Field Sales Trainer & Leadership Coach

True North Group; St. George (VT); On-site; USD 60,000 - 90,000; Full time

Job summary

True North Group is seeking an Experienced Outside Sales Trainer to develop and mentor a growing team of sales representatives in the field. You will lead ride-alongs, provide hands-on guidance, and deliver practical coaching to enhance confidence and consistency across the team.

The role emphasizes balancing personal sales activity with mentorship, driving a positive, team-first culture, and demonstrating B2B product demos for supplemental insurance offerings.

Qualifications

• 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.

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

Job description

True North Group is seeking an Experienced Outside Sales Trainer to develop and mentor a growing team of sales representatives in the field. You will lead ride-alongs, provide hands-on guidance, and deliver practical coaching to enhance confidence and consistency across the team.

The role emphasizes balancing personal sales activity with mentorship, driving a positive, team-first culture, and demonstrating B2B product demos for supplemental insurance offerings.