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Owner Operators Jobs in Massachusetts (NOW HIRING)

RidenRoll

Limo Owner-Operators

Boston, MA · On-site

Your safety is our top priority! Company Overview: RIDENROLL (www.RidenRoll.com) is a California-based, for-profit technology platform that connects users with ride-hauling drivers and delivery ...

STG Logistics

Owner Operator

Worcester, MA · On-site

Worcester Owner-Operators Needed for Intermodal & Drayage Freight Text APPLY to (860) 300-2110 to get your quick app started! STG Drayage is growing its intermodal and drayage network and looking to ...

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Owner Operators information

See Massachusetts salary details

$703

$4.8K

$8.4K

How much do owner operators jobs pay per week?

As of Aug 30, 2026, the average weekly pay for owner operators 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 operator?

An Owner Operator is a self-employed truck driver who owns and operates their own commercial vehicle. They either haul freight for a company under a contract or run their own independent trucking business. Responsibilities include managing expenses, securing contracts, maintaining their truck, and complying with industry regulations. Being an Owner Operator provides more control over routes and schedules but also comes with financial risks and business management responsibilities.

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

To thrive as an Owner Operator, you need strong business management skills, a commercial driver's license (CDL), and a thorough understanding of transportation regulations and logistics. Familiarity with electronic logging devices (ELDs), freight brokerage platforms, and route planning software is often necessary. Excellent time management, self-motivation, and communication skills set standout candidates apart in this competitive field. These skills and qualities are vital to efficiently manage your own business, ensure regulatory compliance, and maintain reliable client relationships.

What are some common challenges faced by owner operators and how can they be managed?

Owner Operators often encounter challenges such as fluctuating fuel costs, finding consistent loads, maintaining their vehicles, and keeping up with regulatory requirements. Staying organized with digital tools for load planning and maintenance scheduling can help streamline operations. Building strong relationships with freight brokers and direct shippers may increase access to steady work, while careful budgeting can assist in managing overhead expenses. Additionally, keeping up-to-date with industry regulations can ensure your business remains compliant and operates smoothly. Addressing these challenges proactively helps promote a successful and sustainable operation.

How do owner operators find jobs?

Owner operators find jobs through load boards, freight brokers, and direct relationships with shippers or carriers. They often use online platforms, industry networks, and maintain good communication to secure consistent work, while also managing necessary licenses and insurance requirements.

How much do most owner operators make?

Most owner operators earn between $100,000 and $200,000 annually, depending on factors such as experience, routes, and load types. Earnings can vary widely based on fuel costs, maintenance, and operational efficiency, with successful operators often managing their own schedules and equipment to maximize profit.

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

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

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

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

What cities in Massachusetts are hiring for Owner Operators jobs?

Cities in Massachusetts with the most Owner Operators job openings:

Owner Operators jobs near you
Infographic showing various Owner Operators job openings in Massachusetts as of August 2026, with employment types broken down into 84% Full Time, 11% Part Time, 1% Temporary, 3% Contract, and 1% Nights. Highlights an 92% Physical, 3% Hybrid, and 5% Remote job distribution, with an average salary of $249,633 per year, or $120 per hour.

Limo Owner-Operators

RidenRoll

Boston, MA • On-site

Full-time

Re-posted 13 days ago

Job description

Your safety is our top priority!
Company Overview:
RIDENROLL (www.RidenRoll.com) is a California-based, for-profit technology platform that connects users with ride-hauling drivers and delivery services at competitive prices. We are dedicated to delivering top-notch services, fostering a competitive market, and ensuring a low-risk environment for all. We also provide SaaS and Employer Support Services.
Schedules & Benefits:
Enjoy a flexible schedule, drive whenever you choose, be your boss, and set your hours. With RidenRoll's SaaS Employer Support Services, you can scale your business from a single-person operation to a large enterprise.
Qualifications:
  • 21+ years of age or meet the minimum age to drive in your city where driving.
  • Valid US driver's license.
  • You have an iPhone or Android smartphone.
  • Proof of residency in your city, state, or province.
  • Proof of vehicle insurance
  • Proof of vehicle inspection performed by the California Bureau of Automotive Repair and uploaded to the www.ridenroll.com driver app when applying.
  • A driver profile's latest photo.
  • 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 We Offer:
  • Access to state-of-the-art technology and tools.
  • Opportunities for growth and development within a dynamic team.
  • Supportive and collaborative work environment.

Download the RidenRoll App in the App Store and/or Google Play

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