Top 553 Otr Jobs in Greenfield, Wi

CDL A OTR Truck Driver – Milwaukee OTR Division
DSL Express —Milwaukee, WI
- $1,900 - $2,700 a week
- Online Application
- Clean driving record
- No touch freight
- Pass drug screening
- Fuel card
Quick Apply
CDL A Reefer Teams - OTR
Decker Truck Line, Inc. —Wisconsin
- $165,000 - $180,000 a year
- No weekends
- DOT physical examination
- CDL A
- Mid-level
- Passenger ride along program
- Disability insurance
Quick Apply
12d
OTR CDL-A Truck Driver -$5000 Sign-On!
Blackhawk —Milwaukee, WI
- $100,000 a year
- Online Application
- Dedicated
- Clean driving record
- CDL A
- Paid training
- Paid holidays
Quick Apply
OTR CDL-A Truck Driver -$5000 Sign-On!
Blackhawk —Milwaukee, WI
- $100,000 a year
- Online Application
- Dedicated
- Clean driving record
- CDL A
- Paid training
- Paid holidays
Quick Apply
CDL A OTR Lease Purchase Truck Driver
Windy City National Trans Inc —Wisconsin
- $500 - $10,000 a week
- No touch freight
- Dry van
- Mid-level
Quick Apply
12d
CDL OTR Temporary Driver, possible Full-Time Potential (AM Shift)
Arandell —Menomonee Falls, WI
- $30.50 an hour
- Full-time
- Mid-level
- 3 years
- OTR
Quick Apply
7d
OTR Driver
Michels Corporation —Franksville, WI
- Clean driving record
- Hazmat Endorsement
- CDL A
- Health savings account
- Disability insurance
OTR Truck Driver
The Scotts Miracle-Gro Company —Germantown, WI
- $32.35 - $41.90 an hour
- Full-time
- CDL A
- Mid-level
- 3 years
- Health insurance
- Dental insurance
OTR Driver
ScottsMiracle-Gro —Germantown, WI
- $32.35 - $41.90 an hour
- Full-time
- CDL A
- Mid-level
- 3 years
Quick Apply
CDL A OTR Truck Driver-Auto Transport-We Train
Countryside Auto Transport Inc. —Wisconsin
- $85,000 - $115,000 a year
- Full-time
- CDL A
- Mid-level
- High school diploma or GED
- Paid training
- Passenger ride along program
Quick Apply
CDL A Driver Company Flatbed Step Deck
Kaiser Transport, Inc. —Wisconsin
- $0.68 - $0.73 per mile
- CDL A
- Mid-level
- Math
- Passenger ride along program
- Health insurance
Quick Apply
12d
Class A Owner - Operator OTR Driver
DSL Express —Milwaukee, WI
- $312,000 - $460,000 a year
- Choose your own hours
- Clean driving record
- Owner-operator
- No touch freight
- Passenger ride along program
- Fuel card
Quick Apply
CDL A Truck Driver-Midwest Regional/OTR
Xtreme Trucking, LLC —Wisconsin
- $0.65 - $0.72 per mile
- Owner-operator
- CDL A
- Mid-level
- Passenger ride along program
- Disability insurance
Quick Apply
12d
OTR Class A CDL Truck Driver
LCL Bulk Transport, Inc. —Racine, WI
- From $0.66 per mile
- Call employer
- Clean driving record
- DOT physical examination
- Pass drug screening
- Paid training
- Paid holidays
Quick Apply
CDL-A Truck Driver - Flatbed Division - 1 Year Experience Required
Koch Trucking —Milwaukee, WI
- $88,000 - $98,000 a year
- Online Application
- CDL A
- Mid-level
- Flatbed truck
- Passenger ride along program
- Disability insurance
Quick Apply
CDL A Truck Driver - Dedicated - CO
Swift Transportation Co. of Arizona LLC —Milwaukee, WI
- $0.50 per mile
- Dedicated
- Clean driving record
- DOT physical examination
- Wellness program
- AD&D insurance
Quick Apply
12d
CDL A W2 OTR Company Driver +Benefits
JS Helwig and Son LLC —Wisconsin
- $0.55 - $0.65 per mile
- CDL A
- Mid-level
- Clean MVR report
- Passenger ride along program
- Health insurance
Quick Apply
1d
CDL A OTR Flatbed Company Truck Driver
TAG TRANS INC —Wisconsin
- $0.65 per mile
- Clean driving record
- CDL A
- Mid-level
- Passenger ride along program
- Disability insurance
Quick Apply
12d
OTR Driver Class A Truck Driver – Oversize/Over-Dimensional Freight
Transport National —Oak Creek, WI
- From $1,300 a week
- Full-time
- DOT physical examination
- Pass drug screening
- CDL A
- Paid training
- Fuel card
Quick Apply
CDL A OTR Regional Truck Driver
Beacon Transport —Milwaukee, WI
- $0.60 - $0.62 per mile
- Clean driving record
- No touch freight
- Dry van
- Passenger ride along program
- Health savings account
Quick Apply
12d

