Territory Outside Sales Leader & Trainer

True North Group; Midland (TX); 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 is seeking an Outside Sales Representative and Trainer to lead in your local territory. You will sell to business owners, present to employee groups, and train new agents as they start their careers.

This hybrid role combines field sales with leadership duties, including coaching, role-playing, and helping reps grow their books of business. Strong communication and CRM skills, plus a Health & Life license or the ability to obtain one within 90 days, are valued.

Qualifications

• Outside sales or B2B sales experience.
• Experience mentoring, coaching, or training others in a sales setting.
• Ability to present clearly and confidently—1-on-1 or to groups of 50+.
• Strong organizational skills, follow-through, and CRM usage.

Responsibilities

• Meet with business owners to understand needs and offer tailored insurance plans.
• Deliver engaging benefit presentations to employee groups.
• Follow up with clients and support them through claims and coverage questions.
• Shadow new reps in the field and provide hands-on sales training.
• Run call reviews, prep sessions, and debriefs with new team members.
• Help new reps track progress and set weekly activity goals.
• Collaborate with your manager to build a strong, successful sales team.
• Maintain and grow your own book of business while guiding others to do the same.

Skills

Outside sales

Mentoring / coaching

Presentation

CRM usage

Education

Bachelor's degree or equivalent experience

Tools

Salesforce

Job description

True North Group is seeking an Outside Sales Representative and Trainer to lead in your local territory. You will sell to business owners, present to employee groups, and train new agents as they start their careers.

This hybrid role combines field sales with leadership duties, including coaching, role-playing, and helping reps grow their books of business. Strong communication and CRM skills, plus a Health & Life license or the ability to obtain one within 90 days, are valued.