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Title: Director of Transportation
Company: Boston Public Schools
Location: Boston, Massachusetts
Job Status: Full-time
Job ID: 95712
Boston Public Schools seeks a Director of Transportation

Reports to: Chief of Operations

General Description of Position

The Boston Public Schools is the largest school district in Massachusetts with approximately 57,000 students and a $1.2B budget. The Office of Transportation within BPS is one of the largest departments in the district overseeing a $120M annual budget (about 10% of total district spending). On a daily basis, our 650 buses drive 45,000 miles, bringing over 30,000 students to 200 schools across the Boston area – not just Boston Public Schools but local parochial, private, and charter schools as well.

BPS seeks an innovative, ambitious, and data-driven candidate to drive performance improvements, manage a complex array of technical tasks, work strategically on district policy, and oversee all aspects of school bus transportation services for the City and the District. This leader will oversee the transformation of one of the most complex operational departments in the district.

There are five major areas of focus for this position:

Leadership and Management

Oversee and provide inspirational leadership for a department which includes 500-plus employees and several integral divisions, including customer service, routing, fleet management, compliance, finance, and bus monitors. Manage the department’s bus service vendor and undertake all related tasks, including but not limited to: holding the vendor accountable for operational effectiveness, financial efficiency, and contract compliance; meeting, as needed, with the bus drivers’ union and the vendor’s other labor groups; and serving as the district’s point of contact for any and all meaningful negotiations with the vendor. Develop and refine department policy. Institute and strengthen a department-wide culture of accountability, productivity, professionalism, appreciation, and mutual support.

Operational Efficacy Ensure all students across the city of Boston – not just BPS students, but also students attending private, parochial and charter schools – get to school safely and on time, every single day. Oversee our deep partnership with the MBTA, which serves approximately 20,000 students through the MBTA pass program. Manage the development, maintenance, and oversight of a routing system that covers 45,000 miles a day. Ensure that we have accurate lists of riders (both who is riding and what service they should receive), while processing about 200 daily address changes. Ensure that approximately 400 bus monitors are adequately distributed across all buses serving students with accommodations for monitor support. Financial Operations Ensure that our transportation contractor is spending district resources accurately and efficiently while working to remain within budget. Devise and implement financial controls and/or new practices and policies aimed at slowing the overall budgetary rate of growth. Customer Service Ensure that families are easily able to communicate with the department – both through online tools and through the transportation hotline – a hotline that receives 70,000 calls annually. Effectively communicate changes and goals of the department to non-department stakeholders, ranging from the district’s executive leadership team to school principals to parents to the Boston City Council.

Regulations and Negotiations

Possess a deep knowledge of and ensure compliance with an extensive array of federal and state laws, rules, and regulations; and effectively advocate for changes where appropriate reforms would yield positive outcomes for the department or district. Lead negotiations with several unions and act as the district’s liaison with the vendor in its labor negotiations.


Implement and oversee a strategic, systematic, and data-driven approach to the BPS transportation system to achieve safe, on-time, and reliable performance. Develop and execute against strategic plans, with clear goals and timelines, for all aspects of the department. Lead a metrics-based performance management process, in which key performance indicators will be developed and refined to measure outcomes and illuminate insights. Develop and uphold high standards for excellence and a culture of accountability, productivity, professionalism, appreciation, and mutual support. Pursue innovative process improvements throughout the operation to improve departmental efficiency and/or performance. Use applicable technology to oversee the creation of clear, concise reports that analyze and evaluate issues in easy-to-understand terms. Effectively communicate complex issues, verbally and in writing, to internal and external audiences; this may include presenting and responding to questions in public forums, while remaining mindful of the culturally and ethnically diverse populations we serve. Engage at high levels with District and City policy makers and strategic planners on transportation policy, school schedules, budgetary issues, student safety, and other policies and issues impacted by or influential to student transportation. Develop and implement standard operating procedures in compliance with applicable federal, state and local laws and regulations; provide oversight and evaluation of transportation services/practices, including contractors, and implement immediate improvements. Ensure operational excellence for nearly $100M in contracted services – including managing the bidding processes for contracted services, implementing contracts, and holding contracted partners accountable for their outcomes, according to predetermined action plans and goals. Manage operational budget processes to ensure effective and efficient use of resources, in part by working with the Finance Department to analyze and manage key cost drivers; this may require the creation of improved resource analysis and audit procedures. Use current technology proficiently and effectively (computerized routing, data analysis tools, Microsoft Office/Excel, GPS/GIS, others); implement technology improvements where needed. Perform other responsibilities as required.


Bachelor’s degree and a minimum of five years in senior leadership roles and ten or more years overall in a transportation-related field; a candidate without a bachelor’s degree will be required to have a minimum of ten years in senior leadership roles and 15 or more years overall in a transportation-related field. Experience managing within a complex unionized environment. Extensive experience managing dynamic projects in a fast-paced environment, with a demonstrated ability to manage high-level relationships with contractors and the community. Ability to prioritize, plan, execute and deliver successful outcomes across a number of operational divisions. Demonstrated expertise in developing and implementing efficient systems for transporting students, especially students with highly specialized needs, including thorough knowledge of applicable laws and regulations. Proficiency with the Microsoft Office Suite and other technology required to access and analyze transportation data, such as computer routing, dispatch applications, and GPS/GIS. Extensive data analysis skills and experience implementing data-driven performance management processes. Ability to analyze and communicate complex issues effectively, both verbally and in writing. Excellent public speaking ability, including an ability to communicate in public forums, answer questions clearly and calmly, and demonstrate sensitivity to an ethnically and culturally diverse student, family and employee population. Ability to periodically work outside the usual business hours on evenings, weekends, and as needed to respond to emergencies. Willingness to learn and adapt – we are looking for someone who is driven to continuously improve our systems. An ability to have a strong understanding of the details of our operation and an ability to explain operational details at a high level to senior district or city leadership. Current authorization to work in the United States - Candidates must have such authorization by their first day of employment


Master’s Degree, specifically in a transportation, business, operations, education, public policy, or urban-planning-relevant field. Union contract negotiations experience. Working knowledge of Versatrans routing software and Zonar GIS software. Experience with STATA, advanced Excel/VBA, SQL, and Balanced Scorecard methodologies and tools.

Terms: Managerial Tier D, 12 months, City of Boston Residency Required. Occasional weekend and evening work required.

Please refer to (under "Employee Benefits and Policies") for more information on salary and compensation. Salaries are listed by Unions and Grade/Step.

The Boston Public Schools, in accordance with its nondiscrimination policies, does not discriminate in its programs, facilities, or employment or educational opportunities on the basis of race, color, age, criminal record (inquiries only), disability, homelessness, sex/gender, gender identity, religion, national origin, ancestry, sexual orientation, genetics or military status, and does not tolerate any form of retaliation, or bias-based intimidation, threat or harassment that demeans individuals’ dignity or interferes with their ability to learn or work.

Primary Location Central Office-Transportation Salary Range 1.0 FTE Shift Type Central Office

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