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Owner Operator Contractor Jobs in Boston, MA (NOW HIRING)

ALFA FREIGHT INC

Box Truck Owner Operator OTR

Lowell, MA · On-site

$5.5K - $8.0K/wk

NON CDL Box Truck Owner-Operator (OTR) - $5,500 - $8,000 Weekly We are seeking committed contractors to run one of the OTR routes available What We Offer: * Weekly gross earnings: $5,500 - $8,000 ...

RidenRoll

Limo Owner-Operators

Boston, MA · On-site

W-9 form for 1099 contractors. * Comfortable using GPS navigation apps. Vehicle Requirements: * Less than 10 years old. * 4 doors * 5-8 seats, including the drivers. * Local state license plate. What ...

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All JobsOwner Operator Contractor JobsOwner Operator Contractor Jobs in Boston, MA

Owner Operator Contractor information

See Boston, MA salary details

$699

$4.8K

$8.3K

How much do owner operator contractor jobs pay per week?

As of Aug 20, 2026, the average weekly pay for owner operator contractor in Boston, MA is $4,775.48, according to ZipRecruiter salary data. Most workers in this role earn between $2,611.54 and $7,103.85 per week, depending on experience, location, and employer.

What is an owner operator contractor?

Owner Operator Contractors are self-employed individuals or businesses who own and operate their own vehicles or equipment to provide transportation or delivery services. They typically contract with larger companies or clients to haul goods, manage logistics, or perform specialized tasks, often in the trucking or freight industry. As independent contractors, they are responsible for maintaining their equipment, managing expenses, and complying with regulations. This role offers greater flexibility and profit potential but also comes with higher risks and responsibilities compared to company-employed drivers.

What are some common challenges owner operator contractors face when managing their own business?

Owner Operator Contractors often face challenges related to balancing driving duties with the administrative responsibilities of running a business. Tasks such as handling contracts, maintaining equipment, managing finances, and securing consistent loads can require significant time and attention. Additionally, they are responsible for compliance with safety regulations and industry standards, which can be complex and ever-changing. Many find that building relationships with brokers and shippers is essential for steady work, and effective time management is key to maintaining profitability.

What are the key skills and qualifications needed to thrive as an owner operator contractor, and why are they important?

To thrive as an Owner Operator Contractor, you need a valid commercial driver's license (CDL), a clean driving record, and business management knowledge. Familiarity with electronic logging devices (ELDs), GPS systems, and compliance with Department of Transportation (DOT) regulations is essential. Strong organizational skills, self-motivation, and effective communication set top performers apart in managing routes and client relationships. These skills ensure safe, efficient operations and sustainable business growth in the competitive logistics industry.

What is the difference between Owner Operator Contractor vs Truck Driver?

AspectOwner Operator ContractorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCommercial Driver's License (CDL)
Work EnvironmentOwn truck, independent, flexible scheduleCompany-owned trucks, fixed routes, employer-managed
Employer/Industry UsageSelf-employed or contracted with carriersEmployed by trucking companies
Search/Comparison IntentHigh overlap in responsibilities and credentialsDifferent in independence and employment status

In summary, Owner Operator Contractors own and operate their trucks independently, often contracting with carriers, while Truck Drivers are typically employed by companies and operate company-owned vehicles. Both roles require a CDL, but their work setup and employment status differ significantly.

What are popular job titles related to Owner Operator Contractor jobs in Boston, MA?

For Owner Operator Contractor jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Owner Operator Contractor jobs in Boston, MA look for?

The top searched job categories for Owner Operator Contractor jobs in Boston, MA are:

Owner Operator Contractor jobs near you
Infographic showing various Owner Operator Contractor job openings in Boston, MA as of August 2026, with employment types broken down into 46% Full Time, 50% Part Time, 3% Contract, and 1% Nights. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $248,325 per year, or $119.4 per hour.

Box Truck Owner Operator OTR

ALFA FREIGHT INC

Cambridge, MA • On-site

$5.5K - $8.0K/wk

Full-time

Re-posted 20 days ago

Job description

NON CDL Box Truck Owner-Operator (OTR) – $5,500 - $8,000 Weekly

We are seeking committed contractors to run one of the OTR routes available

What We Offer:

  • Weekly gross earnings: $5,500 – $8,000

  • 88% of gross goes to the driver, 12% service fee 

  • Onboarding in as little as 1 day
  • Fuel card program with a starting discount of $0.30/gallon
  • Referral bonus, Clean inspection bonus
  • General freight – mostly no-touch
  • Assistance in acquiring your own MC
  • Steady OTR deliveries across the continental U.S.

Support:

  • No forced dispatch

  • No factoring fees

  • OTR freight across 48 states

  • 2 weeks out

  • Fuel card program with discounts

  • Sign-on bonus available

  • Clean DOT inspection bonus

  • 24/7 ELD and safety support

Requirements:

  • 24’ or 26’ box truck (model year 2013 or newer)

  • At least 6 months of verifiable OTR experience

  • Regular driver's license

  • No more than 1 moving violation in the past 2 years

  • Familiarity with ELD systems

Call our team and start in a day: 872-259-1406
Apply now, and our team will contact you within 24 hours.