On-Call Independent Contractor- Trainer

The Descartes Systems Group Inc.; Northern (KY); Hybrid; USD 74,000 - 166,000; Part time

Job summary

Descartes Systems Group Inc. seeks a Lead Trainer to deliver high-quality Train-the-Trainer certification programs across North America.

You will equip instructors with knowledge, coaching skills, and practical driving expertise to train professional drivers to the highest safety standards. The role requires experience in driver training, strong facilitation, and the ability to travel extensively, including weekends.

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.

Responsibilities

• Deliver engaging classroom and practical Train-the-Trainer certification programs that meet Descartes training standards.
• Certify qualified trainer candidates by evaluating classroom, behind-the-wheel, and closed-course performance.
• Maintain accurate training records, participant documentation, liability waivers, and certification results.

Skills

Driver training

Facilitation

Adult coaching

DOT regulations

CSA compliance

Coaching & leadership

Behind-the-wheel evaluation

Documentation

MS Office / Google Workspace

Tools

PowerPoint

Google Slides

Microsoft Office

Google Workspace

Job description

Descartes Unites the People and Technology that Move the World
The need for efficient, secure, and agile supply chains and logistics operations has become ever more critical and complex. By combining innovative technology, powerful trade intelligence and the reach of our network, Descartes helps get goods, information, transportation assets, and people where they’re needed, when they’re needed.

We’re one of the most broadly deployed logistics and supply chain technology companies in the world. More than 22,000 customers around the globe use our cloud-based solutions to transform the way they move inventory and information to enhance productivity, better serve customers, thrive competitively, keep pace with evolving regulations, and respond to rapidly changing market conditions. Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world. With record financial performance for more than 16 years, we lead the industry in innovation investment. Every day, logistics service providers, manufacturers, retailers, distributors, and other logistics-intensive businesses of all sizes rely on our scale, stability, and comprehensive solution footprint to move what’s most important to them. Learn more at www.descartes.com.

Lead Trainer – Train-the-Trainer Program (On-Call Independent Contractor)

Locations hired for: Nationwide (Travel Throughout the Continental United States)- 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

Engagement Type: On-Call Independent Contractor

Mission

Help build safer, more capable transportation organizations by developing the next generation of driver trainers. As a Lead Trainer, you will deliver high-quality Train-the-Trainer certification programs that equip instructors with the knowledge, coaching skills, and practical driving expertise needed to consistently train professional drivers to the highest safety standards.

Outcomes – What Success Looks Like

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

Skills & Competencies – How the Work Gets Done

Technical Expertise

• 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
  • 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.

Professional Requirements

• 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.

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, sharing information openly and building trust across functions. You bring excellence and expertise to your craft, holding a high bar for quality while continuously improving 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.

Aptitudes

• Smart: Able to understand & present professional safety techniques, assess candidate performance, and make sound instructional decisions.
• Curious: Continuously seeks better training methods, coaching techniques, and improvements in transportation safety.
• Coachable: Welcomes feedback, adapts instructional techniques, and continually develops as a professional trainer.

What’s in It for You

This on-call independent contractor opportunity offers flexibility while allowing you to make a meaningful impact on transportation safety across North America. You’ll work with experienced transportation professionals, deliver a professional Train-the-Trainer program, and help shape the next generation of driver instructors. You’ll enjoy variety in your work through travel to training locations across the Continental United States, combining classroom instruction with practical behind-the‑wheel coaching. You’ll have the autonomy to manage your travel and training assignments while representing Descartes in a highly visible role.

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

Contractors are expected to provide:

• 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 that we are hiring in:

• 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

Join Us

As we scale, we’re looking for new doers, collaborators and innovators to join Descartes in uniting the people and technology that move the world as the Global Leader in Logistics and Supply Chain Technology. We’re entrepreneurial, hardworking, geeky-in-a-good way problem solvers. Guided by our values, we nurture a TEAM focused culture that invests in people and creates opportunities for advancement across a broad spectrum of career paths. We prioritize work-life balance and foster an environment with the space to take ownership, to be heard, and to carve a path for your individual accomplishments to help drive our success. At Descartes, everyone has a voice and the best idea wins, regardless of who makes it. We offer competitive compensation, great benefits, remote and flexible work hours, and the opportunity to join a company on an awesome mission with a great existing team and trajectory.

Descartes also has a deep sense of environmental responsibility. Learn more about how we helped our customers save over 552,000 metric tons of CO2 in 2020 by reducing fuel and paper consumption: https://www.descartes.com/who-we-are/social-responsibility-sustainability/environmental-impact. Join a team that’s committed to working with customers to conserve resources and enhance sustainability.

We are an Equal Employment employer. We do not discriminate in hiring on the basis of sex, gender identity, sexual orientation, race, color, religious creed, national origin, physical or mental disability, protected status, or any other characteristic protected by federal, provincial, or local law. For more information about our commitment to equal employment opportunity, please review our Code of Business Conduct and Ethics at Descartes.com. Descartes is committed to working with and providing reasonable accommodations to job applicants with disabilities. Applicants in North America with a disability who require a reasonable accommodation for any part of the application or hiring process can email us at [e-mail]. Provide your name and contact information along with the accommodation needed to assist you with the application process. Your request will be responded to as soon as possible. Reasonable accommodations will be determined on a case‑based basis.