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Small Fleet jobs in Waukesha, WI

There are 129 Small Fleet jobs available TODAY in Waukesha, Wisconsin on Lanefinder. Apply now for your next great CDL job!

1099 Class A Dry Van (Cover Travel & No SAP)
V & D TRANSPORTATION INC
10 Truck Operation Hiring in 53189
Actively Hiring
$2,000 - $2,500 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $2,000 - $2,500 gross total weekly pay
  • 14 - 21 expected days out
1099 Class A Dry Van (Cover Travel & No SAP)
V & D TRANSPORTATION INC
10 Truck Operation Hiring in 53189
Actively Hiring
$2,000 - $2,400 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $2,000 - $2,400 gross total weekly pay
  • 14 - 21 expected days out
BROTHERS FREIGHT TRANSPORT LLC logo
OVER THE ROAD -NOT LOCAL-1099 position
BROTHERS FREIGHT TRANSPORT LLC
8 Truck Operation Hiring in 53189
Actively Hiring
$1,750 - $2,275 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Refrigerated and Dry Van
  • $1,750 - $2,275 gross total weekly pay
  • 14 - 21 expected days out
MIG TRANSPORTATION INC logo
OTR Truck Driver
MIG TRANSPORTATION INC
4 Truck Operation Hiring in 53189
Actively Hiring
$2,500 - $3,000 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Flatbed trailer
  • $2,500 - $3,000 gross total weekly pay
  • 14 - 21 expected days out
CDL A, OTR, 1099
Gold Line Group
6 Truck Operation Hiring in 53189
Actively Hiring
$1,500 - $1,800 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Flatbed trailer
  • $1,500 - $1,800 gross total weekly pay
  • 14 expected days out
W2 Consistent Freight OTR
CARGO SPRINT LLC
5 Truck Operation Hiring in 53189
Actively Hiring
$1,800 - $2,600 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Flatbed trailer
  • $1,800 - $2,600 total weekly pay
  • 14 - 21 expected days out
1099 Class A Dry Van (Cover Travel & No SAP)
V & D TRANSPORTATION INC
10 Truck Operation Hiring in 53189
Actively Hiring
$2,000 - $2,400 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $2,000 - $2,400 gross total weekly pay
  • 14 - 21 expected days out
OTR CDL A Solo
Forest Brook Trucking LLC
10 Truck Operation Hiring in 53189
Actively Hiring
$1,400 - $1,800 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Hopper Bottom
  • $1,400 - $1,800 total weekly pay
  • 5 - 14 expected days out
OTR Hopper Driver
Forest Brook Trucking LLC
10 Truck Operation Hiring in 53189
Actively Hiring
$1,400 - $1,800 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Hopper Bottom
  • $1,400 - $1,800 total weekly pay
  • 5 - 6 expected days out
Over The Road 1099 Refrigerated
HAYER CARGO INC
9 Truck Operation Hiring in 53189
Actively Hiring
$2,000 - $2,200 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Refrigerated
  • $2,000 - $2,200 gross total weekly pay
  • 7 - 14 expected days out
J&Z MOVE SMART LLC logo
OTR DRIVER
J&Z MOVE SMART LLC
8 Truck Operation Hiring in 53189
Actively Hiring
$1,800 - $2,400 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $1,800 - $2,400 gross total weekly pay
  • 25 - 30 expected days out
OTR Dry Van
WINNERS TRANSPORTATION LLC
250 Truck Operation Hiring in 53189
Actively Hiring
$2,100 - $2,450 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $2,100 - $2,450 gross total weekly pay
  • 21 - 28 expected days out
J&Z MOVE SMART LLC logo
Dry van/ Flatbed / Conestoga
J&Z MOVE SMART LLC
8 Truck Operation Hiring in 53189
Actively Hiring
$1,800 - $3,000 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Live Haul, Power Only, Dry Van and Flatbed trailer
  • $1,800 - $3,000 gross total weekly pay
  • 14 - 21 expected days out
OTR 1099 Dry Van
ZAIETS TRANSPORTATION LLC
3 Truck Operation Hiring in 53189
Actively Hiring
$1,950 - $2,500 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $1,950 - $2,500 gross total weekly pay
  • 21 - 28 expected days out
OTR, 1099 Solo
Rightlane Express
7 Truck Operation Hiring in 53189
Actively Hiring
$1,620 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Power Only and Refrigerated
  • $1,620 gross total weekly pay
  • 5 - 7 expected days out
OTR Reefer
WINNERS TRANSPORTATION LLC
250 Truck Operation Hiring in 53189
Actively Hiring
$2,250 - $2,625 per week
Owner Operator (O/O)
OTR
  • Class A OTR Owner Operator Refrigerated
  • $2,250 - $2,625 gross total weekly pay. Paid weekly
  • Home at least one weekend.
West Logistics LLC logo
CDL-A OTR REEFER DRIVER
West Logistics LLC
10 Truck Operation Hiring in 53189
Actively Hiring
$1,500 - $3,000 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Refrigerated
  • $1,500 - $3,000 gross total weekly pay
  • 28 - 60 expected days out
Bountiful Trucking LLC logo
W2 with Benefits - Reefer Freight, Over the Road
Bountiful Trucking LLC
10 Truck Operation Hiring in 53189
Actively Hiring
$1,500 - $1,800 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Refrigerated
  • $1,500 - $1,800 total weekly pay
  • 12 - 14 expected days out
O/O OTR Position
ZAIETS TRANSPORTATION LLC
3 Truck Operation Hiring in 53189
Actively Hiring
$9,600 - $15,000 per week
Owner Operator (O/O)
OTR
  • Class A OTR Owner Operator Dry Van
  • $9,600 - $15,000 gross total weekly pay. Paid weekly
  • Home at least one weekend.
Flatbed OTR
WINNERS TRANSPORTATION LLC
250 Truck Operation Hiring in 53189
Actively Hiring
$2,400 - $2,800 per week
Owner Operator (O/O)
OTR
  • Class A OTR Owner Operator Flatbed trailer
  • $2,400 - $2,800 gross total weekly pay. Paid weekly
  • Home at least one weekend.
Bountiful Trucking LLC logo
OTR, W2 with Benefits - Reefer Freight
Bountiful Trucking LLC
10 Truck Operation Hiring in 53189
Actively Hiring
$1,500 - $1,800 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Refrigerated
  • $1,500 - $1,800 total weekly pay
  • 14 expected days out
OTR Dolo driver
Rightlane Express
7 Truck Operation Hiring in 53189
Actively Hiring
$1,800 - $2,600 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Dry Van
  • $1,800 - $2,600 gross total weekly pay
  • 30 - 35 expected days out
Triumph Transport LLC logo
1099 OTR Flatbed ($3300/week minimum)
Triumph Transport LLC
4 Truck Operation Hiring in 53189
Actively Hiring
$2,900 - $3,000 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Flatbed trailer
  • $2,900 - $3,000 gross total weekly pay
  • 7 - 14 expected days out
General Freight (Hazmat available too w/ good pay)
KIK LLC
70 Truck Operation Hiring in 53189
Actively Hiring
$1,600 - $2,450 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Refrigerated and Dry Van
  • $1,600 - $2,450 gross total weekly pay
  • 14 - 21 expected days out
DGL Transportation INC logo
Stepdeck driver
DGL Transportation INC
5 Truck Operation Hiring in 53189
Actively Hiring
$1,500 - $3,000 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Step Deck
  • $1,500 - $3,000 gross total weekly pay
  • 1 - 2 expected days out
Triumph Transport LLC logo
Owner Operator Flatbed ($11,000-$13,000/wk)
Triumph Transport LLC
4 Truck Operation Hiring in 53189
Actively Hiring
$11,000 - $13,000 per week
Owner Operator (O/O)
OTR
  • Class A OTR Owner Operator Step Deck and Flatbed trailer
  • $11,000 - $13,000 gross total weekly pay. Paid weekly
  • Home at least 2 weekends.
OTR / Regional CDL Truck Driver - 1099 - Flexible Home Time
Freightwave Transport
1 Truck Operation Hiring in 53189
Actively Hiring
$1,800 - $2,200 per week
Contracted Driver (1099)
Regional
  • Class A Regional Contract Driver (1099, Solo) Dry Van
  • $1,800 - $2,200 gross total weekly pay. $2,000 sign on bonus
  • 4 - 6 expected days out
OTR - New Trucks & Consistent Miles (No SAP)
GREEN WAY TRANSPORT LLC
5 Truck Operation Hiring in 53189
Actively Hiring
$1,700 - $2,200 per week
Contracted Driver (1099)
OTR
  • Class A OTR Contract Driver (1099, Solo) Refrigerated and Dry Van
  • $1,700 - $2,200 gross total weekly pay
  • 10 - 14 expected days out
OTR Flatbed - American Owned Family Business
SIGMA SQUARED TRANSPORT CORPORATION
2 Truck Operation Hiring in 53189
Actively Hiring
$1,500 - $4,000 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Flatbed trailer and Step Deck
  • $1,500 - $4,000 total weekly pay. $1,500 sign on bonus
  • 21 - 30 expected days out
Global paving logo
Dump Truck Driver
Global paving
3 Truck Operation Hiring in 53189
Actively Hiring
$1,200 - $1,500 per week
Direct Employment (W2)
OTR
  • Class A OTR Company Driver (W2, Solo) Dump Truck
  • $1,200 - $1,500 total weekly pay
  • 5 - 6 expected days out

