Supervisor of Operations

• Location:
  
  Woodbridge School District
  - Administration
• Date Available:
  
  TBD
• Closing Date:
  09/09/2026
• District:
  Woodbridge School District

The Supervisor of Operations is responsible for overseeing and coordinating critical support services that ensure the smooth, safe, and equitable functioning of the school district. This role provides leadership in daily student transportation operations—including routing, scheduling, fleet maintenance, and compliance with all regulatory requirements—while serving as a key liaison for families, staff, and community partners. The Supervisor works closely with departments such as Special Education and McKinney-Vento to provide specialized transportation and ensure access for all eligible students.

In addition to transportation, the Supervisor collaborates with the Building and Grounds Coordinator to maintain clean, safe, and well-functioning school facilities, manage seasonal maintenance tasks, and respond promptly to emergencies. The position also plays a lead role in logistical planning and staffing for summer school programs across the district. Furthermore, the Supervisor oversees district compliance and coordination of services related to McKinney-Vento, homelessness, truancy, and relative caregiver arrangements, ensuring that vulnerable student populations receive the support necessary for consistent school access and success.

• Must hold or be eligible for an educators license in the State of Delaware
• Must hold or be eligible for State of Delaware Certification as a School Principal/Assistant Principal preferred
• Possession of, or eligibility for, Certified School Personnel certification in the State of Delaware preferred
• Minimum four (4) years of administrative/supervisor experience in a school setting preferred
• Minimum of 3–5 years of experience in school operations, transportation management, or facilities oversight preferred
• Experience working with student support services such as Special Education, McKinney-Vento, or Multilingual programs preferred
• Supervisory or leadership experience managing cross-functional teams or departments preferred
• Ability to supervise multiple areas, effectively and efficiently
• Strong organizational, communication, and problem-solving skills, along with a deep commitment to student safety, equity, and operational excellence.
• Ability to handle complex issues, multiple tasks, responsibilities and make decisions quickly and effectively.

• Direct daily student transportation services, including bus routing, driver oversight, scheduling, and fleet maintenance.
• Ensure compliance with all local, state, and federal transportation regulations.
• Coordinate specialized transportation for students with IEPs, those protected under McKinney-Vento, and other qualifying circumstances.
• Serve as the primary point of contact for transportation concerns from families, staff, and community partners.
• Use routing software and student data to design efficient, safe, and cost-effective bus routes; make adjustments based on enrollment changes, road conditions, or student needs.
• Work closely with administration, special education, McKinney-Vento, and other departments to ensure appropriate transportation accommodations for eligible students.
• Attend IEP meetings for individualized student transportation needs.
• Plan, coordinate, and deliver professional development for transportation contractors, bus drivers, and aides to ensure compliance, safety, and service excellence.
• Work closely with building administration for related concerns from parents, staff, and community members and provide support and guidance for investigating incidents and resolving conflicts promptly.
• Support the Building & Grounds Coordinator in organizing preventive maintenance, repairs, and inspections of district vehicles to ensure the fleet remains safe, clean, and consistently road-ready.
• Assist the Lead Constable in developing and implementing emergency transportation procedures,…