Direct Sales Leader

True North Group.•Eugene, OR

19h•Onsite

About The Position

True North Group is hiring a Direct Sales Leader for a territory-based sales role combining independent field work with leadership responsibilities. The role represents the company to small and mid-sized businesses, helping them navigate benefit needs while coaching and mentoring new representatives. The leader demonstrates prospecting, presenting, and closing with integrity, and helps new team members build confidence and consistency as they develop their sales skills. The position includes personal sales activity, agent training and mentoring, team development, goal setting and reporting, and support for client relationships. The role offers hands-on leadership training, weekly draw pay, eligibility for commissions and bonuses, performance incentives, career advancement opportunities, and a supportive culture. Hours become more self-directed as the leader builds a team and book of business.

Requirements

Successful sales experience, particularly in a field or B2B setting.
A leadership or mentoring mindset and interest in helping others grow.
Clear communication skills, including explaining complex ideas one-on-one and to groups.
Organization, reliability, follow-through, and the ability to track activity and keep commitments.
A service-driven approach to selling, coaching, and leadership.
A Health & Life general lines license, or willingness to earn it within 90 days.
Comfort learning software and using Salesforce and other digital tools.
Drive, positivity, integrity, and ownership of personal success and team culture.
A bachelor's degree is preferred, or at least four years of experience in a customer-facing or sales environment.

Nice To Haves

A bachelor's degree.
Formal team leadership experience.
Field or B2B sales experience.

Responsibilities

Meet with business owners and decision-makers, present benefits to their teams, follow up on leads, and set appointments.
Shadow new agents in the field, role-play sales scenarios, and help them through their first weeks and initial deals.
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 key sales activities across the territory.
Help clients and team members’ clients with claims, renewals, and benefit questions.
Lead by example while teaching representatives how to prospect, present, and close with integrity.

Benefits

Weekly draw pay as a stable income base.
Immediate eligibility for commission and bonuses.
Quarterly retreats.
Annual incentive trips.
Stock share bonuses.
Lifetime-vested renewal commissions.
Hands-on leadership training and guidance.
Career advancement opportunities and promotion from within.
Supportive mentorship, systems, and recognition for excellence.
Flexible, increasingly self-directed hours as the team and book of business grow.
The company will help cover the cost of obtaining the required license and guide candidates through the process.