Outside Sales Representative and Trainer
Not Disclosed•Full-TimeOn-site
location_onWest Front Street, McCoy, Midland, Midland County, Texas, 79701, United States
About Us
At True North Group, we do more than offer supplemental insurance; we empower people. We partner with small and mid-sized businesses to provide benefit solutions that protect what matters most: their employees and families. We also invest deeply in our own team. If you have a passion for helping others succeed, leading by example, and building strong client relationships, we want you on our side.
About the Role
As an Outside Sales Representative and Trainer, you will be a cornerstone of our team in your local territory. This is a dynamic, boots-on-the-ground leadership role that combines high-performing sales with field mentorship. You will spend your weeks selling to business owners, presenting to groups of employees, and training new agents as they begin their careers.
You will lead from the front by building your own client base while guiding others to do the same. Your day-to-day involves coaching, role-playing, and troubleshooting alongside new reps. You will shadow them in the field, run call reviews and prep sessions, and help them track progress and set weekly activity goals. This position is fully invested in both personal success and the growth of the team.
Why This Role Matters
If you are ready to grow your career while guiding others toward success, this is your chance to make a lasting impact. At True North Group, you won't just lead a team; you will help shape the future of our company. We offer a collaborative culture that celebrates wins, shares knowledge, and grows together, with clear paths into senior leadership, regional expansion, or training roles as you develop.
How to Apply
If you are ready to build something meaningful, apply now to join our team. Visit our website at thetruenorthgroupllc.com for more information.
Work location
Work model: On-site
West Front Street, McCoy, Midland, Midland County, Texas, 79701, United States
Midland, Texas
Key Responsibilities
- check_circleMeet with business owners to understand needs and offer tailored insurance plans
- check_circleDeliver engaging benefit presentations to employee groups
- check_circleFollow up with clients and support them through claims and coverage questions
- check_circleShadow new reps in the field and provide hands-on sales training
- check_circleRun call reviews, prep sessions, and debriefs with new team members
- check_circleHelp new reps track progress and set weekly activity goals
- check_circleMaintain and grow own book of business while guiding others to do the same
- check_circleCollaborate with manager to build a strong, successful sales team
Requirements
- verifiedProven experience in outside sales or business-to-business sales
- verifiedExperience mentoring, coaching, or training others in a sales setting
- verifiedAbility to present clearly and confidently to 1-on-1 or 50+ people
- verifiedStrong organizational skills, follow-through, and CRM usage
- verifiedHealth & Life general lines license, or ability to obtain one within 90 days
- verifiedBachelor's degree or equivalent experience in sales, leadership, or coaching
- verifiedExperience using CRM software (Salesforce)
Nice to Have
Bachelor's degree or equivalent experience in sales, leadership, or coaching. Experience using CRM software (we use Salesforce). A coachable, positive attitude and a desire to help others win. Strong time management and communication skills.
Benefits & Perks
check_circleWeekly draw pay with bonuses and commissions starting on day onecheck_circleQuarterly and annual trips, cash bonuses, and stock share awardscheck_circleLifetime-vested renewal commissionscheck_circleHands-on leadership training and field training supportClear career advancement paths into senior leadership and training roles
Similar Job Opportunities
Skills, education and keywords
Skills: Outside Sales, Business-To-Business Sales, CRM, Salesforce, Health & Life General Lines License.
Education: Bachelor's degree or equivalent experience in sales, leadership, or coaching.
Frequently asked questions about Outside Sales Representative and Trainer at True North Inc.
What does a Outside Sales Representative and Trainer at True North Inc. do?expand_more
In this Outside Sales Representative and Trainer at True North Inc. role, you will 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; and shadow new reps in the field and provide hands-on sales training.
What are the requirements for this Outside Sales Representative and Trainer role?expand_more
To qualify for the Outside Sales Representative and Trainer at True North Inc. position, applicants should have: 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 to 1-on-1 or 50+ people; Strong organizational skills, follow-through, and CRM usage; Health & Life general lines license, or ability to obtain one within 90 days; and Bachelor's degree or equivalent experience in sales, leadership, or coaching.
Where is the Outside Sales Representative and Trainer role at True North Inc. located?expand_more
Outside Sales Representative and Trainer at True North Inc. is based in West Front Street, McCoy, Midland, Midland County, Texas, 79701, United States. This is a on-site role.
Is this Outside Sales Representative and Trainer job remote, hybrid, or on-site?expand_more
True North Inc. has listed this Outside Sales Representative and Trainer role as on-site.
How much experience is required for this Outside Sales Representative and Trainer role?expand_more
Candidates for Outside Sales Representative and Trainer at True North Inc. should have mid level.
What skills do you need for the Outside Sales Representative and Trainer role at True North Inc.?expand_more
Key skills for Outside Sales Representative and Trainer at True North Inc. include Outside Sales; Business-To-Business Sales; CRM; Salesforce; and Health & Life General Lines License.
What education is required for Outside Sales Representative and Trainer at True North Inc.?expand_more
Educational requirements for this role: Bachelor's degree or equivalent experience in sales, leadership, or coaching.
What category does the Outside Sales Representative and Trainer role belong to?expand_more
Outside Sales Representative and Trainer at True North Inc. is part of the sales job category on Recrutus.
About True North Inc.
True North Inc. operates as an independent advertising agency based in New York, NY, with additional operations in San Francisco. The firm specializes in delivering integrated creative, media, technology, and insights services to support diverse communication goals. By leveraging modern media consumption habits, the agency assists clients in connecting effectively with customers, donors, and broader audiences through engaging strategies tailored to an always-on environment. This approach ensures that marketing efforts remain relevant and impactful across various platforms within the advertising services sector.
Browse more roles: All True North Inc. jobs, sales jobs on Recrutus.