Oversize Permit Jobs in Wisconsin (NOW HIRING)

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