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Oversize Load Driver Jobs in Wisconsin (NOW HIRING)

Jones Logistics

Driver Manager

Waukesha, WI · On-site

$20 - $25/hr

... oversize, and over-dimensional transportation environment. This role is the primary point of ... Maintain real-time visibility of driver status, location, and load progress * Serve as the primary ...

New

Border States Industries, Inc.

CDL Driver

Eau Claire, WI · On-site

$24 - $34/hr

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States

CDL Driver

Eau Claire, WI

$24 - $34/hr

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States

CDL Driver

Green Bay, WI · On-site

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States

CDL Driver

Eau Claire, WI · On-site

$24 - $34/hr

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States Electric

CDL Driver

Eau Claire, WI · On-site

$24 - $34/hr

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States Industries, Inc.

CDL Driver

Green Bay, WI · On-site

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States

CDL Driver - Class A

Pewaukee, WI · On-site

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States

CDL Driver - Class A

Eau Claire, WI · On-site

$24 - $34/hr

Maintains a clean vehicle, daily driver logs and daily vehicle inspection reports. Completes truck ... Rigs oversize loads to pole trailers for proper hauling on public highways * Works on construction ...

New

Border States

CDL Driver - Class A

Pewaukee, WI

Maintains daily driver logs and daily vehicle inspection reports (DVIR). * Completes truck summary ... Rigs oversize loads to pole trailers for proper hauling on public highways. * Works on construction ...

Border States

CDL Driver - Class A

Eau Claire, WI · On-site

$24 - $34/hr

Maintains a clean vehicle, daily driver logs and daily vehicle inspection reports. Completes truck ... Rigs oversize loads to pole trailers for proper hauling on public highways * Works on construction ...

Fetch

Warehouse Associate / Driver Hybrid

Middleton, WI · On-site

$19.50/hr

... oversized packages within scheduled windows to communities. The ideal candidate is driven for self ... Regularly lift and move parcels during dispatch, load up and delivery Lift parcels that weigh up to ...

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Oversize Load Driver information

See Wisconsin salary details

$20

$28

$42

How much do oversize load driver jobs pay per hour?

As of Aug 8, 2026, the average hourly pay for oversize load driver in Wisconsin is $28.86, according to ZipRecruiter salary data. Most workers in this role earn between $24.52 and $30.34 per hour, depending on experience, location, and employer.

What are some common challenges faced by oversize load drivers, and how are they managed on the job?

Oversize Load Drivers frequently encounter challenges such as navigating tight or busy roadways, adhering to varying state and local regulations, and coordinating with escort vehicles and law enforcement. To manage these obstacles, drivers rely on detailed route planning, constant communication with their support teams, and adaptability to sudden changes like weather or construction detours. Being detail-oriented and proactive helps prevent accidents and delays, ensuring the safe delivery of large or heavy cargo. Many companies also provide ongoing training and support networks to help drivers handle these unique requirements confidently.

How much do oversize load driver pilot drivers make?

Oversize load drivers typically earn between $50,000 and $80,000 annually, depending on experience, location, and the complexity of loads. Experienced drivers with specialized skills or certifications can earn higher wages, especially when hauling complex or hazardous loads. Overtime and per-mile pay can also increase overall earnings.

What is an oversize load driver?

An Oversize Load Driver is responsible for transporting large or heavy cargo that exceeds standard legal size and weight limits. They operate specialized trucks and trailers, following strict safety regulations and obtaining necessary permits for each route. These drivers work closely with escort vehicles and law enforcement to ensure safe transport. Strong driving skills, route planning, and knowledge of load securement are essential for this role.

What are the key skills and qualifications needed to thrive as an oversize load driver, and why are they important?

To thrive as an Oversize Load Driver, you need a valid commercial driver’s license (CDL), thorough knowledge of DOT regulations, and experience handling large, heavy vehicles. Familiarity with route planning software, load securement tools, and safety equipment is crucial, along with any required permits or endorsements for specialized hauls. Excellent situational awareness, attention to detail, and strong communication skills help drivers navigate complex routes and coordinate with escorts and regulatory agencies. These skills ensure the safe and legal transport of oversized loads while minimizing risks to public safety and property.

