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Independent Contractor Flight Instructor Jobs in Baltimore, MD

TEAM FX

Group Fitness Instructor

Baltimore, MD · On-site

Independent Contractor FX Studios is committed to providing exceptional customer service to each and every guest! An FX Studios Instructor is responsible for delivering a safe, effective, and ...

TEAM FX

Group Fitness Instructor

Baltimore, MD

Description Independent Contractor FX Studios is committed to providing exceptional customer service to each and every guest! An FX Studios Instructor is responsible for delivering a safe, effective ...

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All JobsIndependent Contractor Flight Instructor JobsIndependent Contractor Flight Instructor Jobs in Baltimore, MD

Independent Contractor Flight Instructor information

See Baltimore, MD salary details

$24.8K

$94K

$144.6K

How much do independent contractor flight instructor jobs pay per year?

As of Jul 26, 2026, the average yearly pay for independent contractor flight instructor in Baltimore, MD is $94,018.00, according to ZipRecruiter salary data. Most workers in this role earn between $68,600.00 and $111,300.00 per year, depending on experience, location, and employer.

What are some common challenges faced by Independent Contractor Flight Instructors and how can they be managed?

Independent Contractor Flight Instructors often face challenges such as fluctuating student demand, variable scheduling, and managing their own administrative tasks like billing and record-keeping. Unlike salaried instructors, they must proactively market their services and maintain relationships with local flight schools or fixed-base operators. To manage these challenges, successful instructors often develop strong organizational skills, use scheduling and billing software, and build a network within the aviation community to ensure a steady flow of students. Establishing clear communication with clients and maintaining flexibility in scheduling also contribute to long-term success.

What is an Independent Contractor Flight Instructor?

An Independent Contractor Flight Instructor is a certified pilot who provides flight training services on a freelance or contract basis, rather than being employed directly by a flight school or aviation company. They typically work for themselves, setting their own schedules, rates, and terms of service. Independent contractors may instruct at various locations, use their own or rented aircraft, and are responsible for their own taxes and insurance. This role offers flexibility and autonomy but also requires strong business management skills and compliance with aviation regulations.

What are the key skills and qualifications needed to thrive as an Independent Contractor Flight Instructor, and why are they important?

To thrive as an Independent Contractor Flight Instructor, you need a valid Certified Flight Instructor (CFI) certificate, strong piloting skills, and a thorough understanding of aviation regulations and safety protocols. Familiarity with flight training devices, aviation weather systems, and logbook management software is typically required. Excellent communication, patience, and adaptability help instructors tailor lessons to individual student needs and foster a safe learning environment. These skills ensure effective student instruction, regulatory compliance, and a reputation for professionalism in the aviation industry.
What are the most commonly searched types of Flight Instructor jobs in Baltimore, MD? The most popular types of Flight Instructor jobs in Baltimore, MD are:
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What job categories do people searching Independent Contractor Flight Instructor jobs in Baltimore, MD look for? The top searched job categories for Independent Contractor Flight Instructor jobs in Baltimore, MD are:
What cities near Baltimore, MD are hiring for Independent Contractor Flight Instructor jobs? Cities near Baltimore, MD with the most Independent Contractor Flight Instructor job openings:
Independent Contractor Flight Instructor jobs near you
Infographic showing various Independent Contractor Flight Instructor job openings in Baltimore, MD as of July 2026, with employment types broken down into 33% Full Time, 25% Part Time, and 42% Contract. Highlights an 92% In-person, and 8% Remote job distribution, with an average salary of $94,018 per year, or $45.2 per hour.
On-Call Independent Contractor- Trainer

On-Call Independent Contractor- Trainer

The Descartes Systems Group, Inc.

Silver Spring, MD

Other

Posted 11 days ago

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.


We're growing fast and invite you to join our amazing team. 
 

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

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:
o    Professional driving techniques
o    Professional parking and backing techniques
o    Defensive driving principles
o    DOT regulations
o    CSA compliance
o    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

#LI-Remote

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.

If you feel you have 70% of the qualifications we are looking for, and Descartes sounds like the team and the mission you want to be part of, apply now. We can't promise it will be a fit, but we do promise to consider your experience.

Through COVID-19, we implemented a virtual hiring process and continue to interview and onboard candidates by video using Microsoft TEAMS. We record interviews and use them strictly for quality assurance, training and general record keeping purposes. Should you have any questions about this process, please connect with our hiring team in advance of scheduled interviews. We value the safety of each member of our community because we know we're all in this together. 

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 hrna@descartes.com. 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-by-case basis.

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