Outside Sales Representative and Trainer

Job DescriptionJob Description 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 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. 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 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) Position Overview 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 team—you'll help shape the future of our company. #J-18808-Ljbffr True North Group LLC.