Chief Operating Officer Jobs in Chicago, IL (NOW HIRING)

Location: Markham, IL

We are seeking a strategic and results-driven Chief Operating Officer (COO) to lead and scale a national LTL/PTL transportation and cross-dock operation across multiple terminals and operational teams.

The COO will be responsible for end-to-end operational execution, network performance, service reliability, operational profitability, safety, and organizational scalability. This executive will oversee daily operations across linehaul, pickup and delivery, cross-dock operations, fleet coordination, dispatch, network planning, and operational performance management.

The ideal candidate is a hands-on operational leader with a proven track record of scaling asset-based transportation companies through disciplined execution, strong leadership, modern management systems, and data-driven decision-making.

• Lead nationwide LTL/PTL operations across multiple terminals and operational teams.

• Oversee:

  • Pickup & Delivery Operations

  • PTL Linehaul Operations

  • Cross-Dock Operations

  • Dispatch & Route Planning

  • Fleet Coordination

  • Network Performance

  • Service Recovery & Exception Management

• Drive operational excellence across safety, service, equipment utilization, and profitability.

• Develop scalable operational systems, SOPs, performance standards, and accountability frameworks.

• Optimize terminal-to-terminal network performance.

• Improve transit times, dock productivity, and route efficiency.

• Enhance customer service levels and operational reliability.

• Reduce empty miles, detention, claims, and operational waste.

• Partner with Commercial and Finance teams to maximize network efficiency and contribution margins.

• Lead regional operations leaders, terminal managers, dispatch teams, and operational managers.

• Foster a culture of accountability, ownership, collaboration, and continuous improvement.

• Mentor and develop future operational leaders.

• Align operational teams around standardized operating processes and performance expectations.

• Lead continuous improvement initiatives across:

  • Transportation Management Systems (TMS)

  • Enterprise Resource Planning (ERP)

  • Dispatch Systems

  • KPI Dashboards

  • Operational Analytics

  • Automation Projects

• Collaborate with IT and Data teams to improve operational visibility and reporting.

• Establish KPI governance and data-driven operational management.

• Own and improve key operational metrics, including:

  • Operating Ratio (OR)

  • Contribution Margin

  • On-Time Pickup & Delivery

  • Dock Productivity

  • Fleet Utilization

  • Cost per Mile

  • Claims Ratio

  • Driver Productivity

• Support operational budgeting, forecasting, strategic planning, and network expansion initiatives.

• Drive profitability through operational efficiency and disciplined execution.

• Bachelor's degree in Business, Supply Chain, Logistics, Transportation, or a related field (Master's degree preferred).

• 10+ years of progressive leadership experience within transportation or logistics operations.

• Extensive experience with:

  • Less-than-Truckload (LTL) Operations

  • Partial Truckload (PTL)

  • Cross-Dock Networks

  • Asset-Based Transportation

  • Multi-Terminal Operations

• Experience leading large dispatch, fleet, and operational teams.

• Strong understanding of transportation finance, operational KPIs, and cost management.

• Proven success in building scalable transportation operations.

• Experience scaling regional or national transportation networks.

• Experience implementing or optimizing TMS and ERP systems.

• Knowledge of Lean, Six Sigma, Continuous Improvement, or modern operational management methodologies.

• Experience with Agile, POD, or decentralized operational structures is a plus.

• Strong analytical, strategic planning, and operational problem-solving skills.

The successful candidate will:

• Demonstrate strong ownership and accountability.

• Build scalable systems and sustainable operational processes.

• Lead through execution, coaching, and performance management.

• Balance strategic vision with operational excellence.

• Thrive in fast-paced, high-growth environments.

• Drive organizational change while maintaining service excellence.

Success in this role will be measured by:

• Improved Operating Ratio (OR)

• Increased operational profitability

• Higher on-time pickup and delivery performance

• Enhanced customer satisfaction and retention

• Improved dock productivity and fleet utilization

• Reduced claims, detention, and cost per mile

• Scalable multi-terminal operational performance

• Strong leadership development and organizational accountability

• Continuous operational improvement through data-driven decision-making

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