Manager of Transportation Supervision

Manager of Transportation Supervision

Department: Pupil Transportation

Reports To: Director of Transportation

Employment Status: Full-Time / Exempt

Grade: 121

Starting Date: Immediately

The Manager of Transportation Supervision is a critical leadership role focused on the frontline workforce. This position is responsible for the safety, performance, and professional development of the entire driving and monitoring staff. By leading a tiered supervisory team, you ensure that every bus route is executed safely, on time, and in compliance with state and federal regulations. This role provides oversight for 2 Transportation Supervisors (Direct Reports), 5 Assistant Supervisors (Indirect Reports), and the total workforce of all Bus Drivers and Bus Monitors.

• Workforce Leadership: Direct and mentor two Supervisors and five Assistant Supervisors, ensuring consistent application of district policies.
• Performance Management: Establish clear KPIs for drivers and monitors regarding on‑time performance, student management, and safety protocols.
• Disciplinary Oversight: Lead the grievance and disciplinary process for the driving staff, conducting investigations and recommending personnel actions.
• Employee Handbook: Lead the annual review, revision, and updating of the Department of Pupil Transportation Employee Handbook in coordination with the Director of Transportation.
• Regulatory Compliance: Collaborate with the Safety & Training team to ensure all drivers and monitors maintain valid CDLs, endorsements, medical certificates, and state certifications.
• Field Inspections: Conduct regular road checks and site visits to audit driver performance and adherence to pre‑trip & post‑trip inspection and other requirements.
• Emergency Response: Serve as the primary escalation point for significant field incidents, including accidents, breakdowns, or security issues.
• Route Advocacy: Collaborate with the routing team to ensure routes are realistic and provide feedback on road conditions.
• Labor Relations: Address morale issues and ensure a positive, professional workplace for frontline staff.
• Recruitment & Retention: Partner with the Safety & Training team to ensure recruitment efforts, interview panels, and orientation while developing retention initiatives.

• Bachelor’s degree in Management, Logistics, Education, or a related field (extensive fleet leadership experience may be substituted).
• Minimum of 5–7 years of experience in transportation or fleet operations.
• At least 3 years in a mid‑to‑senior level management role overseeing a large, diverse workforce.
• Experience in a unionized environment or public sector setting is highly preferred.
• Possession of a valid Virginia Driver’s License with no restrictions or negative points/demerits.
• Possession of (or ability to obtain) a Commercial Driver’s License (CDL) Class B with P and S endorsements is preferred.

• People Leadership: The ability to inspire, hold accountable, and develop a large team of diverse employees.
• Conflict Resolution: Skill in de‑escalating tense situations with staff, parents, or the community.
• Operational Judgment: Making high‑stakes decisions quickly during emergencies or inclement weather.
• Empathy & Integrity: Understanding the rigors of the driving profession while maintaining district standards.

Work requires frequent standing, light lifting up to 25 pounds, sitting, walking, vocal communication for expressing or exchanging ideas, hearing to perceive information at a normal spoken word level and visual acuity for preparing and analyzing written or computer data.

• Requires significant time in the field, including early mornings (pre‑dawn) and late afternoons.
• Exposure to various weather conditions and the industrial environment of a bus depot.
• Must be able to respond to emergencies outside of standard business hours.

EOE.