Direct Sales Leader

True North Group. • Bellingham, WA

15h • Onsite

About The Position

True North Group is seeking a Direct Sales Leader to represent the company to small and mid-sized businesses, help them navigate their employee benefit needs, and develop new sales talent within a territory. The role combines independent, field-based sales work with coaching and team leadership. The leader demonstrates ethical sales practices while helping representatives learn to prospect, present, and close, and supports them through early policies and presentations.

The position includes meeting with business owners and decision-makers, presenting benefits to employee teams, following up on leads, and setting appointments. It also involves mentoring new agents in the field, conducting sales practice, supporting team progress and culture, setting and tracking goals with a manager, and helping clients with claims, renewals, and benefit questions. True North Group offers leadership training, weekly draw pay, commission and bonus eligibility, performance incentives, advancement opportunities, mentorship, and flexible hours as the team and book of business develop.

Requirements

• Successful sales experience, particularly in a field or B2B setting.
• A leadership mindset and interest in mentoring and developing others; formal leadership experience is not required.
• Clear communication skills, including explaining complex ideas to individuals and groups.
• Organization, reliability, follow-through, and the ability to track activity and keep commitments.
• A service-driven approach to selling, coaching, and leading.
• A Health & Life general lines license, or willingness to earn one within 90 days; the company will help cover the cost and guide the process.
• Comfort learning software and using digital tools such as Salesforce.
• A driven and positive approach, with integrity, ownership, and willingness to lead by example.
• A bachelor's degree is preferred, or at least four years of experience in a customer-facing or sales environment will also be considered.

Nice To Haves

• Bachelor's degree.
• Experience in field or B2B sales.
• Formal team leadership experience.

Responsibilities

• Meet with business owners and decision-makers, present benefits to their teams, follow up on leads, and set appointments.
• Shadow and train new agents in the field, role-play sales scenarios, and help them through their first weeks and initial sales.
• Host regular team check-ins, help teammates track progress, and foster a positive team culture.
• Work with a manager to set monthly personal and team goals and track sales activity across the territory.
• Help clients and team clients navigate claims, renewals, and benefit questions.

Benefits

• Hands-on leadership training and guidance.
• Weekly draw pay, with immediate eligibility for commissions and bonuses.
• Quarterly retreats.
• Annual incentive trips.
• Stock share bonuses.
• Lifetime-vested renewal commissions.
• Promotion from within and opportunities to advance to higher positions and lead larger teams.
• Mentorship, systems, and recognition for excellence.
• Flexible hours as the team and book of business develop.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed