Transportation Operations Manager Jobs in Delaware

Position Type:
Administration/Supervisor
Date Posted:
8/26/2026
Location:
Woodbridge School District- Administration
Date Available:
TBD
Closing Date:
09/09/2026
District:
Woodbridge School District
POSITION: Supervisor of Operations
LOCATION: Woodbridge School District
REPORTS TO: Assistant Superintendent
START DATE: TBD
CLOSING DATE: September 9, 2026
JOB SUMMARY:
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.
QUALIFICATION REQUIREMENTS:

• 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.

ESSENTIAL DUTIES AND RESPONSIBILITIES:

• 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, and help coordinate bus deployment during evacuations, weather-related closures, or crisis situations.
• Partner with principals and district administrators to align transportation services with instructional schedules and district priorities.
• Coordinate regular safety drills, driver training programs, and professional development related to student behavior, customer service, and emergency response.
• Oversees facility use of all buildings and grounds
• Oversee building and grounds maintenance schedules to ensure safe, clean, and well-maintained learning environments.
• Respond promptly to facilities-related issues and emergencies in collaboration with Building and Grounds Coordinator, custodial and maintenance teams.
• Collaborate with the Building and Grounds Coordinator to schedule seasonal maintenance and groundskeeping tasks, including snow removal, landscaping, and field preparation.
• Collaborate with building administrators to plan and support summer school programs, with an emphasis on logistics, transportation, and site readiness. This will also include staffing for summer school for all programs and needs.
• Ensure alignment of facilities and operations to meet summer program needs.
• Oversee McKinney Vento, Homelessness, Truancy and Relative Caregiver and work closely with building and district administrators to provide services to students.
• Attends Board meetings and prepares reports for the Board as the superintendent may request.
• Completes special projects as necessary.
• Other duties as assigned.

Employment is contingent upon successful completion of all required background checks and clearances.
Compensation for the Supervisor of Operations role will be based on the candidate's educational background, professional qualifications, and prior administrative experience, in alignment with district salary guidelines.
Benefit information is available here: https://dhr.delaware.gov/benefits/education/index.shtml
Visit our website for more information: https://www.woodbridgeblueraiders.com/page/human-resources
Interested in Woodbridge School District's Profile of a Leader? Click here: https://canva.link/em71pr69htoie2d
APPLY HERE:
Internal and External Applicants:
Complete an online application on Frontline and submit a letter of interest, updated resumé, and a minimum of three (3) letters of recommendation dated within the last two (2) years. Additional references may be requested during the selection process. All documents may be attached to the online application.
Application Link: https://www.applitrack.com/joindelawareschools/onlineapp/JobPostings/view.asp?FromAdmin=true&AppliTrackJobId=36949
WORKING CONDITIONS AND EXPECTATIONS:
This is a 12-month position based on a full-year administrative contract. The Supervisor of Operations is expected to work a minimum of 7.5 hours per day, consistent with district expectations for administrative staff, with additional time as necessary to effectively fulfill the responsibilities of the position. Duties may extend beyond the traditional workday and include evening and weekend commitments related to district events, meetings, professional development, and student services activities.
The Supervisor of Operations is expected to maintain consistent and reliable attendance, demonstrate strong leadership and professionalism, and effectively manage a broad range of student services and district operations. Responsibilities continue throughout the summer months and include planning and preparation for the upcoming school year, oversight of student services programs and initiatives, staff supervision, compliance activities, and other administrative duties as assigned. Flexibility, collaboration, and responsiveness are essential to meet the evolving needs of students, families, staff, and the district.
ADA ACCOMMODATIONS DISCLOSURE: Under the Americans with Disabilities Act (ADA), the Woodbridge School District is required to provide reasonable accommodations to qualified employees with disabilities, unless doing so would pose an undue hardship. Qualified employees must have the requisite skills, experience, education, and licenses for the job, and must also be able to perform the essential functions of the job, with or without reasonable accommodations. The information contained in this job description is for compliance with the Americans with Disabilities Act (A.D.A.) and is not an exhaustive list of the duties performed for this position. Additional duties are performed by the individuals currently holding this position and additional duties may be assigned.
The Woodbridge School District is an equal opportunity employer and does not discriminate against employees, applicants, visitors, or others, and does not deny access to educational or other services, based on any characteristic prohibited by law.
Inquiries about compliance should be made to the Title IX Coordinator: Kelley Kirkland, Administration Building 16359 Sussex Highway, Bridgeville, DE 19933. Phone (302) 337-7990