🗺 Location & Operations Context
- Base city: Milwaukee, WI
- Freight ecosystem: Industrial manufacturing, steel fabrication, heavy equipment distribution
- Regional role: Great Lakes industrial corridor (WI–IL–IN–MN)
- Warehouse activity: High-density manufacturing yards and equipment staging sites
- Shift pattern: Permit-driven dispatch windows with variable departure times
📋 Job Description
- Move oversize industrial machinery between Midwest manufacturing sites
- Coordinate permit-based routing before departure
- Perform full chain securement, binders, and rigging checks
- Manage trailer staging in industrial yards and fabrication plants
- Conduct axle weight verification and pre-trip inspection routines
- Communicate with dispatch, escort vehicles, and job-site coordinators
- Handle dock and crane-assisted unloading procedures
✅ Requirements
CDL Class A
Required and valid
Experience
2+ years flatbed or heavy haul preferred
Age
21+ years old
MVR
Clean record, no major safety violations
Physical
Load securement, chaining, tarping, equipment checks
Endorsements
No endorsements required (TWIC not mandatory)
🚛 Equipment & Fleet
- Truck assignment: Peterbilt 389, Kenworth W900, Volvo VNL heavy spec
- Fleet average age: 3–6 years
- Features: Lowboy, step-deck, RGN trailers, oversize securement kits
- Transmission type: Manual and automatic mix
- Technology: GPS tracking, YMS dispatch integration, electronic logs
- Maintenance program: Scheduled preventive maintenance with rapid repair turnaround
🏠 Home Time
- Weekly or bi-weekly return based on permit cycles
- Extended runs during oversize project loads
- Reset time between heavy haul assignments
- Schedule depends on escort and routing availability
📍 Real Routes Our Drivers Take
- Milwaukee, WI → Chicago, IL (industrial machinery transfers)
- Milwaukee, WI → Madison, WI (manufacturing equipment deliveries)
- Milwaukee, WI → Indianapolis, IN (construction fleet relocations)
- Milwaukee, WI → Minneapolis, MN (heavy equipment distribution yards)
- Milwaukee, WI → Rockford, IL (fabrication and steel plant logistics)
🎁 Benefits & Bonus Structure
📝 Hiring Process
❓ Frequently Asked Questions
Is a CDL-A required?
Yes, a valid CDL Class A license is required for all heavy haul and oversize assignments.
Do I need heavy haul experience?
2+ years of flatbed or oversize freight experience is preferred but not strictly required if securement skills are strong.
What kind of physical work is involved?
Drivers perform chaining, tarping, rigging checks, and trailer inspections for oversize cargo securement.
What is the typical schedule?
Routes are permit-based and vary weekly, with some runs requiring extended regional travel.
Is overtime available?
Yes, detention time, delays, and extended haul cycles often contribute to additional weekly hours.
What equipment will I use?
Drivers operate heavy-duty tractors with lowboy, step-deck, and RGN trailers depending on load type.
💼 Career Opportunities
Drivers entering this heavy haul operation in Milwaukee typically start with regional flatbed or oversize assignments focused on equipment transport between manufacturing yards, steel fabrication facilities, and construction staging sites. As experience builds in load securement, permitting coordination, and multi-state routing, drivers transition into more complex oversize movements involving higher axle weight loads and specialized trailer configurations. With consistent performance and safety compliance, opportunities expand into lead driver roles supporting permit-sensitive freight and escort coordination. Long-term progression can lead to trainer positions, safety compliance support, or dispatch coordination roles within the heavy haul division. Some drivers later move into specialized project freight teams handling high-value industrial relocations across broader Midwest corridors. Advancement is primarily based on demonstrated securement accuracy, route compliance knowledge, and ability to manage time-sensitive delivery windows within regulated oversize transport operations.
🔗 CDL-A Heavy Haul & Oversize Flatbed Driver – Milwaukee, WI
Milwaukee’s heavy haul trucking sector supports continuous movement of industrial machinery, construction equipment, and fabricated steel components across Wisconsin and surrounding Midwest states. This regional CDL-A role operates within a structured logistics network connecting manufacturing plants, distribution yards, and construction project sites throughout Illinois, Indiana, and Minnesota. The position reflects steady demand driven by ongoing infrastructure development, industrial maintenance cycles, and equipment modernization projects. Drivers typically work with permit-based routing systems that determine schedules and travel windows, ensuring compliance with weight, height, and escort requirements. Weekly earnings range from $1,800 to $3,000 depending on load complexity and mileage cycles, with structured compensation tied to securement responsibility and operational delays. The Milwaukee freight environment remains stable due to its concentration of metal fabrication, machinery production, and construction supply chains, creating recurring oversize freight opportunities throughout the year.
🚀 Apply for This CDL-A Position
Complete the application for CDL-A Heavy Haul & Oversize Flatbed Driver in Milwaukee, WI.