Director of Transportation

The real world is the next frontier, and at Metropolis, we are creating the artificial intelligence to make it responsive. We are pioneering the Recognition Economy — a future where mundane repetition disappears and being known unlocks access, comfort, and belonging everywhere you go. From transforming parking into a seamless drive-in, drive-out experience for millions of Members to expanding our intelligence layer across retail and hospitality, we are building a world that feels instinctive and magical. The future isn’t coming; it’s here, and we need builders, innovators, and problem solvers to help us create it.

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.

• →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

• 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

• 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

When you join Metropolis, you'll join a team of world-class product leaders and engineers, building an ecosystem of technologies at the intersection of parking, mobility, and real estate. Our goal is to build an inclusive culture where everyone has a voice and the best idea wins. You will play a key role in building and maintaining this culture as our organization grows. The anticipated base salary for this position is $120,000.00 USD to $130,000.00 USD annually. The actual base salary offered is determined by a number of variables, including, as appropriate, the applicant's qualifications for the position, years of relevant experience, distinctive skills, level of education attained, certifications or other professional licenses held, and the location of residence and/or place of employment. Base salary is one component of Metropolis' total compensation package, which may also include access to or eligibility for healthcare benefits, a 401(k) plan, short-term and long-term disability coverage, basic life insurance, a lucrative stock option plan, bonus plans, and more. #LI-DL1 #LI-Onsite