About the job
Join Our Team at True North Group!
Position: Outside Sales Representative and Trainer
Openings: 1 Territory Leadership Position Available
About Us
At True North Group, we go beyond providing supplemental insurance; we empower individuals and businesses alike. We collaborate with small to mid-sized companies to deliver benefit solutions that safeguard what matters most: their employees and families. Equally important, we prioritize the growth and success of our own team. If you're passionate about fostering success, leading by example, and cultivating robust client relationships, we invite you to become an Outside Sales Representative and Trainer with us.
The Role
As an Outside Sales Representative and Trainer, you will serve as a vital member of our local team. Your week will be spent in the field, selling to business owners, delivering engaging presentations to employee groups, and mentoring new agents as they embark on their careers. This role encompasses mentorship, high-level sales performance, and a commitment to both personal and team success.
You'll lead by example by developing your own client base while simultaneously guiding others through coaching, role-playing, and providing solutions. This dynamic, hands-on leadership position offers ample opportunities for growth.
What We Are Looking For
- Demonstrated experience in outside sales or business-to-business sales.
- Experience mentoring, coaching, or training others in a sales capacity.
- Exceptional presentation skills, whether one-on-one or to larger groups (up to 50+).
- Strong organizational skills, follow-through, and proficiency in CRM systems.
- A genuine desire to assist, support, and develop those around you.
- A Health & Life general lines license, or the capability to acquire one within 90 days (we will assist in this process).
Position Overview
This hybrid role merges outside sales with field leadership. Weekly responsibilities will include:
- Engaging with business owners to identify their needs and propose tailored insurance solutions.
- Delivering compelling benefit presentations to employee groups.
- Providing ongoing support to clients with claims and coverage inquiries.
- Shadowing new representatives in the field and delivering hands-on sales training.
- Conducting call reviews, preparation sessions, and debriefs with new team members.
- Assisting new representatives in tracking their progress and establishing weekly activity targets.
- Collaborating with your manager to foster a strong and successful sales team.
- Maintaining and expanding your own client portfolio while mentoring others to do the same.
We Offer
Leadership training: Hands-on support to enhance your leadership skills and train effective team members.

