Driving Jobs in Leesburg, VA — See Openings

As of September 2026, there are 60+ open driving positions in Leesburg, VA. Current pay ranges from $1,092 to $9,775 per year. Top hiring areas include Delivery Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Leesburg, VA

$4,024 - $6,899

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Leesburg, VA

$2,300 - $4,140

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Leesburg, VA

$1,820 - $3,640

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Leesburg, VA

$4,550 - $7,735

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Leesburg, VA

$2,800 - $5,000

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Leesburg, VA

$2,520 - $4,410

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Leesburg, VA

$3,920 - $6,720

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Leesburg, VA

$3,360 - $6,160

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Leesburg, VA

$2,464 - $4,224

United Parcel Service (UPS)

UPS Package Delivery Driver

Leesburg, VA

$4,320 - $8,100

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Leesburg, FL

$3,080 - $5,280

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Leesburg, FL

$2,275 - $4,095

Driving Jobs in Leesburg — FAQ

How many driving jobs are available in Leesburg, VA right now?
There are currently 60+ open driving positions in Leesburg, VA. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Leesburg?
Driving job pay in Leesburg varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Leesburg?
Yes. Many delivery driver, courier, and DSP positions in Leesburg require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Leesburg?
Driving jobs in Leesburg offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Leesburg?
Benefits vary by employer, but many driving positions in Leesburg offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Leesburg?
Your take-home pay as a driver in Leesburg depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Leesburg?
Yes, many driving positions in Leesburg are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 60+ listings above and apply directly.

Last updated: September 11, 2026