Position Type:

Administration and Professionals

Date Posted:

2026-01-06

Location:Ridge Road Depot

INTRODUCTION: CONTEXT AND MISSION

The Cleveland Metropolitan School District (CMSD) serves approximately 37,000 students in 100+ schools. Over the past several years, the Greater Cleveland community has united behind the collective goal of ensuring every child in Cleveland attends a high-quality school and every neighborhood has a multitude of great schools from which families can choose. The Cleveland Plan defines CMSD’s approach to the reinvention of public education and holds our community accountable for the success of Cleveland’s schoolchildren. The Cleveland Plan is supported by Ohio House Bill 525, which provides much-needed flexibility and autonomy for the district and its schools. Our schools have autonomy over human and financial resources in exchange for accountability for

performance. The principal has primary responsibility and accountability for establishing his or her school as a high-quality, high-expectations academic center with a focus on personalized instruction, professional support for teachers, and school-wide practices that lead to measurable results.

The Cleveland Metropolitan School District has developed standards of excellence that the district applies to all parts of the organization inclusive of schools, principals, school leadership teams, networks, and central office. Alignment between Standards of Excellence (SoE) and the district’s Theory of Action helps ensure that principals are able to focus on scholar achievement and that central office supports are timely and effective.

Our Vision for Learning in a Post-Pandemic World:

In our pursuit of a more fair, just, and good system of education, we want each of our learners, both each of our scholars and each of their educators, to be individually and collectively presented with academically / intellectually complex tasks that are worthy of their productive struggle and allow them authentic opportunities to demonstrate their work and their learning of academic content and transferable skills in a joyful and adventurous environment.

THE OPPORTUNITY:

Location: Administration or As Assigned
Reports to: Chief of District Operations
FLSA Status: Exempt
Salary Band: 12
Compensation: $ 121,410.00 - $ 157,833.00

The Executive Director of Transportation Services is responsible for managing daily transit operations for CMSD students, vehicle management, and vehicle services. Key responsibilities involve supervising staff, vehicle deployment, ensuring adherence to schedules, enforcing departmental policies, conducting disciplinary hearings, and effectively communicating procedures and guidelines. This position provides leadership to staff members with the goal of enhancing service delivery, addressing safety and public inquiries, supporting customer service initiatives, and overseeing department scheduling service in alignment with collective bargaining agreements. The role significantly contributes to organizational strategic planning and execution, requiring comprehensive knowledge of industry standards, operational trends, and providing advisory support to the Chief of District Operations on strategic matters. Additionally, the Executive Director collaborates with executive leadership to drive organizational growth, improve operational efficiency, and cultivate a culture of innovation. In addition, this position provides executive oversight of transportation-related financial planning, regulatory compliance, and long-range operational strategy. The Executive Director is responsible for aligning transportation services with District priorities, fiscal accountability, and state requirements while ensuring safe, efficient, and reliable service delivery for all students.

Essential Responsibilities:

Supervise and coordinate the activities of dispatch personnel within the Transportation Department.
Cultivate a collaborative team environment by fostering motivation and providing active support for the development and mentorship of team members.
Ensure all staff receive thorough training, have a clear understanding of their responsibilities, and consistently adhere to operational standards to maintain organizational stability.
Conduct research and implement industry best practices related to computer-aided dispatch systems and staffing requirements.
Establish key performance indicators (KPIs) for staff to improve service delivery, work performance, and accountability.
Oversee disciplinary proceedings regarding department infractions, attendance issues, violations of collective bargaining agreements, and preliminary accident investigations as necessary.
Represent the District in arbitration hearings and other labor or union-related matters as assigned.
Oversee technology initiatives and projects across transportation operations.
Provide training on the technology and equipment utilized by dispatchers and supporting staff.
Review transit system route schedules to identify areas for improvement and work with stakeholders to find ways to enhance service quality.
Conduct weekly evaluations of route performance, assigning staff or working collaboratively to analyze and address negative trends.
Prepare timely and accurate reports and data concerning dispatch operations, system performance, workforce management, and other business functions as required.
Ensure prompt and accurate entry of transit system data into designated databases and reporting platforms from staff members.
Review facility inspections at remote division sites and coordinate with stakeholders to address issues, including facility upgrades, tools, supplies, and equipment requirements.
Develop, manage, and monitor the Transportation Services operating and capital budgets in collaboration with District finance and procurement staff.
Oversee expenditures related to staffing, fleet operations, fuel, maintenance, contracted transportation services, equipment, and technology systems.
Prepare financial forecasts, budget projections, and expenditure analyses to support executive decision-making.
Identify cost efficiencies and resource optimization opportunities while maintaining service quality and compliance requirements.
Make sure employees follow safety rules and safe work practices.
Remain knowledgeable of and adhere to all relevant safety and health regulations and safe working practices.
Provide guidance on safety policies and emergency procedures for bus operators and operations staff as needed.
Ensure departmental compliance with applicable Ohio Revised Code (ORC), Ohio Administrative Code (OAC), Ohio Department of Education and Workforce (ODEW) requirements, and District policies governing pupil transportation.
Oversee internal compliance reviews, corrective actions, and documentation related to driver qualifications, routing practices, fleet operations, and safety standards.
Lead long-range transportation planning efforts, including service design, staffing models, fleet replacement strategies, and operational scalability to support districtwide initiatives.
Supervise and support an individual contributor, fostering their professional development and ensuring high-quality output.
Conduct regular performance evaluations and provide constructive feedback to both the team managers and the individual contributors.
Facilitate communication and collaboration between the team managers and the individual contributors to ensure cohesive and efficient operations.
Establish and maintain effective working relationships with District employees, customers, vendors, and others, utilizing principles of excellent customer service.
Communicate clearly, effectively, and respectfully both orally and in writing.
Perform additional related duties as assigned.
Maintain regular and reliable attendance and performance.