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CDL A OTR Truck Driver – Milwaukee OTR Division

DSL Express -
Milwaukee, WI

Quick Apply

Job Details

Full-time
$1,900 - $2,700 a week

Benefits

Fuel card

Qualifications

CDL A
DOT Physical Certification
Long-haul driving experience

Full Job Description

We are actively hiring experienced Class A CDL Solo OTR Truck Drivers for our modern fleet who live in the Milwaukee, WI area and nearby communities. Milwaukee stands as one of our important Midwest hubs with steady freight movement. Routes frequently begin or conclude near this region, providing drivers from the local area with dependable home time on long-haul nationwide operations.

Typical Pay Highlights:

30% of line haul OR 65 a mile + bonuses (the choice most solo drivers prefer).
Average weekly gross: $1,900 – $2,400 (with peaks reaching $2,700+ on legal hours).
Switch between percentage and miles pay whenever you choose.
Full-time floor in 2025 was $104,130 — no steady driver earned less.
Top performers reached $145,000 last year.
Anyone who wants to put in the effort will make good money.

Pay Details & Realistic Expectations:
Pay is 100% performance-based. In 2025, 87% of our drivers went with the 30% percentage plan because it consistently delivered better earnings in the current market. Slow season (Q1) typically ranges from $1,900–$2,100 per week with some weeks hitting $2,400. Peak seasons (Q2 and Q4) usually run $2,100–$2,400 with some $2,700 weeks. Q3 is somewhere between. Consistent drivers earned between $115,000 and $125,000 in 2025. This seasonal pattern has been reliable for the past 25 years.

Pay Options:

Percentage Pay (Best Option for Most Solos) - We pay up to 30% of line haul plus bonuses. We intentionally keep miles lower on percentage (2,000–2,500 in slow season and up to 3,000 in busy season) because it maximizes take-home pay, lowers fuel costs, and helps avoid burnout.
Miles Pay Option - Switch at any time. Up to 65 cents per mile plus bonuses based on experience and record. Typical miles: 2,500–3,600 per week.
Team Pay (Miles Only) - Up to 75¢ per mile split. Average $2,000–$2,600 per driver per week. Note: Solo percentage pay is currently the stronger choice in this market.

Apply here and get approved faster — https://www.dslfreight.com/join-our-team/.

Important Info About Our Work Ethic:
We receive a high volume of applications and are very selective — we only want “A” stringers and true professionals. Honest, motivated, and hard-working drivers earn excellent money and are treated like family. If you prefer taking it easy, missing loads, or spending excessive time at truck stops, this opportunity is not the right fit. We are fair, but results come from effort. This is OTR driving.

Sound harsh? Good. The truth matters. We still miss the veteran drivers who left after the 2019 ELD mandate. Respect to everyone still out here grinding.

