Outside Sales Representative and Trainer

True North Group.•Vancouver, WA

16h•Hybrid

About The Position

At True North Group, we do more than offer supplemental insurance—we empower people. We partner with small and mid-sized businesses to provide benefit solutions that protect what matters most: their employees and families. But just as importantly, we invest in our own team. If you have a passion for helping others succeed, leading by example, and building strong client relationships, we want you on our side as an Outside Sales Representative and Trainer. The Role As an Outside Sales Representative and Trainer, you'll be a cornerstone of our team in your local territory. You'll be out in the field each week—selling to business owners, presenting to groups of employees, and training new agents as they begin their careers. Your role is part mentor, part high-performing sales representative, and fully invested in both personal and team success. You'll lead from the front by building your own client base, then guide others as they build theirs—coaching, role-playing, and troubleshooting along the way. This is a dynamic, boots-on-the-ground leadership role with plenty of room to grow.

Requirements

Proven experience in outside sales or business-to-business sales
Experience mentoring, coaching, or training others in a sales setting
Ability to present clearly and confidently—whether 1-on-1 or to a room of 50+
Strong organizational skills, follow-through, and CRM usage
A desire to serve, support, and grow those around you
A Health & Life general lines license, or the ability to obtain one within 90 days (we'll help with this process)

Nice To Haves

Bachelor's degree or equivalent experience in sales, leadership, or coaching
Experience using CRM software (we use Salesforce)
A coachable, positive attitude and a desire to help others win
Strong time management and communication skills

Responsibilities

Meeting with business owners to understand their needs and offer tailored insurance plans
Delivering engaging benefit presentations to employee groups
Following up with clients and supporting them through claims and coverage questions
Shadowing new reps in the field and providing hands-on sales training
Running call reviews, prep sessions, and debriefs with new team members
Helping new reps track progress and set weekly activity goals
Collaborating with your manager to build a strong, successful sales team
Maintaining and growing your own book of business while guiding others to do the same