Required Knowledge, Skills, and Abilities:

Candidates must demonstrate a comprehensive understanding of operating policies, rules, and regulations related to transit services. This includes familiarity with transit routes, equipment utilized within the system, and established schedules for service delivery. A thorough knowledge of both urban and suburban transit operations is essential.
Candidates should be able to navigate and address the unique challenges and requirements associated with varying service areas.
Proficiency in labor relations is required, specifically in the administration of labor agreements and contracts. This includes understanding the processes involved in resolving labor issues and applying relevant policies.
Candidates must possess an understanding of modern principles of supervision and training, ensuring effective management and development of team members.
A solid grasp of organization and management techniques is necessary for efficient operation and oversight within the transit division.
Knowledge of District policies and Memorandum of Understanding (MOU) provisions is required to ensure compliance and proper enforcement within daily operations.
Familiarity with technology platforms such as Athena, Power School, Microsoft Word, Microsoft Excel, Microsoft PowerPoint, and other applicable video and radio surveillance systems essential for managing information and supporting operational needs with the division.
Understanding and adherence to occupational health and safety rules, as well as safe working practices relevant to this position, are fundamental for maintaining a secure work environment.
Demonstrate excellent interpersonal skills. Multi-task in a fast-paced environment with many priorities and interruptions, and motivate employees to work cooperatively and conscientiously in activities directly involved in contact with the public.
Understand how change and transition management of all operational practices contribute to successfully launching and supporting new and re-designed schools and programs.
Enjoys working with the challenges of shaping new work in a changing environment with relentless attention to detail and accuracy.
Tenacity, resourcefulness, and the ability to interact effectively with people to acquire information and cooperation.
Personal sense of accountability for the success of all Cleveland students.
Sense of urgency for the work of education reform, balanced with sensitivity to good processes so that results are meaningful, and comfortable with the challenges of shaping new work in a startup enterprise.
Knowledge of public-sector budgeting principles, financial controls, and cost accountability practices.
Ability to analyze financial and operational data to support strategic planning and continuous improvement.
Experience collaborating with executive leadership, finance teams, and external stakeholders to align operational performance with fiscal goals.
Demonstrated ability to communicate complex operational and financial information clearly to leadership and stakeholders.

Minimum Qualifications

Education and /or Experience:

Bachelor’s degree required in Public Administration, Business Administration, Education Administration, Transportation, or a related field. Master's degree preferred
4-7 years of related experience in leading school or organizational design and development.
Excellent organizational skills and ability to balance multiple priorities.
Demonstrate the ability to effectively lead diverse groups of internal and external stakeholders to develop, implement, and monitor benchmarks targeting long-range goals.
Demonstrate strategic and visionary skills with sound technical and analytical ability

Required License:

Must have or obtain within 9 months an Ohio Commercial Class B driver's license with air brakes and passenger endorsements. A satisfactory driving record is required: no DUIs or reckless driving in the past 7 years, no more than two moving violations in the past 3 years, and regular operation of District vehicles.

Physical Requirement:

A 24-hour on-call position that requires the ability to work beyond standard office hours to attend evening and weekend meetings, meet with employees working swing and graveyard shifts, and respond to emergencies.
The employee is frequently required to talk and/or hear feedback as part of various engagement activities.
Local travel may be required for training/meetings.

WORKING CONDITIONS/PHYSICAL DEMANDS

The characteristics listed below are representative of the work environment typically encountered when performing the essential duties of this position. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential duties.

Expected to move, walk, and stand consistently in an office environment and occasionally lift up to 15 pounds
While performing the duties of this job, the employee is regularly required to stand, walk, and sit; use hands to finger, handle, or feel; and reach with hands and arms.
The employee is frequently required to talk and/or hear.
Specific vision abilities required by this job include close vision, color vision, depth perception, and the ability to adjust focus
While performing the duties of this job, the employee is exposed to a normal office environment
Local travel may be required for training/meetings

NOTE: The above-stated duties are intended to outline those functions typically performed by individuals assigned to this classification. This description of duties is not intended to be all-inclusive or to limit the discretionary authority of management to assign other tasks of a similar nature or level of responsibility.

Education

To Apply

Please submit your resume and application using Workday, our online human capital management system. Please note that an offer of employment will be subject to the successful completion of an FBI/BCI background check and drug screen.

EEO Statement

We believe that equity and inclusion at CMSD is an essential call to action, a catalyst to ensure value and appreciation among all our employees, so we may be fair and welcoming now and in the future. CMSD provides equal opportunities for employment, retention and advancement of all personnel by administering all terms and conditions of employment regardless of race, color, ethnicity, ancestry, national origin, sex, disability or genetic information, age, citizenship status, military status, sexual orientation or expression, socio-economic status, title, other dimensions of identity, or any other characteristic protected by law.

The District’s Policy Prohibiting Discrimination, Discriminatory Harassment, and Sexual Harassment and the District’s Title IX grievance procedures, including information on how to report or file a complaint of discrimination, how to report or file a formal complaint of sexual harassment, and how the District will respond, may be accessed on the District’s Civil Rights Notices webpage, available atClevelandMetroSchools.org/domain/105. The District’s Title IX Coordinator / Director of Equal Employment Opportunity may be reached at:

1111 Superior Avenue East, Suite 1800

Cleveland, Ohio 44114

(216)-838-0070

TitleIX_EEO@ClevelandMetroSchools.org

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