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Transportation Contractor Jobs in Washington (NOW HIRING)

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Field Inspector 1099 Contractor

Waldorf, MD · On-site

A clean and reliable truck, van, or SUV that is capable of transporting a 32' ft ladder safely * An ... Strong support team for our 1099 independent contractor field inspectors * Hotel fees paid ...

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Field Inspector 1099 Contractor

Fairfax, VA · On-site

A clean and reliable truck, van, or SUV that is capable of transporting a 32' ft ladder safely * An ... Strong support team for our 1099 independent contractor field inspectors * Hotel fees paid ...

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All JobsTransportation Contractor JobsTransportation Contractor Jobs in Washington

Transportation Contractor information

See Washington salary details

$37.9K

$84.6K

$139.9K

How much do transportation contractor jobs pay per year?

As of Aug 20, 2026, the average yearly pay for transportation contractor in Washington is $84,606.00, according to ZipRecruiter salary data. Most workers in this role earn between $65,100.00 and $96,300.00 per year, depending on experience, location, and employer.

What is a transportation contractor?

Transportation contractors are independent businesses or individuals hired to provide transportation services, such as delivering goods, materials, or passengers, on behalf of another company or organization. They typically own or lease their own vehicles and are responsible for managing their schedules, routes, and compliance with safety regulations. Transportation contractors can work in various industries, including freight, logistics, courier services, and passenger transport. They often operate under a contractual agreement rather than as direct employees, giving them flexibility but also requiring them to handle their own taxes and insurance.

What are some common challenges transportation contractors face when coordinating deliveries across multiple locations?

Transportation Contractors often manage complex logistics, including route planning, scheduling, and adapting to unexpected delays such as traffic or weather. Balancing cost efficiency while meeting tight delivery deadlines can be challenging, especially when working with multiple clients or locations. Contractors must also stay compliant with transportation regulations and maintain clear communication with dispatchers, shippers, and receivers to ensure smooth operations. Proactively using route optimization software and maintaining flexibility in scheduling can help address these challenges.

What are the key skills and qualifications needed to thrive as a transportation contractor, and why are they important?

To thrive as a Transportation Contractor, you need a valid commercial driver's license (CDL), knowledge of logistics, and a good driving record. Familiarity with route planning software, GPS navigation systems, and compliance management tools is typically required. Strong time management, problem-solving abilities, and customer service skills help set top performers apart. These competencies ensure timely, safe deliveries and efficient operations, which are critical to client satisfaction and contract success.

What is the difference between Transportation Contractor vs Truck Driver?

AspectTransportation ContractorTruck Driver
CredentialsMay require commercial driver’s license (CDL), business licenses, and permitsTypically requires CDL and driving experience
Work EnvironmentSelf-employed or contracted work, managing multiple clients or companiesEmployed by a company or owner-operator, driving company or personal trucks
Employer/Industry UsageOperates independently or as part of a contracting business within logistics and freight industriesWorks for logistics companies, freight carriers, or as an owner-operator

Transportation Contractors often manage their own business operations, contracts, and schedules, while Truck Drivers typically work under an employer or as owner-operators focusing on driving tasks. Both roles require CDL licenses, but Transportation Contractors have additional responsibilities related to business management and client relations.

What job categories do people searching Transportation Contractor jobs in Washington look for?

The top searched job categories for Transportation Contractor jobs in Washington are:

Transportation Contractor jobs near you
Infographic showing various Transportation Contractor job openings in Washington as of August 2026, with employment types broken down into 1% As Needed, 59% Full Time, 31% Part Time, 2% Temporary, and 7% Contract. Highlights an 93% Physical, 1% Hybrid, and 6% Remote job distribution, with an average salary of $84,606 per year, or $40.7 per hour.

Class A CDL Owner Operator - 2yrs EXP Required - OTR - Diamond Transportation

Diamond Transportation

Washington, DC

Full-time

Re-posted 5 days ago

Job description

Diamond Transportation Signing OTR Owner Operators .

Signing: OTR Owner Operators (Accepting Independent Contractors W/ Trucks), MUST HAVE RGN, FLATBED OR STEPDECK EXPERIENCE with good knowledge of chaining, strapping and securement!


Company info:

Diamond Transportation System, Inc. has a rich history of pioneering the transportation of farm equipment and tractors starting in the 1940’s and expanded to the 100% Owner Operator Company with a Fortune 500 customer base that it is today. From humble beginnings to now serving the U.S. and Canada – transportation of Agricultural and Construction Equipment along with various types of Machinery is our specialty and our dedication to our customers and our contractors will carry us well into the next millennium.

Job Details:

  • Diamond has been in business for over 80 years.
  • Competitive pay
  • Weekly or Daily settlements – your choice
  • Personal ‘Guardian’ Fleet Manager to understand your individual needs
  • Non-forced Dispatch
  • Looking for Owner Operators with ‘open-deck’ experience to haul Flatbed, StepDeck, RGN (Removable Gooseneck) Trailers” ONLY!! 
  • Compensation packages include:
  • Percentage pay
  • Additional percent with your own trailer
  • Quarterly Safety Compensation
  • Referral compensation up to $2,500
  • No Trailer Rent
  • No Permit fees – we pay for the OD permits and you give us your routes
  • Sign on compensation (bonus)
  • Cargo and liability insurance at no additional cost
  • Available competitive insurance offerings for:
  • Physical Damage
  • Occupational Accident
  • NOTC/Bobtail
  • Passenger Authorization
  • Medical
  • License plate escrow (if plate needed)
  • Customer referral program
  • In-cab communications
  • ELD ready
  • Fuel card
  • Company RGN trailers
  • Fuel tax reporting
  • Fuel Discount Program
  • Tire Discount Program
  • We have Owner Operators just like YOU, leased to us for over 30 years.
  • Our family owned and operated company has only one concern, YOUR success as an Owner Operator.
  • We have the experience, the customer base and the freight to keep you making money.
  • Bottom Line…if YOU are successful, then we are successful.
  • It’s a partnership! We’re A 100% Owner Operator Company You won’t have any company trucks to compete with here!


Job Requirements:

  • MUST HAVE RGN, FLATBED & STEPDECK EXPERIENCE with good knowledge of chaining, strapping and securement!
  • If you can answer yes to these questions… Are at least 23 years old?
  • Does your background include six months of machinery / heavy haul / over-dimensional experience?
  • Do you have a good driving record?
  • Do you have a solid work history?
  • Can your truck pass a D.O.T. inspection

Apply