Direct Sales Leader at The True North Group in Bend, OR

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 software—Salesforce 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!