Transportation Director Jobs in Delaware (NOW HIRING)

Transportation Specialist - Charter Services & Dispatch

Terms of Employment:  Full-time, 10-month
Reports to: Transportation Supervisor
Salary:  Current Odyssey Charter School Salary Schedule
About Us:
The future is brighter than ever for Odyssey Charter School, and we are in search of highly motivated, equally passionate individuals to join our team. Odyssey is a full-scale K-12 Charter School currently serving 2,500+ students. Our school features a growing dual immersion program, an innovative Green Initiative, a community food program, and strong academic outcomes.

Odyssey is united in its mission to prepare lifelong learners who are culturally aware, global citizens who utilize critical thinking and problem-solving skills grounded in the classical teachings of Greek education and language. Through the Socratic Method and inquiry-based learning, students are empowered to leverage their unique skills and talents in an equitable and collaborative environment where all students can succeed.

Position Summary

Odyssey Charter School is seeking a highly organized, service-oriented Transportation Specialist to support charter services and daily transportation operations. This position focuses on developing charter business, coordinating contracts and bookings, and providing responsive dispatch support.

The ideal candidate is proactive, detail-oriented, and skilled at building client relationships, managing multiple priorities, and ensuring transportation services are coordinated safely, accurately, and efficiently.

Minimum Qualifications

• High school diploma or equivalent required; associate degree or relevant coursework preferred.
• At least two years of experience in transportation, dispatch, logistics, customer service, sales, school operations, or a related field.
• Strong organizational, communication, customer-service, and problem-solving skills.
• Ability to remain calm, exercise sound judgment, and respond effectively to changing operational needs.
• Proficiency with Microsoft Office, Google Workspace, and electronic recordkeeping systems; experience with routing or dispatch software preferred.
• Valid driver's license and reliable transportation required; school bus CDL and applicable endorsements preferred.
• Ability to meet all required background, child protection, and pre-employment screening requirements.
• Availability to support early-morning, afternoon, and occasional after-hours transportation needs.
• Commitment to collaboration, global citizenship, and working effectively within a multicultural and multilingual school community.

Key Responsibilities

Charter Services and Client Development

• Develop charter opportunities, respond to inquiries, and maintain timely follow-up with prospective and existing clients.
• Build strong client relationships that support bookings, repeat business, and revenue growth.
• Coordinate charter contracts and service details from initial inquiry through completion.

• Partner with the marketing team to promote charter services and identify new opportunities.

Scheduling and Dispatch Support

• Develop and maintain transportation schedules, including charter, athletic, and extracurricular runs.
• Communicate schedule changes promptly to drivers, staff, clients, and other stakeholders.
• Maintain driver call logs, incident reports, sign-ups, and other dispatch documentation.
• Respond to transportation needs, prioritize urgent matters, and escalate concerns appropriately.
• Design and update routes in accordance with OCS procedures and operational needs.
• Administration and Reporting
• Prepare accurate invoices and maintain monthly charter activity and revenue reports.
• Maintain organized transportation records, spreadsheets, databases, and client information.
• Collect and review customer feedback to improve service quality and client retention.
• Provide timely updates and performance reports to transportation leadership.
• Operational Coordination
• Collaborate with the Fleet Specialist to coordinate vehicle maintenance and service needs.
• Support compliance with applicable transportation and safety requirements.
• Maintain productive relationships with school departments to meet transportation needs.
• Provide occasional operational support outside regular business hours.
• Complete additional transportation-related duties as assigned.

Standard Requirements

• Favorable Criminal Background Check
• Favorable Child Abuse Registry Check
• Tuberculin Test
• Mandatory Direct Deposit of paycheck 

Application Procedures

Internal Candidates:
Qualified applicants must complete an online application or submit a current resume with license/certification information. Letters of recommendation are optional.

External Candidates:
Qualified applicants must complete an online application and submit:

• Letter of interest
• Current resume
• Recent evaluations and/or student teaching evaluations
• Transcripts
• Current, Active License/Certification
• Three (3) professional references, must be supervisory level
• Three (3) letters of recommendation dated within the last year 

Previous submissions will not automatically be considered. Applicants must apply specifically for the Job ID associated with this position.

For assistance with the application process or to request a paper application, please contact the OCS Human Resources Team at 302-516-8000.

Equal Opportunity Employer Statement

Odyssey Charter School is an equal opportunity employer. We do not discriminate in employment or educational programs, services, or activities on the basis of race, color, national origin, religion, gender, gender identity, sexual orientation, age, military/veteran status, disability, marital status, or any other protected status in accordance with applicable state and federal laws, including Title VII of the Civil Rights Act of 1964, the Delaware Discrimination in Employment Act, the Americans with Disabilities Act (ADA), and other relevant laws.