11 Massachusetts Fleets Where a New CDL Meets a New Chapter

The Bay State employed around 32,890 heavy-truck drivers in 2023.

State-of-the-road facts

  • The Bay State employed around 32,890 heavy-truck drivers in 2023.
  • Massachusetts’ expanded CORI “Ban-the-Box” law keeps conviction questions off most first-round applications.

Eleven local fleets giving rookies and returning citizens a fair shot

1. Sysco 📍 Boston

Paid trainee program; employees confirm felony hires on a case-by-case basis. See open jobs here.

2. US Foods 📍 Boston

Similar to Sysco; older convictions frequently approved. See open jobs here.

3. R+L Carriers 📍 Wilmington

Has a track record of being a second chance employer. See open jobs here.

4. Ward Trucking 📍 Westfield

Has a track record of being a second chance employer. See open jobs here.

5. Werner Enterprises 📍 Worcester

One of the largest trucking companies in the USA and Mexico with a record of bring a second chance employer. See open jobs here.

6. Knight Transportation 📍 Plainville

Many regional routes avaialble. See open jobs here.

7. Swift Transportation 📍 Multiple Locations in MA

A top national carrier that's a regular second chance employer. See open jobs here.

8. Republic Services 📍 Statewide

No-experience bonus: CDL Driver-Trainee program pays you while you earn the license—perfect for brand-new grads. See open jobs here.

9. Wind River Environmental 📍 Marlborough

Septic & grease-traps local routes and promotes from within. See open jobs here.

10. Boston Concrete 📍 Boston & Lowell

Small ready-mix outfit that hires on attitude and MVR, not years behind the wheel—open driver postings pop up regularly. See open jobs here.

11. Bay State Sewage & Disposal📍 Lakeville

Family-owned pump-truck fleet. See open jobs here.

Hottest Bay-State CDL-A roles today

  • Food-Service Shuttle & Route – early start, home daily, union bennies.

  • Night LTL Line-Haul – doubles pay premium + predictable out-and-back runs.

  • Boston Local Grocery & Beverage – Stop & Shop, Shaw’s, etc.

  • Intermodal Port of Boston – hourly chassis pay, minimal deadhead.

  • Bulk Septic / Environmental Services – Wind River & Bay State need CDL pump-truck drivers year-round.

Your two-day action plan

  1. Blast out 10 apps (start with the table above).

  2. Email your Emerge Career coach the minute they’re sent—your coach will share our Massachusetts partner spreadsheet and line up warm recruiter intros at Sysco, Republic Services, and Wind River.

  3. Keep practicing backing & alley-dock while you wait for calls—confidence shows in every road test.

Fast fact: Emerge Career learners who combine bulk applications with coach-led introductions average two solid offers in under 10 days.

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