Direct Sales Leader

True North Group.•Columbia, MO

1d•Onsite

About The Position

True North Group is hiring a Direct Sales Leader for a territory-based sales role combining personal sales activities with coaching and team leadership. The leader represents the company to small and mid-sized businesses, helps them understand benefit needs, and develops new representatives by modeling prospecting, presentations, and closing with integrity. The role includes independent field work and supporting agents as they build confidence, consistency, and their businesses. The position involves meeting business owners and decision-makers, presenting benefits to teams, following up on leads, and setting appointments. The leader also shadows and mentors new agents, hosts team check-ins, supports goal setting and activity reporting, and assists clients with claims, renewals, and benefit questions. True North Group offers hands-on leadership training, weekly draw pay, commission and bonus eligibility, performance incentives, career pathways, and mentorship. The schedule becomes more self-directed as the leader develops a team and book of business.

Requirements

Successful sales experience, particularly in a field or B2B setting.
Leadership or mentoring experience and an interest in helping others develop.
Clear communication skills, including the ability to explain complex ideas simply one-on-one and to groups.
Organization, reliability, follow-through, and commitment tracking.
A service-driven approach to coaching, selling, and leading.
A Health & Life general lines license, or willingness to earn it within 90 days.
Comfort learning software and digital tools.
Positive energy, focus, integrity, and ownership of personal performance and team culture.

Nice To Haves

A bachelor's degree.
Four or more years of experience in a customer-facing or sales environment may be considered as an alternative to a bachelor's degree.

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 and coach them through sales scenarios and their first weeks and 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 clients navigate claims, renewals, and benefit questions.

Benefits

Hands-on leadership training and guidance.
Weekly draw pay.
Immediate eligibility for commission and bonuses.
Quarterly retreats.
Annual incentive trips.
Stock share bonuses.
Lifetime-vested renewal commissions.
Promotion-from-within career pathways.
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 earning the required license.