Executive Director of Transportation Services

Administration and Professionals 2026-01-06 Location:Ridge Road Depot
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.

• 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.

• 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.

• 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

• 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.

• 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.

• 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