Field Sales Leader & Trainer — Flexible Hours & Growth

True North Group LLC.; Walla Walla (WA); Hybrid; USD 60,000 - 110,000; Full time

Benefits offered by this job

Leadership Training

Weekly Draw Pay

Performance-Based Incentives

Career Advancement

Collaborative Culture

Flexible Hours

Job summary

True North Group LLC is seeking an Outside Sales Representative and Trainer to lead in your local territory, selling to business owners, presenting to employee groups, and training new agents.

This hybrid role combines field leadership with sales, offering mentorship, dynamic growth, and a path into regional leadership as you expand your client base and train the next generation of top performers.

Qualifications

• Proven experience in outside sales or B2B sales.
• Experience mentoring, coaching, or training others in a sales setting.
• Ability to present clearly—1-on-1 or to a room of 50+ attendees.
• Strong organizational skills and CRM usage.
• Health & Life license is preferred or the ability to obtain one within 90 days.

Responsibilities

• Meet with business owners to understand needs and offer tailored insurance plans.
• Deliver engaging benefit presentations to employee groups.
• Follow up with clients and assist with claims and coverage questions.
• Shadow and train new reps, providing hands-on sales coaching.
• Collaborate with the manager to build a strong, successful sales team.

Skills

Outside sales

Mentoring/Coaching

Public speaking

CRM usage

Leadership

Education

Bachelor's degree or equivalent experience in sales/leadership/coaching

Tools

Salesforce

Job description

True North Group LLC is seeking an Outside Sales Representative and Trainer to lead in your local territory, selling to business owners, presenting to employee groups, and training new agents.

This hybrid role combines field leadership with sales, offering mentorship, dynamic growth, and a path into regional leadership as you expand your client base and train the next generation of top performers.