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Owner Operator Jobs in Windsor, CT (NOW HIRING)

Clark Transfer Inc

CDL A Owner Operator

Middletown, CT

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Hartford, CT

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Wallingford, CT

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Enfield, CT

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Bristol, CT

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Roadie

Box Truck Owner Operator

Cheshire, CT · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world of high-paying delivery tailored just for your vehicle. Your box truck or cargo van is more than just ...

Posted today

Roadie

Box Truck Owner Operator

Wallingford, CT · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world of high-paying delivery tailored just for your vehicle. Your box truck or cargo van is more than just ...

Posted today

Roadie

Box Truck Owner Operator

Wallingford, CT · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world of high-paying delivery tailored just for your vehicle. Your box truck or cargo van is more than just ...

Posted today

Roadie

Box Truck Owner Operator

Cheshire, CT · On-site

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world of high-paying delivery tailored just for your vehicle. Your box truck or cargo van is more than just ...

Posted today

Roadie

Box Truck Owner Operator

Wallingford, CT

$117 - $135/day

Are you an owner of a cargo van, or box truck looking to maximize your earnings? Discover a world of high-paying delivery tailored just for your vehicle. Your box truck or cargo van is more than just ...

Posted today

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Showing results 1-20

All JobsOwner Operator JobsOwner Operator Jobs in Windsor, CT

Owner Operator information

See Windsor, CT salary details

$641

$4.4K

$7.6K

How much do owner operator jobs pay per week?

As of Aug 21, 2026, the average weekly pay for owner operator in Windsor, CT is $4,375.96, according to ZipRecruiter salary data. Most workers in this role earn between $2,392.31 and $6,509.62 per week, depending on experience, location, and employer.

What is an owner operator?

Owner operators are independent truck drivers or small business owners who own and operate their own commercial vehicles. They either lease their services to larger freight carriers or contract directly with clients to transport goods. Unlike company drivers, owner operators are responsible for managing their own business expenses, such as fuel, maintenance, insurance, and taxes. This role offers more autonomy and the potential for higher earnings, but it also comes with greater financial risk and responsibility.

What does an owner operator do?

The term Owner-Operator refers to a trucking professional who owns their truck and drives it as an independent contractor. Many companies hire independent operators to haul goods for them. Using contractors allows construction companies to keep pace with the rise and fall of demand for their products without the overhead cost of maintaining a fleet of vehicles that may be insufficient in one season and excessive in another. Owner-Operators need to hold a Commercial Driver's License (CDL) in the class that allows them to drive their vehicle and have sufficient training in operating and maintaining the machine. They can choose their own schedule and pick which jobs to take.

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

To thrive as an Owner Operator, you need a valid commercial driver's license (CDL), strong knowledge of transportation regulations, and experience in truck driving and logistics. Familiarity with fleet management software, GPS navigation systems, and compliance tools like electronic logging devices (ELDs) is essential. Excellent time management, business acumen, and customer service skills help set top performers apart in this role. These skills and qualities are crucial for ensuring safe, efficient operations and building a successful, profitable transportation business.

What are common challenges owner operators face when managing their own trucking business?

Owner Operators often encounter challenges such as maintaining cash flow, managing fluctuating fuel costs, and ensuring their vehicles are properly maintained to avoid unexpected downtime. Balancing administrative tasks—like scheduling, invoicing, and compliance—with time on the road can also be demanding. Building relationships with reliable clients or brokers and navigating complex regulations are crucial for long-term success. Staying organized and proactive in handling these responsibilities helps Owner Operators thrive in a competitive industry.

What is the difference between Owner Operator vs Truck Driver?

AspectOwner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, basic driving license
Work EnvironmentOwn truck, self-managed scheduleCompany-owned trucks, set schedules
EmployerSelf-employed or independent contractorEmployers or carriers
Work FlexibilityHigh, controls own routes and hoursLimited, dictated by employer

Owner Operators own and operate their trucks, managing their own schedules and business. Truck Drivers typically work for a company, following set routes and schedules. The main difference lies in independence and business ownership, with Owner Operators having more control but also more responsibilities.

More about Owner Operator jobs

What are the most commonly searched types of Owner Operator jobs in Windsor, CT?

The most popular types of Owner Operator jobs in Windsor, CT are:

What are popular job titles related to Owner Operator jobs in Windsor, CT?

For Owner Operator jobs in Windsor, CT, the most frequently searched job titles are:

What job categories do people searching Owner Operator jobs in Windsor, CT look for?

The top searched job categories for Owner Operator jobs in Windsor, CT are:

What cities near Windsor, CT are hiring for Owner Operator jobs?

Cities near Windsor, CT with the most Owner Operator job openings:

Owner Operator jobs near you
Infographic showing various Owner Operator job openings in Windsor, CT as of August 2026, with employment types broken down into 43% Full Time, 51% Part Time, 4% Temporary, 1% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $227,550 per year, or $109.4 per hour.

Flatbed Owner Operator

JRC Transportation Inc.

Thomaston, CT • On-site

$150K - $250K/yr

Contractor

Posted 9 days ago

Job description

JRC Transportation, Inc. is seeking experienced Flatbed Owner Operators to lease on with our fleet. As a 40+ year asset based flatbed carrier specializing in building materials and industrial freight, we offer consistent freight, competitive rates, and a supportive dispatch team. This is an independent contractor opportunity for drivers who own their own tractor and want reliable flatbed lanes with a company known for safe, dependable, on time delivery.

Responsibilities
  • Safely operate a flatbed tractor trailer to transport building materials and industrial freight
  • Properly secure, tarp, and protect cargo using dunnage, chains, and binders per DOT and company standards
  • Complete pre and post trip inspections and maintain accurate logbooks or ELD records
  • Communicate proactively with dispatch on load status, delays, and delivery updates
  • Maintain required permits, licenses, and documentation in JRC binder
  • Comply with all DOT regulations and maintain a clean driving record
  • For oversize and heavy haul loads: properly display oversize signage, flagging, and safety triangles, and coordinate with pilot or escort vehicles when required
Requirements
  • 3+ years verifiable OTR experience (must be 24+ years old), OR 24 to 36 months verifiable OTR experience (must be 23+ years old)
  • Clean driving record: no more than 1 at fault accident and limited moving violations in the past 3 years
  • No DUI/DWI, reckless driving, or license suspension/revocation convictions
  • Drivers over 65 must pass an annual DOT physical and eye exam
  • Military drivers with Class A experience in the last 5 years may qualify with less OTR time
  • For oversize/heavy haul loads: 2+ years experience for loads under 100,000 lbs/14', or 4+ years for loads over that, with a clean recent record
  • Must have or be able to obtain required flatbed and safety equipment (tarps, chains, PPE, ELD, etc.)
Benefits
Flexible Schedule###Mon-Fri Schedule###Career Growth Opportunities###