Driver Operations Supervisor | Trucking & Fleet Operations

DSV • Itasca, IL

7d • $70,000 - $80,000 • Onsite

About The Position

DSV is looking for a Supervisor, Driver Operations, to lead and support a team of company drivers while helping keep our transportation operation safe, efficient, compliant, and on schedule. This is a hands-on leadership role for someone who understands the realities of trucking operations and knows how to balance people leadership, driver utilization, service performance, and DOT compliance. You’ll oversee day-to-day driver operations, including scheduling, route execution, Hours of Service, performance, and operational support. When traffic, weather, equipment, staffing, or other challenges affect the plan, you’ll work with drivers and internal teams to make adjustments, solve problems, and keep freight moving safely and efficiently. Just as importantly, you’ll lead the people behind the operation. You’ll coach and develop drivers, set clear expectations, address performance concerns, reinforce safety and compliance, and help create a team culture built around accountability, communication, and strong performance. If you bring transportation or driver operations experience and are ready to take ownership of a fast-moving operation while developing a strong driver team, this is an opportunity to grow your leadership career with the world’s largest freight forwarding and logistics company.

Requirements

• High school diploma or GED required.
• 1 to 3 years of experience in transportation operations, trucking, fleet management, logistics, or a related operational environment.
• Working knowledge of Department of Transportation (DOT) regulations, Hours of Service requirements, and transportation compliance.

Nice To Haves

• Bachelor's degree in Logistics, Supply Chain Management, Transportation, Business, or a related field preferred; equivalent industry experience may be considered in lieu of a degree.
• Minimum of 1 year of supervisory, team leadership, or driver management experience preferred.
• Experience supervising or supporting company drivers in a transportation environment strongly preferred.
• Experience with driver scheduling, dispatch, route management, or transportation operations preferred.
• Experience working with Transportation Management Systems (TMS), dispatch systems, or related transportation technology preferred.
• Strong leadership and people-management skills with the ability to coach, support, and hold drivers accountable for established expectations.
• Strong understanding of driver operations, dispatch, scheduling, route execution, and transportation workflows.
• Strong organizational and problem-solving skills with the ability to manage multiple drivers, routes, and operational priorities simultaneously.
• Ability to respond effectively to time-sensitive transportation issues and make sound operational decisions.
• Strong analytical skills with the ability to evaluate driver and operational performance and identify opportunities for improvement.
• Strong written and verbal communication skills with the ability to work effectively with drivers, operations teams, customer service, and leadership.
• Results-oriented approach with a strong commitment to safety, service quality, on-time performance, and operational efficiency.
• Proficiency in Microsoft Office applications, including Excel, Word, and PowerPoint.
• Experience working with Transportation Management Systems (TMS), dispatch systems, and operational technology platforms preferred.

Responsibilities

• Supervise and provide day-to-day leadership to company drivers, establishing clear expectations for safety, performance, service, attendance, and operational execution.
• Monitor driver performance and provide regular coaching, feedback, recognition, and appropriate accountability to support employee development and operational performance.
• Conduct performance reviews and address performance concerns in accordance with company policies and procedures.
• Support driver onboarding, training, development, engagement, and retention.
• Conduct regular driver meetings focused on safety, compliance, operational updates, performance expectations, and team communication.
• Foster a collaborative team environment that promotes safety, accountability, professionalism, and high performance.
• Coordinate daily driver assignments, schedules, and transportation activities based on freight requirements, driver availability, Hours of Service, and operational priorities.
• Maintain regular communication with drivers while they are on the road and provide support for issues that may impact safety, service, scheduling, or route completion.
• Monitor driver availability, route progress, Hours of Service, traffic, weather, equipment availability, and other operational conditions and adjust plans as necessary.
• Review and optimize transportation routes to support on-time performance, effective driver utilization, fuel efficiency, and reduction of unnecessary or deadhead miles.
• Address driver and transportation-related operational issues and ensure timely resolution or escalation when appropriate.
• Collaborate with operations, customer service, and other internal teams to address delivery concerns, service failures, and changing transportation requirements.
• Provide training and guidance to drivers on company technology platforms, transportation systems, operational procedures, and documentation requirements.
• Review and approve operational documentation, reports, driver records, and other required information.
• Ensure drivers comply with applicable DOT regulations, federal and state transportation requirements, company safety policies, and established operational procedures.
• Monitor driver and transportation performance to identify safety, service, compliance, utilization, and productivity trends or concerns.
• Support corrective actions and improvement initiatives designed to strengthen safety, service quality, driver utilization, and operational efficiency.
• Promote safe driving practices and reinforce expectations related to vehicle inspections, Hours of Service, required documentation, and other transportation compliance requirements.
• Utilize Transportation Management Systems (TMS), dispatch tools, and related technology to monitor driver operations, route performance, and operational activity.
• Support continuous improvement initiatives and identify opportunities to improve processes, productivity, service delivery, and overall transportation performance.
• Perform additional duties, responsibilities, and projects as assigned to support business operations

Benefits

• Information regarding DSV’s benefits offerings, including eligibility, coverage options, and plan details, is available through the DSV Benefits Showcase.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: High school or GED