Outside Sales Representative and Trainer
Location: Medford, Oregon, United States
Company: True North Group LLC.
Job Type: Full-time
Posted: Feb 10, 2026
Application deadline: Apr 12, 2026
Source: ZipRecruiter
Join Our Team at True North Group!
Position: Outside Sales Representative and Trainer
Number of Openings: 1 Territory Leadership Position Available
About Us
At True North Group, we do more than offer supplemental insurancewe 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 anOutside 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 weekselling 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 theirscoaching, role-playing, and troubleshooting along the way. This is a dynamic, boots-on-the-ground leadership role with plenty of room to grow.
What We're Looking For
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 confidentlywhether 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)
Position Overview
This is a hybrid role combining outside sales and field leadership. Weekly responsibilities include:
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
We Offer
Leadership Training: Hands-on support to grow your leadership skills and train effectively in the field
Weekly Draw Pay: Reliable income with bonuses and commissions starting on day one
Performance-Based Incentives: Quarterly and annual trips, cash bonuses, stock share awards, and lifetime-vested renewal commissions
Career Advancement: Clear paths into senior leadership, regional expansion, or training roles as you develop
Collaborative Culture: A team that celebrates wins, shares knowledge, and grows together
Flexible Hours: Build your schedule around client needs and your team's availability
Additional Qualifications
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
Lead from the Front
If you're ready to grow your career while guiding others toward success, this is your chance to make a lasting impact. At True North Group, you won't just lead a teamyou'll help shape the future of our company.
Apply now and start building something meaningful.
https://www.thetruenorthgroupllc.com
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