On-Call Independent Contractor- Trainer

About the role

The Lead Trainer – Train-the-Trainer Program is an on-call independent contractor position designed to help build safer, more capable transportation organizations by developing the next generation of driver trainers. This role involves delivering high-quality Train-the-Trainer certification programs that equip instructors with the necessary knowledge and practical driving expertise.

Responsibilities

• Deliver engaging classroom and practical Train-the-Trainer certification programs that consistently meet Descartes training standards and receive positive participant feedback.
• Certify qualified trainer candidates by objectively evaluating classroom, behind-the-wheel, and closed-course performance while maintaining consistent assessment standards.
• Ensure 100% completion and accuracy of all required training records, participant documentation, liability waivers, and certification results following each training event.
• Maintain a safe learning environment by demonstrating and enforcing professional driving, backing, parking, and defensive driving practices throughout all classroom and field exercises.
• Travel to assigned training locations and independently manage training logistics, rental vehicles, materials, and expense reporting in accordance with company requirements.
• Represent Descartes professionally by delivering a consistent learning experience that reflects our commitment to safety, operational excellence, and customer service.

Qualifications

• Minimum two years of experience in commercial driver training, transportation safety, fleet operations, or a related field.
• Valid driver's license with an acceptable driving record.
• Ability to travel extensively throughout the Continental United States.
• Ability to independently coordinate rental vehicles and travel logistics.
• Ability to work flexible schedules, including weekdays and weekends, based on training demand.

Skills & Competencies

• Experience delivering commercial driver, transportation safety, or fleet operations training.
• Strong classroom facilitation and presentation skills using PowerPoint, Google Slides, or similar presentation tools.
• Ability to coach and develop adult learners through both classroom instruction and hands-on practical exercises.
• Strong knowledge of professional driving techniques, professional parking and backing techniques, defensive driving principles, DOT regulations, CSA compliance, and coaching and leadership principles.
• Experience conducting behind-the-wheel evaluations on public roadways.
• Ability to safely demonstrate and evaluate backing maneuvers and cone-based obstacle courses including serpentine, offset alley backing, dock backing, and other prescribed exercises.
• Strong documentation, organization, and administrative skills with the ability to accurately maintain electronic training records.
• Comfortable using Microsoft Office, Google Workspace, and company training applications.

Physical Requirements

• Ability to stand, walk, and instruct for extended periods.
• Ability to work outdoors in varying weather conditions.
• Ability to repeatedly enter and exit commercial vehicles.
• Ability to move, place, and retrieve training cones and equipment.
• Ability to demonstrate vehicle maneuvering and backing techniques throughout the training day.

Culture Add: TEAM Values

We value team members who communicate with transparency, share information openly, and build trust across functions. You bring excellence and expertise to your craft, hold a high bar for quality, and continuously improve your skills. You demonstrate accountability by owning outcomes, following through on commitments, and taking responsibility for results. You are driven by metrics, using data and measurable outcomes to continuously improve training quality and learner success.

What's in It for You

• $400 per training day, plus applicable per diem for approved training assignments.
• $400 for eligible travel days when travel exceeds 120 miles from your home to the training location.
• Additional eligible travel day compensation when traveling between qualifying training locations.
• Contractor workdays typically range from 8–12 hours depending on the training schedule and travel requirements.
• Training assignments may occur any day of the week, including weekends.

Compensation

• $400 per training day, plus applicable per diem for approved training assignments.
• $400 for eligible travel days when travel exceeds 120 miles from your home to the training location.
• Additional eligible travel day compensation when traveling between qualifying training locations.
• Contractor workdays typically range from 8–12 hours depending on the training schedule and travel requirements.
• Training assignments may occur any day of the week, including weekends.

Equipment

• Laptop computer
• HDMI cable
• Reliable internet access when required
• Ability to present using PowerPoint or Google Slides
• Ability to access company-provided training systems

Travel

• This position requires frequent travel throughout the Continental United States. Overnight travel is common depending on assignment locations. Rental vehicles are provided for approved business travel; personal vehicles are not required for training assignments.

Current Priority Coverage Areas

• Seattle, WA / Oregon / Northern California
• Idaho / Utah / Wyoming
• Albuquerque, NM
• Lubbock / Northern Texas
• St. Louis, MO
• Memphis, TN / Jackson, MS
• Tallahassee / Jacksonville, FL
• Lexington / Louisville, KY
• Roanoke / Richmond, VA
• Syracuse, NY
• Philadelphia, PA