Field Sales Trainer & Leadership Coach — Uncapped Commission

True North Group; Portland (OR); On-site; USD 55,000 - 109,000; Full time

Benefits offered by this job

Uncapped commissions

Weekly draw pay

Leadership development

Job summary

True North Group in Portland, OR is seeking an Experienced Outside Sales Trainer who can develop new agents through ride-alongs, field training, and hands-on guidance. This role blends coaching with hands-on field leadership to help reps excel in insurance product demonstrations.

You will balance personal production with mentoring, foster a growth-focused culture, and leverage licensure in life & health insurance (or pursue licensure with company support).

Qualifications

• Sales experience with a background in training or leadership preferred.
• Strong communicator who enjoys coaching and motivating others.
• Team-oriented mindset focused on collective success.
• Licensed (or willing to obtain) life & health insurance license; licensure reimbursed by the company.

Responsibilities

• 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.

Skills

Sales experience

Training

Leadership

Communication

Teamwork

Organization

Coaching

Education

Life & Health Insurance License (or willingness to obtain)

Job description

True North Group in Portland, OR is seeking an Experienced Outside Sales Trainer who can develop new agents through ride-alongs, field training, and hands-on guidance. This role blends coaching with hands-on field leadership to help reps excel in insurance product demonstrations.

You will balance personal production with mentoring, foster a growth-focused culture, and leverage licensure in life & health insurance (or pursue licensure with company support).