Senior Director of Transportation

Detention Transportation Program Manager

Responsible for the overall management, safety, compliance, and operational performance of a large-scale detention transportation program. This position oversees the transportation of detainees in support of federal detention operations and requires extensive experience managing large transportation fleets, detention transportation operations, and personnel across multiple facilities and geographic areas. The ideal candidate will have direct detention fleet management experience, a strong working knowledge of Detention Transport requirements governing the transportation of detainees, and demonstrated success managing complex, geographically dispersed transportation operations involving buses, vehicles, drivers, dispatchers, maintenance personnel, and support staff.

This is a hands-on operational leadership role in a mission-critical, highly regulated environment.

Key Responsibilities:

• Direct and oversee all aspects of large-scale detention transportation operations, including the movement of detainees between detention facilities, processing centers, airports, courts, medical appointments, and other authorized locations.
• Oversee dispatch and transportation coordination to ensure detainees are transported safely, securely, efficiently, and within established mission timelines.
• Coordinate closely with government agencies.
• Establish and enforce chain-of-custody procedures, manifest documentation, and detainee accountability protocols for every transport movement.
• Develop protocols for special population handling, including detainees with medical or mental health needs, pregnant detainees, individuals requiring disability accommodations, and — where applicable — unaccompanied minors under Flores/TVPRA requirements.
• Oversee restraint policy, restraint equipment management, and associated training and audit programs.
• Establish protocols for emergency response, vehicle breakdowns, accidents, security incidents, medical emergencies, escapes/attempts, and other transportation-related contingencies.
• Manage detainee property handling, grievance documentation, and after-action reporting for transport incidents.
• Manage and maintain a large fleet of detention buses, passenger buses, vans, and support vehicles [target fleet size: 45+ vehicles across 1 operating location, ensuring operational readiness, safety, reliability, and regulatory compliance.
• Develop and implement fleet management policies, procedures, preventive maintenance programs, inspection requirements, and vehicle readiness standards.
• Oversee vehicle security features including cages, restraint anchor points, in-vehicle cameras, GPS/telematics, panic/duress systems, and body-worn camera programs.
• Conduct regular fleet inspections and operational reviews to identify deficiencies and implement corrective actions.
• Manage fleet lifecycle planning, vehicle replacement schedules, and capital equipment requests.
• Ensure all transportation operations comply with applicable government requirements governing the transportation and handling of detainees.
• Maintain and enforce compliance with NDS 2026 (National Detention Standards) for IGSA facilities, and any successor standards issued by gov.
• Ensure full compliance with DOT / Federal Motor Carrier Safety Administration (FMCSA) regulations, including Hours-of-Service (HOS), driver qualification files, vehicle inspection requirements, and 49 CFR Part 382 drug and alcohol testing program requirements.
• Ensure CDL and state DOT compliance across all operating jurisdictions.
• Maintain compliance with Section 1367 confidentiality protections (VAWA/T/U-visa populations) and any TVPRA / Flores Settlement Agreement requirements applicable to in-scope populations.
• Support contract management, government reporting, CPARS submissions, audits, inspections, and formal performance reviews.
• Maintain accurate operational records, fleet documentation, maintenance records, personnel records, incident reports, and compliance documentation in accordance with contract and regulatory requirements.
• Provide leadership and oversight of transportation managers, supervisors, drivers, dispatchers, mechanics,…