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Why Drive for Winston?

Interested? Enter your info below or call 631-924-1200!

  • Highest commissions paid.
  • No initial investments required.
  • Most jobs pay a 20% gratuity, you keep it all.
  • New accounts opening every day.
  • Help with TLC permits.
  • 24/7 dispatching and Call Center assists you.
  • Make more money with Demand-based pricing and Late night surcharges.
  • Flexible hours – part or full time, days or nights.
  • All area Airports, Piers, Wine Tours and Weddings.
  • Suffolk, Nassau, Queens, Brooklyn, Manhattan and Westchester, NJ and CT.
  • The most recognized name in Long Island’s transportation business.
  • A national online reservation system that puts passengers in your vehicle.
  • The newest fleet of Smoke-Free vehicles.
  • You are self-motivated, Independent, Highly professional.  You enjoy working with people and have a desire to exceed our customer expectations.

    If you have these qualities, you’ve got what it takes to be part of the Winston Transportation team.

    Our objective is to provide prompt, clean, courteous, safe and dependable ground transportation services to Fortune 500 companies, universities and individuals, 24 hours a day, 7 days a week.  We’ve been able to achieve this goal largely through the hard work and dedication of the talented people who work for us.


    • Minimum 21 years old.
    • Proficient in written and spoken English.
    • Motivated individuals with a strong knowledge of our service area.
    • Must have a desire to exceed our customers’ expectations.
    • Must be personable and customer service oriented.
    • Current NY driver’s license and a safe driving record.

    Airport Shuttle Drivers

    NY CDL, class C with P endorsement.

    Sedan/Limousine Drivers

    NY class E license and Suffolk, Nassau County and/or NYC TLC license required.


    Seeking entrepreneurial airport shuttle and limousine drivers to become drivers and ultimately owner/operator.  You will act as your own boss with Winston as your partner.  Full time owner/operator can earn up to 80k per year.  Drive the newest vehicles in the market.  Day or Night shifts are available. Benefit package available.  For more information: Click here or call 1-800-424-7767 or (631) 924-1200.

    **DISPATCHERS needed**


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