What are popular job titles related to Oversize Load Driver jobs in Wisconsin? For Oversize Load Driver jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Oversize Load Driver jobs in Wisconsin look for? The top searched job categories for Oversize Load Driver jobs in Wisconsin are:
Oversize Load Driver jobs near you
Infographic showing various Oversize Load Driver job openings in Wisconsin as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $60,021 per year, or $28.9 per hour.

Driver Manager

Jones Logistics

Waukesha, WI • On-site

$20 - $25/hr

Other

This job post has expired today. Applications are no longer accepted.

Jones Logistics rating

5.8

Company rating: 5.8 out of 10

Based on 6 frontline employees who took The Breakroom Quiz

Job description

We are seeking a highly organized and driven Driver Manager to oversee daily fleet operations within a flatbed, oversize, and over-dimensional transportation environment. This role is the primary point of contact for drivers and is responsible for ensuring safe, compliant, and efficient operations while delivering exceptional customer service.


The ideal candidate will balance driver support, operational efficiency, regulatory compliance, and profitability while promoting a strong culture of safety and accountability.


Key Responsibilities: Fleet Supervision & Driver Management

  • Supervise daily driver activity and fleet performance
  • Maintain real-time visibility of driver status, location, and load progress
  • Serve as the primary point of contact and advocate for drivers
  • Ensure timely communication with drivers (respond within 15 minutes)
  • Monitor and enforce on-time service and dispatch compliance
  • Coach drivers on safety, performance, and operational expectations
  • Address incidents, absences, and performance concerns with internal teams
  • Review telematics, in-cab camera footage, and safety alerts


Dispatch & Operational Planning

  • Plan routes and dispatch drivers for maximum efficiency and profitability
  • Coordinate flatbed, oversize, and heavy haul freight movements
  • Manage permits, route restrictions, and compliance requirements
  • Coordinate escorts, route surveys, and jurisdictional approvals
  • Ensure adherence to customer-specific requirements and job site needs
  • Maintain accurate updates in customer systems and tracking tools


Compliance & Safety

  • Enforce DOT regulations, Hours of Service, and company policies
  • Monitor driver logs, routes, and permit compliance
  • Ensure proper cargo securement for flatbed and heavy haul loads
  • Partner with Safety and Maintenance to address issues proactively
  • Promote a safety-first culture to reduce incidents and service disruptions


Payroll, Fuel & Administrative Oversight

  • Verify and approve driver payroll (mileage, detention, layover, etc.)
  • Assist with fuel planning and cost control strategies
  • Report and track maintenance concerns
  • Maintain accurate dispatch records and communication logs


Required Skills & Competencies

  • Strong knowledge of flatbed, oversize, and heavy haul operations
  • Understanding of DOT regulations and Hours of Service
  • Experience with telematics, ELDs, and safety monitoring systems
  • Excellent communication and customer service skills
  • Ability to multitask in a fast-paced, high-pressure environment
  • Strong problem-solving and organizational skills
  • Proficiency in TMS systems, spreadsheets, and customer portals


Preferred Qualifications

  • 3–5+ years of experience in transportation, dispatch, or fleet management
  • Experience with oversize/over dimensional freight and permit coordination
  • Familiarity with route planning and heavy haul regulations
  • Experience with ELD systems and in-cab camera platforms
  • Prior leadership or supervisory experience


Work Environment

  • Office-based role with frequent communication with drivers and customers
  • Fast-paced environment requiring strong decision-making skills
  • Occasional after-hours support for operations and driver needs


Why Join Us?

  • Competitive compensation
  • Opportunity to work in specialized, high-impact transportation operations
  • Growth opportunities within a dynamic and fast-paced environment
  • Strong team culture focused on safety, accountability, and performance


Pay: $20.00 - $25.00 per hour

Work Location: In person

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