Director of Transportation

Metropolis • Chicago, IL

13h • Hybrid

About The Position

Metropolis is seeking a Director of Transportation to lead all aspects of transportation operations, fleet management, and organizational safety programs. In this role, you will develop and execute strategies to ensure the safe and cost-effective movement of passengers while partnering with senior leadership to build a culture of operational excellence. You will carry direct accountability for a team of safety professionals and ensure the commercial division maintains strict compliance with all federal, state, and local transportation regulations.

Requirements

• 5+ years of progressive experience in transportation operations
• Demonstrated expertise in DOT/FMCSA regulatory compliance and commercial driver safety programs
• Proven track record of managing large-scale fleet operations
• Strong financial acumen with experience managing large departmental budgets and capital expenditure forecast
• Proficiency with fleet management systems and transportation management systems platform
• Valid drivers license with a clean motor vehicle record
• Comprehensive knowledge of 49 CFR transportation codes and relevant state statutes
• Ability to travel to field locations and regulatory agencies up to 30%
• Capability to manage on-call responses for operational emergencies outside of standard hours
• Experience coordinating with legal and HR teams to address liability and risk management
• Experience leveraging AI tools to transform static workflows into responsive, high-output processes

Nice To Haves

• Experience with DOT and State inspection management
• Knowledge of sustainability initiatives, including alternative fuel vehicles or electrification strategy
• Familiarity with FMCSA Safety Measurement System and Compliance, Safety, Accountability scores
• Experience in autonomous vehicle management
• Ability to obtain a CDL if operationally required

Responsibilities

• Develop and execute a multi-year transportation operations safety strategy aligned with organizational growth objectives
• Establish key performance indicators for fleet utilization, on-time performance, and safety incident rates
• Oversee day-to-day operations including dispatch, routing, scheduling, and logistics coordination
• Direct fleet acquisition, maintenance, and lifecycle management programs to maximize asset uptime
• Manage vendor and carrier relationships while negotiating contracts for competitive pricing and service
• Implement route optimization strategies to improve efficiency and reduce environmental impact
• Design and continuously improve a national Transportation Safety Management System in compliance with federal and state regulations
• Lead incident investigation and root cause analysis processes to drive corrective action plans
• Serve as the primary point of contact with regulatory agencies during audits and inspections
• Partner with senior leadership and field teams to champion a proactive safety culture

Benefits

• healthcare benefits
• a 401(k) plan
• short-term and long-term disability coverage
• basic life insurance
• a lucrative stock option plan
• bonus plans

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 5,001-10,000 employees