Outside Sales Leader & Trainer – Flexible Hours & Growth

True North Group LLC.; Liberty (MO); Hybrid; USD 60,000 - 90,000; Full time

Benefits offered by this job

Leadership Training

Weekly Draw Pay

Performance-Based Incentives

Career Advancement

Collaborative Culture

Flexible Hours

Job summary

True North Group LLC is seeking an Outside Sales Representative and Trainer in Liberty, MO. The role blends field sales with leadership duties, including coaching new agents and expanding your own client base, with weekly activities centered on relationship-building and tailored insurance solutions.

You will lead by example, train others, and drive growth in a fast-paced, field-based environment, partnering with business owners and employee groups to deliver compelling benefit presentations.

Qualifications

• Proven experience in outside sales or business-to-business sales.
• Experience mentoring, coaching, or training others in a sales setting.
• Ability to present clearly and confidently—whether 1-on-1 or to a room of 50+.
• Strong organizational skills, follow-through, and CRM usage.
• A desire to serve, support, and grow those around you.
• Health & Life general lines license, or ability to obtain one within 90 days (we'll help with this process).

Responsibilities

• Meeting with business owners to understand their needs and offer tailored insurance plans.
• Delivering engaging benefit presentations to employee groups.
• Following up with clients and supporting them through claims and coverage questions.
• Shadowing new reps in the field and providing hands‑on sales training.
• Running call reviews, prep sessions, and debriefs with new team members.
• Helping new reps track progress and set weekly activity goals.
• Collaborating with your manager to build a strong, successful sales team.
• Maintaining and growing your own book of business while guiding others to do the same.

Skills

Outside sales

Mentoring

Presentation skills

CRM usage

Leadership

Customer relations

Education

Bachelor's degree or equivalent

Tools

Salesforce

Job description

True North Group LLC is seeking an Outside Sales Representative and Trainer in Liberty, MO. The role blends field sales with leadership duties, including coaching new agents and expanding your own client base, with weekly activities centered on relationship-building and tailored insurance solutions.

You will lead by example, train others, and drive growth in a fast-paced, field-based environment, partnering with business owners and employee groups to deliver compelling benefit presentations.