W2 CDL Driver Jobs in Massachusetts September 2026

Trancasa USA Inc

OTR CDL-A Truck Driver | Up to 60 CPM

Hiring in Massachusetts and 46 other locations
Weekly
$0.60 Per mile

Health, dental, and Vision benefits. Free life insurance. Weekly performance bonus.
Trucks in great conditions. Up to 60 cent per mile. CDL Driver. Full-time Job Position.
Trancasa USA, Inc. provides equal employment opportunities to all employees and applicants.

Soldwedel And Horn Enterprises Inc

OTR Solo Reefer Truck Driver | 73-80 CPM

Hiring in Massachusetts and 46 other locations
Weekly
$0.73 - 0.80 Per mile

No Driver Load / Unload. No slip seating. Company Driver (W2, Solo). Refrigerated.
Get 2 days of home time for every 10 days worked. 7 - 21 expected days out.
Benefits: Medical, Life and Disability. Paid vacation. Accommodation is covered.

Estes Express Lines

Regional CDL-A Driver | Fully Endorsed | 74-80 CPM

Hiring in Massachusetts and 4 other locations
Flexible
$0.74 - 0.80 Per mile

Starting mileage rate of 74 - 80 CPM. Schedule - Night Shift. Two weeks paid time off plus holidays.
Short- and long-term disability plans; life and AD&D insurance. Employee disaster relief fund.
Financial wellness program. Employee discount benefit program. Safety and referral bonus eligibility.

Leggett & Platt Inc

OTR CDL-A Truck Drivers | $75K - $90K Per Year

Hiring in Massachusetts and 46 other locations
2 weeks out
$75,000 - 90,000 Per year

Quarterly Safety & Performance Bonuses Start Day 1! Passenger & Pet Friendly. 9 Paid Holidays
Tenure Pay Starting at 6 Months of Service. Medical, Dental, Vision, and Life Insurance.
80% Company Freight. Non-Hazmat Freight. Full Fleet Electronic Logs. Limited Touch Freight.

Ashley Distribution Services LTD

CDL-A OTR Pacific Northwest Truck Driver | 53 CPM

Hiring in Massachusetts and 46 other locations
Weekly
$0.53 Per mile

Generous benefits package. Modern fleet of well-maintained 2015-2023 model year trucks.
Steady general freight. 70% pre-loaded pickups and 30% drop deliveries.
Pre-planned OTR routes in the Western states with the chance to see all 48 states.

Witte Brothers Exchange Inc

CDL-A OTR Truck Driver | Up to 65 CPM

Hiring in Massachusetts and 46 other locations
Weekly
$0.50 - 0.65 Per mile

State-of-the-art Freightliner and Peterbilt trucks. Health, dental, and vision insurance.
401(k) with company match. Supplemental pay: detention, stop pay, layover. Steady freight.
Advanced tech: ELDs, GPS/Co-Pilot, driver app. Driver appreciation program & monthly bonuses.

Prima Express Inc.

OTR CDL-A Experienced Truck Driver | Up to 60CPM

Hiring in Massachusetts and 46 other locations
2 weeks out, 3 weeks out
$0.56 - 0.60 Per mile

Up to 0.60 CPM start (Depending On Experience). Average 2800-3200 Miles Per Week. Earn from $80,000.00 up to $100,000 per year.
All practical miles paid loaded and empty. Weekly Pay via Direct Deposit. 80% Drop and Hook and100% No-Touch Freight.
Full Benefits Including: Medical, Dental, Life, Vision, 401k Retirement Plan, Pet and Rider Policy. W2 Company Paid Employee NO 1099.

Countryside Auto Transport Inc

OTR CDL-A Car Hauler | Up to $100,000+/year

Hiring in Massachusetts and 46 other locations
Flexible
$75,000 - 100,000 Per year

Up to $100,000+/year (includes CPM, per diem, pay per car). +0.10 for east coast miles. +$20.00 per car loaded.
Routes: NO Northwest and New York City. Late Model Equipment. All automatics. Full Benefit Package.
Insurance: Health, Dental, Life, Vision, Short-term disability. 401K, Employer match. Vacation Pay.

Magari Enterprises, Inc.

CDL A Lease To Purchase Owner Operator

Hiring in Massachusetts and 45 other locations
Flexible
$6,000 - 9,000 Per week

0$ Payment Down and NO credit check history.
NO BALLOON PAYMENT. Walk away lease.
Fuel card. Fuel discount. Referral program.

A&J Transportation

Class A CDL Truck Drivers | $2,300/week

Hiring in Massachusetts and 46 other locations
Weekly
$1,500 - 2,300 Per week

30% of pay with experience, move to 31% after 1 year.
Pay: $1,500.00 - $2,300.00 per week.
Paid vacations. Daily orientation pay. Weekly cash advances.

Longistics

OTR Team Drivers CDL A

Hiring in Massachusetts and 46 other locations
Few times per week
$0.80 Per mile

Average $4,000 Per Week, Split Between Drivers.
Free insurance, dedicated fleet, flexible hometime options.
Quarterly Bonus & Referral programs.

Artur Express, Inc./TTS Logistics

OTR CDL-A Driver | Dry Van and Reefer

Hiring in Massachusetts and 46 other locations
Flexible
$0.53 - 0.67 Per mile

Miles and money - Our OTR solo drivers average 2,800 - 3,000 miles per week.
Staff available 24/7 to keep you moving.
Pay based on performance – we can help you grow and succeed.

Crete Carrier Corporation

CDL A Dry Van Company Driver | OTR

Hiring in Massachusetts and 46 other locations
Weekly
$0.60 - 0.63 Per mile

OTR Starting Pay: 60 to 63 CPM, depending on experience.
Industry Leading Benefits. Safe Driver Productivity Bonus.
Annual profit sharing: Contributed $13 million towards employee profit sharing in 2023!

System Transport

OTR CDL A Flatbed Driver | 55-60 CPM

Hiring in Massachusetts and 46 other locations
Weekly
$0.55 - 0.60 Per mile

Experienced Flatbed CDL-A drivers. OTR route. Medical, dental, vision & life insurance.
Earn $.55 to $.60 per mile or $900 - $1,600 per week (depending on experience).
Full pay package also includes other accessorial compensation.

America's Catch Inc.

CDL A OTR Truck Driver Position With Benefits

Hiring in Massachusetts and 46 other locations
Weekly
$552 - 2,350 Per week

Annual pay can range from $70,000 to $100,000. Record/Experience Considered.
Company Paid Health Insurance, Dental, Vision, and Disability Insurance available, Vacation Pay
Well maintained dedicated equipment, average age of Tractor fleet less than 3 years

W2 CDL driver jobs in Massachusetts