Outside Sales Trainer

True North Group LLC.; Portland (OR); On-site; USD 60,000 - 95,000; Full time

Benefits offered by this job

Uncapped commission

Weekly draw pay

Performance incentives and bonuses

Leadership development

Clear advancement path

Retreats and incentive travel

Job summary

True North Group LLC in Portland, Oregon, seeks an Experienced Outside Sales Trainer to coach new agents through ride-alongs, field training, and hands-on guidance in selling supplemental insurance products.

This role blends leadership with active selling, promoting a team-focused culture and in-field mentorship. Licensure in life and health insurance is supported and reimbursed, with advancement opportunities and ongoing leadership development.

Qualifications

• Experience in sales with training or leadership background.
• Strong communication and coaching skills.
• Willingness to obtain life & health insurance licensure (company will reimburse).

Responsibilities

• Support new agents with ride-alongs, field training, and hands-on guidance.
• Provide practical coaching that builds confidence and consistency.
• Foster a positive, team-focused culture rooted in growth.
• Balance personal production with training and mentorship responsibilities.
• Provide business-to-business demonstrations for supplemental insurance products.

Skills

Sales experience

Training/Leadership

Coaching

Communication

Team orientation

Job description

Join Our Team at True North Group

Position: Experienced Outside Sales Trainer

Number of Openings: 1 Territory Representative Position Available

The Role

At True North Group, we believe great leaders don't just close sales — they build people. We're looking for an experienced trainer who is passionate about developing others, leading by example in the field, and helping new sales representatives find their footing.

If you find fulfillment in seeing others succeed and want to play a key role in shaping a growing team, this opportunity is built for you.

What You'll Be Doing:

• Supporting new agents with ride-alongs, field training, and hands-on guidance
• Providing practical coaching that builds confidence and consistency
• Encouraging a positive, team-focused culture rooted in growth
• Balancing personal production with training and mentorship responsibilities
• Providing business to business demonstrations for our supplemental insurance products

What You'll Get:

• Competitive uncapped commission, weekly draw pay, and performance incentives and bonuses
• Ongoing leadership development and mentorship from senior leaders
• A clear path for advancement in agency leadership
• Recognition events, retreats, and incentive travel opportunities
• The chance to make a lasting impact on both clients and teammates

What We're Looking For:

• Experience in sales, with a background in training or leadership preferred
• Strong communicator who enjoys coaching and motivating others
• Team-oriented mindset with a focus on collective success
• Reliable, organized, and willing to lead in the field
• Licensed (or willing to obtain) in life & health insurance, we will support you in obtaining licensure, and reimburse you after

Why This Matters

Families rely on us for protection during some of life's most difficult moments. By training and supporting new sales professionals, you help extend that protection to more people — while shaping the next generation of leaders.