Supervisor, Transportation

Kamehameha Schools

1d•Onsite

About The Position

Supervises transportation staff, ensuring bus operations and high-value assets meet organizational goals and service requirements. Analyzes operational performance and implements initiatives to improve safety, reliability, on-time performance, and cost effectiveness. Manages DOT-required training and departmental regulatory compliance, and recommends and implements programs to enhance service delivery. Oversees both in-house and contracted bus services, establishes performance expectations, and identifies training or corrective actions to support workforce effectiveness. Ensures adequate operational coverage and collaborates with campus stakeholders to coordinate transportation services that meet KS program needs.

Requirements

High school diploma or equivalent.
Minimum two (2) years supervisory/management experience.
Minimum two (2) years experience in a transportation job related field, to include but not limited to traffic safety and/or traffic management.
Valid Driver’s license.
Ability to understand and implement current or new State or Federal DOT rules that impact KS employees.
Advanced computer knowledge and comfort with business applications.
Positive attitude and willingness to continuously learn new skills and knowledge; ability to demonstrate increasing competence.
Ability to train others in the performance of assigned duties.
Ability to read and comprehend traffic management systems, training materials, and correctly instruct others.
Excellent verbal and written communication skills (including via radio); excellent conflict resolution skills.
Ability to work flexible schedules to accommodate after-hours school-related functions and activities.
Demonstrated values of inclusion, role model for others.
Excellent ability to assess competing priorities, appropriately prioritize and delegate, and manage multiple demands simultaneously.

Nice To Haves

Bachelor’s degree in business, technology, hospitality, or other related field.
Experience working in an organization with various trades.
Knowledge of Human Resources regulations and practices.
CDL license, Type A or Type B with S and P endorsements.

Responsibilities

Supervises daily transportation operations, ensuring efficient, safe, policy-aligned service delivery while addressing operational or personnel issues, making route or assignment adjustments as needed, and maintaining effective engagement and span of control across the team.
Drives continuous improvement by developing and implementing initiatives that strengthen contract performance, cost efficiency, and service quality across all transportation activities.
Supports innovation and service enhancements, contributing to efforts that improve the overall transportation experience for employees, students, and families through technology, digital tools, and other contemporary service solutions.
Provides effective team leadership, setting clear expectations and fostering a high performance culture through coaching, training, and workforce planning to ensure optimal staffing and service levels.
Fosters an inclusive, team-oriented environment by maintaining positive working relationships and encouraging collaborative problem solving across the department.
Builds strong relationships internally and externally, collaborating with stakeholders, vendors, and families to resolve issues and uphold KS values in all interactions.
Leads safety and compliance programs, overseeing records management, conducting inspections, and implementing improvements in response to audit findings.
Ensures full regulatory compliance for KS owned bus operations, maintaining adherence to all applicable health, transportation, environmental, and government standards to protect students and staff.
Oversees and delivers safety, compliance, and technical training, ensuring staff maintain required knowledge and certifications.
Manages accident and incident investigations, completing required reports, analyzing root causes, enforcing corrective actions, and providing performance improvement training aligned with state and federal transportation standards.
Responds to and resolves safety related incidents and complaints, ensuring proper documentation, follow up, and corrective action for concerns from staff, families, and the public.
Conducts regular inspections and work quality reviews to verify performance meets established standards and customer expectations through observations, audits, and stakeholder engagement.
Assesses and coordinates responses to transportation emergencies, ensuring clear communication with internal teams and maintaining student and staff safety during breakdowns, weather events, accidents, and rescue bus operations.
Supports budget development by analyzing ridership, routes, service standards, and staffing needs to ensure resources align with operational and quality expectations.
Identifies and implements tools, materials, and procedures that enhance safety, efficiency, and work quality, including procurement and training for new practices.
Assesses and plans workforce needs, developing schedules and staffing strategies that balance daily operations, special projects, and shifting service priorities.