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Position Title: Direct Sales Leader
Open Role: 1 Leadership Opportunity Available in Territory-Based Sales
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.
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.
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.
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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).
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.
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!
Supplemental insurance agency providing business-to-business insurance solutions.
Visit company websiteJobs and hiring trendsUSD 90000-110000 yearly / year
Full-time
Mid · 4+ years experience
Onsite
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