Drive Away Specialist | Westborough, MA

Sweetie Boy Transportation; Westborough (MA); On-site; USD 36,000 - 52,000; Full time

Benefits offered by this job

Health insurance after 60 days

401(k)

401(k) matching

Paid time off

Paid training

Vision insurance

Job summary

Sweetie Boy Transportation in Westborough, MA is seeking Drive Away Drivers to transport vehicles dealership-to-dealership. This role does not require a CDL and offers flexible, autonomous work with competitive pay based on vehicles moved.

You will report to a local hub, use dispatch technology and GPS, and ensure safe, timely deliveries. Full-time shifts include 5 days per week with benefits after 60 days.

Qualifications

• Valid driver's license with clean driving record; minimum 5 years of safe driving.
• Must be 24 years or older.
• Ability to drive up to 11 hours per day and work shifts up to 14 hours.
• Physically capable of working in large parking lots and performing vehicle inspections.
• Must pass pre-employment drug test and background check.
• Weekly pay: $700–$900+; Commission: 50% of weekly revenue.

Responsibilities

• Pick up and deliver cars, trucks, and other vehicles to designated locations.
• Safely drive long distances (8–10+ hours per day).
• Use mobile apps, dispatch technology, and GPS for communication, vehicle assignments, and safety checks.
• Maintain a safety-first mindset and follow all driving regulations.
• Provide excellent customer service by updating dispatchers and customers on status and handoffs.

Skills

Valid driver's license

Clean driving record

5+ years driving experience

Customer service

Ability to work long shifts

GPS / dispatch software use

Tools

Dispatch software

GPS navigation

Job description

Position: Drive Away Specialist | Westborough, MA

Location: Westborough, MA

Job Id: 526

# of Openings: 1

Since 2010, Sweetie Boy Transportation has been a leading provider of automobile transportation and logistics solutions. We are currently looking for dedicated Drive Away Drivers to join our growing AutoPilot team. If you're ready to take control of your earnings and advance your career with a dynamic, forward-thinking company, we want to hear from you!

About the Role:

As a Drive Away Driver (No CDL Required), you will be responsible for picking up and delivering cars, trucks, and other vehicles to locations across the region. You’ll enjoy the freedom of the open road while working in a safe, structured environment that values your time, skills, and commitment to excellence.

Each day, you’ll begin by reporting to your designated store or hub location, interact with our customers directly, and transport vehicles safely and professionally to their destinations. This is not a freight or CDL trucking role - it’s dealership to dealership auto transport delivery. The position offers flexibility, autonomy, and the opportunity to earn competitive pay based on the number of vehicles you move.

Key Responsibilities:

• Pick up and deliver cars, trucks, and other vehicles to designated locations throughout the day (auto transport / vehicle delivery)
• Safely drive long distances (up to 8–10+ hours per day) in varying traffic and weather conditions
• Use mobile apps, dispatch technology, and GPS navigation for communication, vehicle assignments, and safety checks
• Maintain a safety-first mindset and follow all driving regulations at all times
• Provide excellent customer service by communicating clearly with dispatchers and customers regarding vehicle status, delivery schedules, and handoffs

Requirements:

• Valid driver’s license with a clean driving record (minimum 5 years’ safe driving experience)
• Must be 24 years of age or older
• Ability to drive cars, trucks, and other vehicles for up to 11 hours per day and work shifts up to 14 hours
• Physically capable of working in large parking lots, including walking, climbing stairs, bending, kneeling, and stooping to perform vehicle inspections
• Must be able to enter and exit vehicles of varying sizes and heights throughout the day
• Strong attention to detail when inspecting vehicles, checking VIN numbers, and documenting condition reports
• Safety vest must be worn at all times on company and customer property (safety-first environment)
• Must pass a pre-employment drug test (includes marijuana/THC) and background check
• Competitive Weekly Pay: $700 - $900+ per week
• Weekly Pay with Direct Deposit, after initial 2 week delay
• Commission-Based: Drivers earn 50% of the weekly revenue generated from assigned vehicles
• Shifts: Full-time, 5 day work weeks
• Health Insurance available after 60 days for full-time employees

Why Sweetie Boy Transportation?

At Sweetie Boy Transportation, we believe in growth—both for our business and for our employees. Here, you’ll find:

• Unlimited growth potential in a rapidly expanding company
• A family atmosphere where your voice and ideas are valued
• Open-door policy from ownership—your feedback truly matters!
• Cutting-edge technology to streamline your work and improve efficiency
• Safety is our top priority: We are committed to maintaining a safe work environment for all employees

• 401(k)
• 401(k) matching
• Health insurance
• Paid time off
• Paid training
• Vision insurance

Note: We have a Zero Tolerance Drug Policy, and safety is paramount in everything we do.