True North Group LLC.

Engage with local businesses and individuals to promote and sell supplemental insurance plans, build relationships, and support clients. | High school diploma, strong communication and organizational skills, willingness to obtain a health & life license, and basic digital tool proficiency. | Join Our Team at True North Group Position: Sales Representative, Entry-Level Number of Openings: 1 Territory Sales Position Available About Us At True North Group, we believe great careers are built on real relationships. We're a people-first supplemental insurance agency focused on helping small and mid-sized businesses protect what matters most: their families and employees. Whether you're just starting your professional journey or looking for a fresh start, this entry-level sales opportunity is the perfect launchpad. We'll give you the training, tools, and support to succeedno prior insurance experience needed. The Role As an Entry-Level Sales Representative, you'll get to know local businesses in your territory, learn about their employee benefit needs, and offer supplemental insurance plans that make a difference. You'll have the freedom to create your own schedule and work in a way that fits your clients' availabilitywhile being backed by a proven system and a supportive team. Your job isn't just about making salesit's about making connections. You'll build trust, provide guidance, and become a valuable resource to the business owners and employees you serve. What We're Looking For A people-person who enjoys conversation and building relationships Someone who's motivated, self-driven, and ready to learn Great communicatorboth one-on-one and in front of a group Strong organizational habits and attention to follow-up A genuine desire to help others and make a positive impact Willingness to obtain a Health & Life general lines license within 90 days (we'll help cover the cost later and provide study support) Position Overview This is an outside sales role, where you'll work locally in your own territory. You'll be trained to: Visit businesses and introduce our supplemental insurance offerings Meet with business owners and present to groups of employees (often 1050+ at a time) Respond to client questions via phone and email Set appointments, conduct follow-ups, and support clients through claims Use our Salesforce CRM to track your activities, contacts, and progress Work closely with your manager to set and meet sales goals Build your own client base and develop long-term relationships Share your weekly schedule and results with your manager We Offer Thorough Training: Get up to speed with both online and in-the-field coaching Weekly Draw Pay: Steady income as you build your book of business, with bonuses and commissions available from day one Exciting Incentives: Quarterly trips, cash bonuses, stock share awards, and lifetime-vested renewal commissions Career Advancement: Clear pathways to grow into leadership, training, or higher-level sales roles based on your performance Continued Development: Ongoing support to help you grow your skills and your confidence Flexible Hours: You'll have the freedom to design your workday around your business clients' availability Additional Qualifications High school diploma required; a bachelor's degree or customer service experience is a plus Strong work ethic and willingness to learn new skills Comfortable using basic digital tools (email, calendar, CRM systems) Already licensed in Health & Life, or ready to get licensed within 90 days Start Your Career with Purpose If you're ready to start a career that's flexible, meaningful, and full of opportunity, we'd love to meet you. At True North Group, we'll help you build something you can be proud ofone client and one conversation at a time. Apply now and begin your journey with us today. https://www.thetruenorthgroupllc.com

Leading and mentoring a sales team, developing client relationships, and achieving sales targets. | Experience in sales, leadership or mentoring skills, and a license or willingness to obtain a license within 90 days. | Join Our Team at True North Group! Position Title: Direct Sales Leader Open Role: 1 Leadership Opportunity Available in Territory-Based Sales About Us At True North Group, we're committed to more than just offering supplemental insurance. We work directly with small and mid-sized companies to protect what matters most: their people. If you're passionate about helping others grow and have a talent for both selling and mentoring, we invite you to step into a leadership role with us. The Role: As a Direct Sales Leader, you'll be a representative helping businesses navigate their benefit needs, while also serving as a coach and mentor, developing new talent within your territory. You'll set the pace by example, teaching others how to prospect, present, and close with integrity. This role blends independent field work with meaningful leadership responsibilities. You'll guide new representatives through their first policies and presentations, helping them build confidence and consistency. Your success will come not just from what you achieve, but from what your team becomes under your guidance. What We're Looking For Sales Experience: You've had success in sales particularly in a field or B2B setting and understand the importance of preparation, relationship-building, and follow-through. Leadership Mindset: Whether you've led teams formally or simply mentored others along the way, you enjoy watching people grow and succeed. Clear Communicator: You can explain complex ideas simply, both one-on-one and to a group. Organized and Reliable: You follow through, track activity, and keep commitments both to clients and your team. Service-Driven: You put people first, and it shows in how you coach, how you sell, and how you lead. Licensed or License-Ready: You hold a Health & Life general lines license, or you're willing to earn it within 90 days (we'll help cover the cost and guide you through the process). What You'll Be Doing This is a field-based role with leadership responsibilities, and each week may include Personal Sales Activities: Meeting with business owners and decision-makers, giving benefit presentations to their teams, following up on leads, and setting appointments. Training & Mentoring: Shadowing new agents in the field, role-playing sales scenarios, helping others navigate their first few weeks and close their first deals. Team Development: Hosting regular check-ins, helping teammates track progress, and creating a positive, winning team culture. Goal Setting & Reporting: Working with your manager to set personal and team goals each month, and tracking key sales activities across your territory. Supporting Client Relationships: Helping both your clients and those of your team navigate claims, renewals, and benefit questions. What We Offer Hands-On Leadership Training: Tools and guidance to help you develop as both a high-performing representative and a trusted team leader. Weekly Draw Pay: A stable income base to get started, plus immediate eligibility for commission and bonuses. Performance Incentives: Quarterly retreats, annual incentive trips, stock share bonuses, and lifetime-vested renewal commissions. Career Pathways: We promote from within, team leaders can advance based on their performance to higher positions, and with larger teams. Supportive Culture: You won't do it alone. We back our leaders with strong mentorship, systems, and recognition for excellence. Flexible Hours: As you build your team and book of business, your schedule becomes more self-directed. Additional Qualifications Education: A bachelor's degree is preferred, but we'll also consider candidates with four or more years of experience in a customer-facing or sales environment. Tech Savvy: You're comfortable learning new softwareSalesforce and other digital tools come naturally to you. Driven and Positive: You bring energy and focus to every day and help your team do the same. Integrity and Ownership: You lead by example and take responsibility for your own success and the culture of your team. Your Next Step Starts Here At True North Group, we're growing fast and we're looking for leaders who want to build something meaningful. If you're ready to mentor others while advancing your own career, apply today. Your leadership can help shape the next generation of trusted advisors in our company. Learn more and apply at: https://www.thetruenorthgroupllc.com Let's lead the way forward,together!