Field Sales Leader & Trainer (Hybrid Role)

True North Group LLC.; Saint Augustine (FL); Hybrid; USD 70,000 - 120,000; 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 client development in your local territory and coach new agents as they begin their careers.

This hybrid role blends field sales with leadership training, mentorship, and ongoing coaching, with a focus on building a high-performing team and growing your own book of business. You’ll train, coach, and guide others while meeting with business owners and delivering compelling presentations.

Qualifications

• Experience in outside/business-to-business sales.
• Experience mentoring or training in a sales setting.
• Ability to present clearly to individuals or groups.
• Strong organizational skills and CRM usage.

Responsibilities

• Meet with business owners to assess needs and offer tailored insurance plans.
• Deliver benefit presentations to employee groups.
• Support clients through claims and coverage questions.
• Shadow and train new sales representatives in the field.
• Lead call reviews and weekly activity planning with the team.
• Collaborate with manager to build and grow the sales team.
• Grow personal book of business while guiding others to do the same.

Skills

Outside sales

Coaching/Training

CRM usage

Communication

Leadership

Presentations

Education

Bachelor's degree or equivalent experience in sales/leadership

Tools

Salesforce CRM

Job description

True North Group LLC. is seeking an Outside Sales Representative and Trainer to lead client development in your local territory and coach new agents as they begin their careers.

This hybrid role blends field sales with leadership training, mentorship, and ongoing coaching, with a focus on building a high-performing team and growing your own book of business. You’ll train, coach, and guide others while meeting with business owners and delivering compelling presentations.