehensive training and licensing support to advance your career and positively impact the community.

Qualifications

• Four+ years of sales or trainer experience required.
• Experience as coach, educator, or mentor a plus.

Responsibilities

• Sell high-value supplemental insurance to employers.
• Train and mentor future sales talent in the field.
• Operate as an independent contractor while building B2B relationships.

Skills

Sales experience

Training and mentoring

Coaching

Tools

CRM access

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.

To learn more about who we are and what we do, visit www.thedevinebusinessgroup.com

If you are ready to combine your passion for teaching, service, and personal achievement in a role that rewards your efforts and values your heart, we invite you to join Devine Business Group