JOB SUMMARY: The Director of Transportation provides strategic and operational leadership for all aspects of OES's student transportation program. The Director is accountable for ensuring that transportation services are safe, reliable, compliant, student-centered, and aligned with the School's standards of operational excellence and exceptional service. This position reports to the Chief Operating Officer.
The Director leads and has direct supervisory responsibility for the School's transportation team, including all bus drivers and the School's transportation mechanic. In partnership with Human Resources, the Director is responsible for building and sustaining a highly qualified transportation workforce through effective recruitment, onboarding, training, development, performance management, and retention.
This position has primary responsibility for establishing and maintaining the systems, procedures, training, supervision, and accountability necessary to safely transport students each day. The Director leads transportation not simply as a daily service function, but as a critical component of the School's duty of care to students and families and as an important service partner to the broader OES community.
The Director develops a culture in which safety is actively managed, operational risks are anticipated, procedures are consistently followed, employees are thoroughly trained, and incidents and near misses result in disciplined learning and continuous improvement. The position requires strong leadership judgment, a high degree of operational rigor, a commitment to exceptional customer service, and the ability to build systems and teams that perform reliably even in complex or rapidly changing circumstances.
KEY RESPONSIBILITIESSafety, Risk Management, & Student Accountability- Serve as the senior operational leader for transportation safety, establishing and updating safety policies, controls, and standard operating procedures.
- Maintain robust student tracking systems for boarding, transit, and handoffs, alongside clear contingency protocols for emergencies, severe weather, and route disruptions.
- Lead root-cause investigations for accidents or near-misses and analyze operational data to identify and mitigate risks proactively.
Operational Leadership- Provide daily oversight for regular bus routes, field trips, athletic events, and special school transportation needs.
- Design and optimize schedules, routes, dispatch practices, and vehicle assignments to ensure timely and reliable service.
- Build contingency plans for staffing shortages, vehicle downtime, traffic delays, and emergency responses.
People Leadership, Recruitment, & Retention- Directly supervise, coach, and evaluate bus drivers and the campus transportation mechanic.
- Partner with Human Resources to execute active recruitment, onboarding, and retention strategies to maintain a reliable staffing pipeline.
- Design and lead initial and recurring training programs-including safety drills and ride-along audits-to ensure consistent team performance.
Fleet Management- Direct the lifecycle management of the school fleet, supervising the mechanic to prioritize preventive maintenance and vehicle readiness.
- Establish diagnostic and tracking systems to monitor vehicle condition and out-of-service status.
- Develop long-range capital plans for fleet replacement and evaluate new transportation technologies (e.g., GPS, safety systems, sustainability upgrades).
Compliance & Operational Governance- Ensure full compliance with federal, state, and local regulations governing student transport, commercial driving, inspections, and licensing.
- Maintain audit-ready systems for tracking driver background checks, medical clearances, licensing renewals, and safety logs.
- Serve as the liaison to regulatory agencies and school leadership regarding transportation compliance and reporting.
Financial & Resource Management- Develop and manage the department's operating and capital budgets in alignment with school priorities.
- Evaluate routing, vendor options, and resource utilization to maximize efficiency without compromising safety or service quality.
- Manage third-party transportation contracts, vendors, and service providers.
School & Family Partnership- Act as the primary, service-oriented point of contact for families and staff regarding transportation routes, schedule changes, and service feedback.
- Proactively communicate operational changes, service disruptions, or incidents to parents and school administration.
- Collaborate with academic, athletic, facilities, and security teams to align transportation schedules with school programs.
RequirementsMINIMUM QUALIFICATIONS:- Experience: Progressive leadership experience in transportation, fleet management, logistics, school operations, or a safety-critical operating environment.
- Leadership: Proven ability to lead, develop, recruit, and retain operational teams.
- Communication: Excellent written and verbal communication skills, demonstrated commitment to exceptional customer service and collaborative partnership, ability to work effectively with students, families, employees, senior leadership, regulators, vendors, and community partners.
- Education: Bachelor's degree required.
- Technical Skills: Proficiency in Google Workspace, MS Office, and video-conferencing tools; ability to adapt to routing/GPS technology.
- Intercultural Competence: Demonstrated commitment to equity, diversity, and inclusion in the workplace.
- Background Check: Ability to pass a comprehensive background check.
PREFERRED QUALIFICATIONS:- Leadership experience in K-12 school transportation or child-centered transportation services.
- Commercial Driver's License (CDL) or willingness to obtain one.
- Experience with fleet maintenance management, routing software, and GPS tracking.
- Relevant industry safety or transportation certifications.
KNOWLEDGE, SKILLS, AND ABILITIES: - Verbal and written communication skills, ability to manage confidential information in compliance with the law and best practice
- Ability to consistently apply principles of equity and inclusion in day to day work and in the broader workplace community
- Organizational skills, ability to work well on teams
PHYSICAL REQUIREMENTS: This is an operational leadership position requiring regular presence during transportation operating hours and availability to respond to significant transportation incidents or emergencies. The Director must be able to spend time in transportation facilities, on School vehicles, and in the field observing operations and employee performance.
The position may occasionally require early mornings, evenings, weekends, or other hours dictated by School transportation needs and significant operational events.
