Director of Transportation & Fleet Compliance

Position Overview

Reporting to divisional executive leadership, the Director of Transportation & Fleet Compliance owns the organization's entire transportation compliance program — from FMCSA and DOT regulatory adherence to ELD/telematics administration, fleet lifecycle management, safety risk reduction, and budget oversight. This role also serves as the enterprise-level administrator and subject matter expert for the Samsara platform.

Transportation Compliance

• Ensure compliance with all applicable FMCSA, DOT, and state transportation regulations.
• Manage Hours of Service (HOS) compliance, Driver Qualification (DQ) files, Drug & Alcohol Clearinghouse requirements, IFTA reporting, IRP, Unified Carrier Registration (UCR), and vehicle maintenance documentation.
• Lead DOT audits, compliance reviews, and responses to roadside inspections.
• Monitor CSA scores, identify compliance trends, and implement corrective action plans to improve performance.
• Oversee accident review processes and ensure all post-incident regulatory requirements are completed.
• Develop and maintain audit-ready compliance programs that reduce operational and regulatory risk.

ELD & Telematics Management (Samsara)

• Serve as the primary administrator and subject matter expert for the Samsara ELD and telematics platform.
• Conduct routine ELD audits to identify and resolve compliance issues before violations occur.
• Manage HOS compliance, driver logs, Driver Vehicle Inspection Reports (DVIRs), and driver safety scorecards.
• Create dashboards and executive reports using telematics data to monitor fleet performance and compliance metrics.
• Train drivers, dispatchers, and operations leaders on ELD functionality, regulatory requirements, and best practices.

Fleet Operations & Asset Management

• Oversee preventive maintenance programs for fleet vehicles and heavy equipment.
• Develop long-term fleet lifecycle and equipment replacement strategies.
• Track fleet utilization, equipment downtime, maintenance costs, and repair trends to improve operational efficiency.
• Implement initiatives that reduce fuel consumption, maintenance expenses, and overall fleet operating costs.

Safety & Risk Management

• Partner with Safety and Operations teams to reduce vehicle accidents, HOS violations, and roadside inspection issues.
• Utilize telematics data to establish leading safety indicators and performance metrics.
• Implement driver coaching programs focused on speeding, harsh braking, excessive idling, and other high-risk driving behaviors.
• Support insurance audits, claims management, and Experience Modification Rate (EMR) improvement initiatives.

Process Improvement & Compliance Programs

• Develop, update, and maintain transportation compliance policies, standard operating procedures (SOPs), and driver handbook materials.
• Lead continuous improvement initiatives that enhance regulatory compliance, fleet efficiency, and operational performance.
• Prepare executive-level reports highlighting compliance status, fleet KPIs, safety trends, and operational performance.

Budget & Financial Management

• Develop and manage the annual fleet operating budget, including fuel, maintenance, repairs, and capital expenditures.
• Collaborate with Finance and Operations to forecast expenses and identify cost-saving opportunities.
• Lead fleet acquisition, replacement planning, and long-term capital investment strategies.

Leadership

• Lead, mentor, and develop a high-performing transportation compliance and fleet management team.
• Drive organizational change related to transportation systems, regulatory updates, and operational processes.
• Promote a culture centered on safety, accountability, operational excellence, and continuous improvement.

Required Qualifications

• 7–10+ years of progressive leadership experience in transportation compliance, fleet management, or commercial transportation operations.
• Extensive knowledge of FMCSA, DOT, and applicable state transportation regulations.
• Advanced experience administering the Samsara ELD and telematics platform.
• Strong understanding of CSA scoring, Hours of Service regulations, and driver compliance programs.
• Proven success managing DOT audits, compliance reviews, and regulatory inspections.
• Demonstrated ability to implement compliance initiatives and corrective action programs that improve organizational performance.
• Valid driver's license.

Preferred Qualifications

• Bachelor's degree in Transportation, Logistics, Supply Chain, Business Administration, or a related field.
• Certified Director of Safety (CDS) or a comparable transportation safety certification.
• Experience within industrial services, environmental services, construction, or heavy equipment operations.
• Experience developing KPI dashboards and performance reporting using telematics platforms.
• Working knowledge of hazardous materials transportation regulations (49 CFR).