Outside Sales Representative and Trainer

Job Description Join Our Team at True North Group!Position: Outside Sales Representative and TrainerNumber of Openings: 1 Territory Leadership Position AvailableAbout UsAt 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 RoleAs 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 ForProven experience in outside sales or business-to-business salesExperience mentoring, coaching, or training others in a sales settingAbility to present clearly and confidentlywhether 1-on-1 or to a room of 50+Strong organizational skills, follow-through, and CRM usageA desire to serve, support, and grow those around youA Health & Life general lines license, or the ability to obtain one within 90 days (we'll help with this process)Position OverviewThis 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 plansDelivering engaging benefit presentations to employee groupsFollowing up with clients and supporting them through claims and coverage questionsShadowing new reps in the field and providing hands-on sales trainingRunning call reviews, prep sessions, and debriefs with new team membersHelping new reps track progress and set weekly activity goalsCollaborating with your manager to build a strong, successful sales teamMaintaining and growing your own book of business while guiding others to do the sameWe OfferLeadership Training: Hands-on support to grow your leadership skills and train effectively in the fieldWeekly Draw Pay: Reliable income with bonuses and commissions starting on day onePerformance-Based Incentives: Quarterly and annual trips, cash bonuses, stock share awards, and lifetime-vested renewal commissionsCareer Advancement: Clear paths into senior leadership, regional expansion, or training roles as you developCollaborative Culture: A team that celebrates wins, shares knowledge, and grows togetherFlexible Hours: Build your schedule around client needs and your team's availabilityAdditional QualificationsBachelor's degree or equivalent experience in sales, leadership, or coachingExperience using CRM software (we use Salesforce)A coachable, positive attitude and a desire to help others winStrong time management and communication skillsLead from the FrontIf 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