Direct Sales Leader

True North Group LLC.; Ashland (KY); On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Leadership training

Weekly draw pay

Performance incentives

Career progression

Supportive culture

Flexible hours

Job summary

True North Group is seeking a Direct Sales Leader to drive growth in a territory-based sales program. You will balance field activities with leadership, coaching new representatives, guiding benefit presentations, and closing deals with integrity.

You’ll mentor a growing team, set goals, track performance, and partner with clients on claims and renewals, while enjoying a structured path to leadership and earnings potential.

Qualifications

• Sales experience in field or B2B settings.
• Leadership mindset with mentoring experience.
• Clear, concise communication across individuals and groups.
• Organized, reliable, dependable in following through.
• Integrity-driven service with client and team focus.
• Licensed health & life general lines or willingness to obtain within 90 days.

Responsibilities

• Meet with business owners and decision-makers to present benefits.
• Shadow and coach new agents in the field.
• Host regular team check-ins and track progress.
• Set monthly personal and team goals and report on activities.
• Support client relationships through claims, renewals, and questions.

Skills

Sales Experience

Leadership Mindset

Clear Communicator

Organized & Reliable

Service-Driven

Licensed or License-Ready

Education

Bachelor's degree

Tools

Salesforce

Job description

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.

Let’s lead the way forward,together!