1099 Class A Dry Van (Cover Travel & No SAP)

V & D TRANSPORTATION INC
$2,000 - $2,500 per week
Contracted Driver (1099)
OTR
  • Dry van
  • Contract Driver (1099)
  • No Driver Load/Unload
  • 3 days off for every 14 days worked
Hiring Requirements
  • Class A license without any of the following restrictions: (L,Z) Air Brakes, (G) Night Driving, (O) No Semi Trailer or (K) Intrastate Only
  • 2 years Tractor Trailer experience
  • No more than 1 moving violation in the last year
  • No more than 1 moving violation in the last 3 years
Pay & Miles
  • $2,000 - $2,500 gross total weekly
  • $0.65 - $0.7 CPM
  • 3,000 - 3,500 miles per week
Home Time
  • 3 days off for every 14 days worked
  • 14 - 21 expected days out
  • You can stay out longer if you want to
  • Home at least one weekend per month
Freight Handling
  • 100% live load / unload
Carrier and Truck Information
  • Fleet size: 10 trucks
  • Semi-trucks are governed at 72 mph
  • Volvos, Freightliners
  • Mostly automatic semi-trucks
  • We mainly operate late model trucks
  • Truck equipment: Refrigerator, Microwave
  • No driver-facing cameras
Additional Information
  • Can take truck home
  • We're an equal opportunity employer
Pet and Rider Policy
  • Pets are not allowed
  • Riders are not allowed
Orientation Details
  • Paid orientation
  • Accommodation costs covered
  • Travel expenses covered
About the job
We are looking for reliable, safety-focused drivers who take pride in their work. Our team values clear communication, on-time service, and professionalism. Drivers can expect consistent freight, supportive dispatch, and a company that respects their time on the road. We prioritize safe operations, accurate paperwork, and strong customer service. If you're dependable, motivated, and ready to be part of a growing team, we'd love to hear from you.
Terminal pin
Terminal or Office Location

V & D TRANSPORTATION INC

10 truck operation

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