Still here? Great — Here’s the link again: https://www.dslfreight.com/join-our-team/.

What Makes DSL Express Different:

We are a well-established company with 25 years in business since 2001 — large enough to deliver strong support and resources, yet small enough that every driver counts.
We welcome veterans and offer fair-chance employment to anyone ready to work hard.
24/7 dispatch from three offices with real experienced staff.
Modern trucks (mostly automatics with some manuals available) equipped with fridges and inverters.
Company-owned mechanic shops in Chicago and Las Vegas.
Dedicated dispatchers who learn your style and preferences.
All no-touch freight in dry van or reefer trailers.
Strong carrier partnerships that combine big-company capabilities with a family-owned atmosphere.

Perks:

No forced dispatch.
Ability to take the truck home during hometime with parking support.
Fuel cards and EZ-Passes provided.
Weekly direct deposit.
Flexible and reliable home time.
Hazard occupational insurance covering lost wages, medical, and beneficiary.
Monthly bonuses for safety, delivery performance, and communication.
Additional bonuses for successful DOT inspections.

Job Description:

Class A CDL required (additional endorsements a plus).
Minimum 2+ years verifiable CDL experience.
Clean MVR and acceptable PSP report.
Dry van or reefer — all no-touch freight.
Must be comfortable with modern ELD systems and able to pass pre-employment drug screen.

Minimum Driver Qualifications:

Must be physically fit and prepared for the demands of over-the-road driving.
Valid Class A CDL with no pending suspensions.
Up-to-date valid medical card.
No failed or refused drug/alcohol tests in the last 4 years.
No DWI, DUI, or BAC convictions in the last 4 years.
No reckless driving convictions in the last 3 years.
No more than 3 moving violations or accidents in the last 3 years.
No license suspension for points or unpaid tickets in the last 3 years.
No more than 2 moving violations in the past year.
At least 3+ years of verifiable work history (including non-driving time).

We want serious, good people who take this job seriously. If that’s you, apply today — https://www.dslfreight.com/join-our-team/.

About DSL Express:

WE'VE BUILT A REPUTATION ON EXCELLENCE IN SHIPPING AND LOGISTICS... DSL Express is a family-owned company with 25+ years in the Midwest, West Coast, and East Coast. We’re part of a federation of 5 companies with ~500 trucks total and 60+ years of combined experience. We have strong relationships with Chicago shippers/brokers and partners nationwide/Canada. Our experienced dispatchers (10+ years average) keep a low ratio (~5 trucks per dispatcher) so they can focus on you — flexible home time, the loads/miles you want, and support when needed. Yard parking, mechanic shops, and warehouses in Chicago + Las Vegas offices make life easier. Visit www.dslfreight.com or call 888-602-1140 x140 to learn more!

Quick Apply

Refine Your Search

otr jobs in greenfield, wi

CDL A OTR Truck Driver – Milwaukee OTR Division

CDL A Reefer Teams - OTR

OTR CDL-A Truck Driver -$5000 Sign-On!

OTR CDL-A Truck Driver -$5000 Sign-On!

CDL A OTR Lease Purchase Truck Driver

CDL OTR Temporary Driver, possible Full-Time Potential (AM Shift)

OTR Driver

OTR Truck Driver

OTR Driver

CDL A OTR Truck Driver-Auto Transport-We Train

CDL A Driver Company Flatbed Step Deck

Class A Owner - Operator OTR Driver

CDL A Truck Driver-Midwest Regional/OTR

OTR Class A CDL Truck Driver

CDL-A Truck Driver - Flatbed Division - 1 Year Experience Required

CDL A Truck Driver - Dedicated - CO

CDL A W2 OTR Company Driver +Benefits

CDL A OTR Flatbed Company Truck Driver

OTR Driver Class A Truck Driver – Oversize/Over-Dimensional Freight

CDL A OTR Regional Truck Driver

I want to receive the latest job alert for otr in greenfield, wi

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