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Owner Driver Jobs in Massachusetts (NOW HIRING)

Roadie

Box Truck Owner

Somerville, MA · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

Roadie

Box Truck Owner

Chelsea, MA

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

Roadie

Box Truck Owner

Jamaica Plain, MA · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

Roadie

Box Truck Owner

Sharon, MA · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

Roadie

Box Truck Owner

South Boston, MA

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

Roadie

Box Truck Owner

Malden, MA

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

Roadie

Box Truck Owner

Brookline, MA

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world ... Drivers can earn up to $200 delivering RoadieXD™ Routed Gigs using the Roadie App! Roadie is a ...

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Showing results 1-20

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 Sep 1, 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 1% As Needed, 66% Full Time, 30% Part Time, and 3% Contract. Highlights an 97% Physical, and 3% Remote job distribution, with an average salary of $249,633 per year, or $120 per hour.

MA Regional Drivers • New Pay Scale • Weekend Home Time • 5X Best Fleets!

Springfield, MA • On-site

Leonard's Express Inc
Trucking • 501 - 1,000 employees

7.6

Company rating: 7.6 out of 10

Based on 5 frontline employees who took The Breakroom Quiz

Good employer

Learn more about Leonard's Express Incexternal

$1.2K - $1.6K/wk

Per diem

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 6 days ago

Job description

Description:

Regional Drivers • New Pay Scale • Weekend Home Time Options • 5X Best Fleets Winner!

Leonard’s Express is built for longevity, celebrating our 25th anniversary. Built on family values. Built on respect.

If you’re not getting the miles, the money, the maintenance, or the respect you deserve, it’s time to move to a carrier that's invested in your success — not just your truck number.

We’re family-owned, driver-focused, and proud to be a 5X Best Fleets to Drive For carrier AND a Top Company for Women to Work in Transportation for 3 years running.

Our motto? Do the Right Thing. Always.

Pay (Top CPM Regional CDL Pay):

  • 0–250 Mile Loads: $0.80 CPM
  • 251–500 Mile Loads: $0.70 CPM
  • 501+ Mile Loads: $0.60 CPM

PLUS $25 for Every Live Load or Unload

Home Time:

  • Northeast Regional Drivers: Home every weekend
  • Atlantic Coastal Regional Drivers: 75% of weekly home time is on weekends

New Top Pay • Top-of-the-Line Equipment • Latest Technology

Benefits & Features:

  • Per Diem Pay Optional
  • Health, dental, vision, and life insurance
  • Paid Time Off (PTO) & holiday pay
  • 401K with company match
  • Weekly Direct Deposit
  • No Touch Freight
  • ISAAC, ELOG, EZPASS, PREPASS
  • Late Model Equipment
  • Paid Orientation
  • Full-Service Terminals and 24/7 Dispatch & Road Service
  • Pet and rider policy
  • Satellite radio in all trucks

It’s not just a seat. It’s a home.
It’s not just a load. It’s a future.
It’s time to love trucking again.

Requirements:

Requirements (Class A CDL):

  • 6 months OTR experience required
  • Must be 21 or older

APPLY NOW:
https://drive4leonards.com

Call: 585-869-3108

What Leonard's Express employees say

Workplace

Get the full story on Breakroom