Director of Transportation

Who We AreThe 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.Who You AreMetropolis 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.What You'll DoDevelop and execute a multi-year transportation operations safety strategy aligned with organizational growth objectivesEstablish key performance indicators for fleet utilization, on-time performance, and safety incident ratesOversee day-to-day operations including dispatch, routing, scheduling, and logistics coordinationDirect fleet acquisition, maintenance, and lifecycle management programs to maximize asset uptimeManage vendor and carrier relationships while negotiating contracts for competitive pricing and serviceImplement route optimization strategies to improve efficiency and reduce environmental impactDesign and continuously improve a national Transportation Safety Management System in compliance with federal and state regulationsLead incident investigation and root cause analysis processes to drive corrective action plansServe as the primary point of contact with regulatory agencies during audits and inspectionsPartner with senior leadership and field teams to champion a proactive safety cultureWhat we're looking for5+ years of progressive experience in transportation operationsDemonstrated expertise in DOT/FMCSA regulatory compliance and commercial driver safety programsProven track record of managing large-scale fleet operationsStrong financial acumen with experience managing large departmental budgets and capital expenditure forecastProficiency with fleet management systems and transportation management systems platformValid drivers license with a clean motor vehicle recordComprehensive knowledge of 49 CFR transportation codes and relevant state statutesAbility to travel to field locations and regulatory agencies up to 30%Capability to manage on-call responses for operational emergencies outside of standard hoursExperience coordinating with legal and HR teams to address liability and risk managementExperience leveraging AI tools to transform static workflows into responsive, high-output processesWhile not required, these are a plus:Experience with DOT and State inspection managementKnowledge of sustainability initiatives, including alternative fuel vehicles or electrification strategyFamiliarity with FMCSA Safety Measurement System and Compliance, Safety, Accountability scoresExperience in autonomous vehicle managementAbility to obtain a CDL if operationally requiredWhen 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.Metropolis may utilize an automated employment decision tool (AEDT) to assess or evaluate your candidacy for employment or promotion. AEDTs are used to assist in assessing a candidate’s application relative to the required job qualifications and responsibilities listed in the job posting.As part of this process, Metropolis retains data relevant to your candidacy, including personal information, for a period that is reasonably necessary for the use of the tool. If you are hired for the position, your data may become part of your employee records.Metropolis Technologies is an equal opportunity employer. We make all hiring decisions based on merit, qualifications, and business needs, without regard to race, color, religion, sex (including gender identity, sexual orientation, or pregnancy), national origin, disability, veteran status, or any other protected characteristic under federal, state, or local law.