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Owner Driver Jobs in Massachusetts (NOW HIRING)

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CDL-A Owner Operator Driver

Boston, MA · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Haverhill, MA · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Feeding Hills, MA · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Mattapoisett, MA · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Provincetown, MA · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Middleborough, MA · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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All JobsOwner Driver JobsOwner Driver Jobs in Massachusetts

Owner Driver information

See Massachusetts salary details

$703

$4.8K

$8.4K

How much do owner driver jobs pay per week?

As of Aug 22, 2026, the average weekly pay for owner driver in Massachusetts is $4,800.63, according to ZipRecruiter salary data. Most workers in this role earn between $2,625.00 and $7,140.38 per week, depending on experience, location, and employer.

What is an owner driver?

Owner drivers are individuals who own and operate their own vehicles to provide transportation or delivery services. Instead of working for a company as an employee, they contract their services independently or with companies that require delivery or transport, such as courier firms or logistics providers. Owner drivers are responsible for the maintenance, insurance, and running costs of their vehicles. They often enjoy flexible working hours and the ability to be their own boss, but they also bear the risks and responsibilities of self-employment.

What are the key skills and qualifications needed to thrive as an owner driver?

To thrive as an Owner Driver, you need a valid commercial driver's license, strong driving skills, and a good understanding of vehicle maintenance and logistics operations. Familiarity with GPS navigation systems, electronic logging devices (ELDs), and fleet management software is typically required. Excellent time management, customer service, and problem-solving abilities help owner drivers deliver goods efficiently and build client relationships. These skills are crucial for ensuring safe, timely deliveries, maintaining a reliable business, and achieving customer satisfaction.

What are some of the common challenges faced by owner drivers, and how can they be managed effectively?

Owner Drivers often face challenges such as fluctuating fuel costs, vehicle maintenance expenses, and finding consistent work. Managing these challenges involves careful budgeting, regular vehicle upkeep to avoid unexpected breakdowns, and building strong relationships with clients or freight brokers for steady contracts. Many Owner Drivers also use technology platforms to find jobs and track deliveries efficiently, helping to maximize their earning potential and reduce downtime.

What is the difference between Owner Driver vs Delivery Driver?

AspectOwner DriverDelivery Driver
CredentialsDriver's license, vehicle registrationDriver's license, sometimes specific delivery certifications
Work EnvironmentOwn vehicle, flexible schedule, independentCompany vehicle, structured routes, often employed
Employer/Industry UsageSelf-employed or small business owner in transportEmployed by delivery companies or logistics providers

Owner Drivers typically own their vehicle and operate independently, managing their own schedules and clients. Delivery Drivers are usually employed by companies, using company vehicles to complete assigned routes. Both roles require a valid driver's license, but Owner Drivers often handle their own vehicle maintenance and business administration, while Delivery Drivers focus on timely deliveries within a structured environment.

How to get work as an owner driver?

To get work as an owner driver, you should obtain the necessary vehicle licenses and insurance, register your vehicle with relevant authorities, and build relationships with logistics companies or clients. Having good driving skills, a clean driving record, and understanding scheduling and route planning can also improve your chances of securing work.

What are popular job titles related to Owner Driver jobs in Massachusetts?

For Owner Driver jobs in Massachusetts, the most frequently searched job titles are:

What job categories do people searching Owner Driver jobs in Massachusetts look for?

The top searched job categories for Owner Driver jobs in Massachusetts are:

Owner Driver jobs near you
Infographic showing various Owner Driver job openings in Massachusetts as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $249,633 per year, or $120 per hour.

CDL-A Company Driver - 2yrs EXP Required - Local - Highway Driver Leasing

Highway Driver Leasing

Milton, MA

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 21 days ago

Job description

Hiring CDL A Drivers | Hourly Pay | Home DAILY | Great Benefits.

Founded in 1984, Highway Driver Leasing has been New England’s trusted CDL driver partner. Our expert CDL drivers have been driving at companies across New England for over 40 years. As a family-owned business, we are committed to delivering strong relationships with both our drivers and our clients. Our mission is simple: to provide companies with reliable, highly qualified CDL drivers while offering our drivers safe and rewarding career opportunities.

GREAT REASONS TO JOIN OUR TEAM!

  • Hourly pay 29$ an Hr with Tax Free OT (Time and Half), 8-hour minimum pay per day
  • Home Daily - Full time and Part time available
  • Palletized loads, no hand unloading
  • Paid time off, health insurance
  • No forced dispatch - work as many hours as you want
  • Stable work
  • Always treated with dignity and respect
  • Safe equipment
  • Very low turnover
  • Always-expanding driver fleet
  • No automatic restrictions

Job Types: Full-time, Part-time

Benefits:

  • 401K
  • Dental insurance
  • Disability insurance
  • Health insurance
  • Life insurance
  • Paid sick time
  • Paid time off
  • Referral program
  • Vision insurance

QUALIFICATIONS:

  • A valid class A license
  • A minimum of 2 years of commercial driving experience
  • A clean driving record
  • Have a current DOT medical card
  • Commitment to safe driving practices

Apply