Fleet Planner & Driver Success Manager

Stoughton Trailers, LLC; Stoughton (WI); On-site; USD 60,000 - 90,000; Full time

Job summary

Stoughton Trailers, LLC in Wisconsin is seeking a Fleet Planner to drive driver capacity planning, load optimization, and seamless execution across the freight network. You will develop strategic load plans, build driver relationships, and align preferences with operational needs.

The role requires 2–5+ years in fleet planning or dispatch, proficiency with TMS and Excel, and strong communication. You will monitor on-time performance, ensure DOT compliance, and collaborate with brokerage,

Qualifications

• Strong understanding of trucking operations, DOT regulations, and Hours of Service
• Proficiency in Transportation Management Systems (TMS) and Microsoft Office (Excel strongly preferred)
• Exceptional multitasking, prioritization, and problem-solving skills
• Strong analytical mindset with the ability to make data-driven decisions in real time
• Excellent verbal and written communication skills
• Ability to perform under pressure and adapt quickly to changing priorities

Responsibilities

• Develop and execute strategic load plans that maximize driver productivity and revenue per mile
• Build and maintain strong, trust-based relationships with drivers through consistent communication
• Align driver preferences (home time, routes, equipment) with operational needs
• Coach drivers on performance, Hours of Service (HOS), and operational expectations
• Plan, assign, and optimize loads to ensure efficient use of fleet capacity
• Balance service, cost, and driver satisfaction through effective decision-making
• Utilize TMS and planning tools to identify opportunities to reduce empty miles and increase utilization
• Anticipate and proactively resolve service disruptions or capacity gaps
• Monitor shipments in transit and ensure on-time pickup and delivery performance
• Track and trace loads, identifying risks and intervening before issues escal
• Communicate effectively with drivers, brokers, shippers, and internal teams
• Ensure accurate and timely documentation for all loads
• Ensure adherence to DOT regulations, including Hours of Service compliance
• Coordinate required driver compliance items (e.g., medical cards)
• Support and reinforce company safety policies and initiatives
• Monitor and manage key metrics including utilization, on-time performance, cost per mile, and revenue
• Review driver pay, accessorials, and advances for accuracy
• Identify and implement continuous improvement opportunities in planning processes
• Partner with brokerage, customer service, and supply chain teams to align capacity with demand
• Serve as a key communication hub between drivers and internal stakeholders
• Contribute to a positive, team-oriented work environment

Job description

Stoughton Trailers, LLC in Wisconsin is seeking a Fleet Planner to drive driver capacity planning, load optimization, and seamless execution across the freight network. You will develop strategic load plans, build driver relationships, and align preferences with operational needs.

The role requires 2–5+ years in fleet planning or dispatch, proficiency with TMS and Excel, and strong communication. You will monitor on-time performance, ensure DOT compliance, and collaborate with brokerage,