Senior Director of Transportation (Detention Services) - Senior Level - Urgent Fill

Position Summary

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, safety personnel, and administrative support staff.
• Ensure all drivers and transportation personnel meet applicable training, licensing, certification, background, medical, and qualification requirements — including DOT medical cards, CDL endorsements, and any client-required certifications.
• Develop staffing plans, shift schedules, deployment strategies, and contingency staffing to support fluctuating and mission-essential transportation requirements, including 24/7 operations.
• Own workforce development, succession planning, career pathing, and performance management for the transportation organization.
• Manage labor relations in [union / non-union] environments, including [applicable collective bargaining agreements with union(s), if any].
• Establish and monitor key performance metrics including on-time performance %, vehicle uptime / availability %, preventable incident rate, cost-per-mile, fuel efficiency, staffing fill rates, and contract deliverable compliance.
• Manage transportation-related budgets [target scale: $[XX] million annual operating budget], operating costs, fuel consumption, maintenance expenses, and fleet replacement requirements.
• Identify opportunities to improve fleet utilization, reduce operating costs, increase vehicle availability, and improve overall program performance.
• Develop and maintain business continuity and contingency plans to ensure uninterrupted transportation capability during surge periods, natural disasters, or emergency situations.
• Establish and maintain a culture of safety, security, accountability, compliance, and mission accomplishment.

Required Qualifications

• 10 years of progressive transportation operations experience, with at least 5 years in a director- or senior-manager-level role.
• Minimum 5 years of direct experience in detention, correctional, or law enforcement transportation operations.
• Demonstrated experience managing a large transportation fleet [target: 50 vehicles, of which a substantial portion are passenger buses or vehicles used to transport detainees or incarcerated populations].
• Demonstrated experience leading transportation organizations of [target: 75 personnel] including drivers, dispatchers, supervisors, and fleet support staff.
• Demonstrated experience managing an operating budget of [target: $5M annually].
• Demonstrated experience managing transportation operations across multiple facilities, states, or regions [target: 3 states or regions].
• Extensive knowledge of detention transportation operations, security requirements, and detainee handling procedures.
• Strong working knowledge detention regulations, policies, standards, and procedures governing detainee transportation.
• Experience developing and implementing transportation policies, procedures, staffing models, KPIs, and operational controls.
• Proven ability to manage complex operations under tight deadlines and changing mission requirements.
• Strong knowledge of transportation safety, risk management, incident response, and emergency procedures.
• Bachelor’s degree in Transportation, Logistics, Business Administration, Operations Management, Criminal Justice, Public Administration, or a related field required.
• Equivalent combination of education and directly related experience will be considered (Associate’s degree with 4 additional years of relevant experience, or High School diploma / GED with 8 additional years of relevant experience).
• Excellent leadership, communication, organizational, and problem-solving skills.
• Ability to work effectively with federal government representatives, contracting officers, detention facility leadership, law enforcement, and other external stakeholders.
• Sound judgment under pressure and demonstrated ability to make defensible decisions in high-consequence, time-sensitive environments.
• Strong written communication skills sufficient to produce audit-ready reports and government deliverables.
• Working proficiency with modern fleet, dispatch, and reporting systems is required. Direct experience with the following is strongly preferred:

1. Fleet management platforms (e.g., Fleetio, Samsara, Geotab, Verizon Connect, or equivalent)

2. Telematics and GPS platforms, including in-vehicle camera systems

3. Computer-Aided Dispatch (CAD) systems

4. Computerized Maintenance Management Systems (CMMS)

5. Microsoft Office (Excel proficiency required) and data-analysis / BI tools (e.g., Power BI, Tableau)

6. Federal contracting systems and reporting platforms (e.g., CPARS, WAWF/iRAPT, SAM.gov) as applicable

7. Detention-specific systems (e.g., EARM / ENFORCE Alien Removal Module), where applicable to the role

Pay: $145,000.00 - $185,000.00 per year

Benefits:

• Health insurance

Work Location: On the road

Salary : $145,000 - $185,000