Field Sales Agent and Trainer

True North Group LLC.; Gillette (WY); On-site; USD 50,000 - 90,000; Full time

Benefits offered by this job

Weekly draw pay

Bonuses

Stock options

Advanced leadership development

Incentive trips

Job summary

True North Group LLC is seeking a Field Sales Agent and Trainer to drive sales while developing a high-performing team. You will coach, mentor, and scale success, helping new representatives reach goals and deliver protection to families and workers in your community.

This role focuses on leading from the front, training others, and building a scalable agency. Licensing in Health & Life is encouraged, with reimbursement if needed, and opportunities for rapid leadership advancement.

Qualifications

• Experience in outside sales or field-based roles.
• Ability to coach, mentor, and develop new hires.
• Strong communication and presentation skills.
• Currently licensed in Health & Life or willing to obtain within 90 days with company reimbursement.

Responsibilities

• Conduct in-person appointments with business owners and employees.
• Model high-performance sales behavior for new team members.
• Mentor new hires through onboarding and field training.
• Support sales representatives with product knowledge and systems.
• Lead daily or weekly team huddles to align goals.
• Track production and forecast activity with leadership.

Skills

Outside sales

Team leadership

Coaching / training

Effective communication

Health & Life license

Job description

Join Our Team at True North Group!

Position Title: Field Sales Agent and Trainer

Number of Openings: 1 Territory Leadership Position Available

At True North Group, we believe leadership isn't about a title. It's about action, integrity, and raising others up. We're expanding fast, and we're looking for leaders who want to make an impact, not just earn a paycheck.

As a Field Sales Agent and Trainer, you'll do more than just sell. You'll coach, mentor, and scale success. You'll be on the front lines helping new representatives hit goals, build confidence, and deliver critical protection to families and workers in your community.

This is an ideal role for someone with sales experience who's ready to move into mentorship and team development.

What You'll Be Doing

Your mission is twofold. Drive production and build people while providing our supplemental insurance benefits to small and medium sized businesses.

Your responsibilities will include:

• Running in-person appointments with business owners and employees
• Modeling high-performance sales behavior for new team members
• Mentoring new hires through onboarding and field training
• Supporting sales representatives with product knowledge and systems
• Leading daily or weekly team huddles to align goals
• Tracking production, forecasting activity, and collaborating with leadership

You won't be in this alone—you'll have top-tier mentorship and leadership support as you build your own team.

What You'll Get

At True North, we reward performance with leadership opportunities and growth incentives.

You can expect:

• Weekly Draw Pay, Bonuses, and Stock Options
• Advanced Leadership and Coaching Development
• Incentive Trips, Contests and Weekly Recognition
• Fast-Track Growth into Agency Ownership
• A Collaborative Culture Focused on Impact & Integrity

What You Bring to the Table

We're looking for someone who leads from the front, thrives under pressure, and finds fulfillment in helping others succeed.

Our ideal candidate is:

• A confident communicator who can coach and train others
• Organized, consistent, and dependable
• Goal-oriented, with a strong internal drive
• Experienced in outside sales or team leadership
• Passionate about making a difference and growing a team
• Currently licensed, or willing to get licensed (Health & Life) within your first 90 days—we reimburse the fees and support your preparation.

Bonus Points If You've Got:

• Experience mentoring or onboarding new hires
• Background in direct sales, athletics, or entrepreneurship
• A desire to eventually lead your own team or agency

This Is Your Next Chapter

This role isn't about managing from the sidelines—it's about leading from the trenches, building others up, and becoming the kind of leader you wish you had.

www.thetruenorthgroupllc.com