Director of Cartage Transportation

Our Mission Critical Domestic team is anchored by TrumpCard, specialists in the transportation of domestic heavyweight shipments in the time-sensitive, high-value and mission-critical arenas. We are committed to providing the highest level of customer service and operational excellence centered around our core values of proactive communication, a sense of urgency with fast and responsive support, flexibility, industry-leading technology. The team is available around-the-clock 24 hours a day, 7 days a week to deliver on your most challenging logistics needs.

JOB DESCRIPTION SUMMARY

The Director of Cartage Transportation is responsible for building, scaling, and optimizing the company’s cartage and private fleet transportation network. This role owns the strategic and operational performance of the fleet including dispatch structure, driver leadership, asset utilization, route optimization, compliance, cost control, and operational KPI development.

The Director will design and implement a scalable fleet operating model that supports company growth while delivering reliable service performance and strong financial contribution. This role partners closely with Operations, Sales, Finance, and Technology teams to ensure fleet operations align with company objectives and customer service commitments.

ESSENTIAL JOB FUNCTIONS

Fleet Strategy & Network Development

• Develop and execute a cartage and private fleet growth strategy aligned with company revenue and service expansion goals.

• Determine optimal fleet size, equipment mix, and geographic deployment to support operational demand and network growth.

• Design scalable operating models that support multi-market fleet expansion.

• Evaluate and recommend strategies regarding private fleet vs. third-party carrier utilization based on cost, service performance, and operational efficiency.

• Support startup and expansion of new transportation operations including terminal locations, driver staffing, and asset deployment.

Fleet Operations & Dispatch Management

• Design and implement an effective dispatch and driver management structure that supports efficient daily operations.

• Establish route planning, load scheduling, and dispatch processes to maximize service reliability and driver productivity.

• Optimize route density, driver utilization, and equipment productivity.

• Implement operational processes that improve service consistency, operational discipline, and fleet scalability.

• Monitor daily operations to ensure strong service execution and timely problem resolution.

Performance Management & Operational KPIs

Develop and manage operational dashboards and performance reporting for the fleet including:

• Revenue per truck per week

• Gross margin per truck

• Cost per stop

• On-time pickup and delivery performance

• Asset utilization rate

• Claims ratio and service quality metrics

• Driver turnover and retention rates

• Driver safety

• Dispatch-to-driver ratio efficiency

• Fuel efficiency and route optimization

• Overtime management and labor productivity

• Use KPI analysis to identify operational improvement opportunities and drive performance accountability across fleet operations.

Financial & Cost Management

• Monitor and optimize the fleet cost structure, including labor, fuel, maintenance, and equipment utilization.

• Analyze margin contribution of private fleet vs. partner carriers to guide operational decision-making.

• Implement processes to monitor and control driver overtime and labor productivity.

• Develop financial models supporting fleet investment decisions and capital allocation.

• Identify and execute cost reduction initiatives while maintaining high levels of service reliability.

Driver Leadership, Safety & Compliance

• Establish strong driver engagement and communication programs that promote accountability and retention.

• Oversee driver recruitment, onboarding, training, and performance management.

• Foster a culture of safety, professionalism, and operational excellence across the fleet.

• Ensure compliance with DOT regulations and all applicable federal, state, and local transportation requirements.

• Monitor safety performance metrics and implement initiatives to reduce accidents, claims, and safety incidents.

Technology, Systems & Continuous Improvement

• Optimize fleet technology platforms including TMS integration, Samsara telematics usage, ELD compliance, and operational reporting tools.

• Implement standardized processes and operating playbooks for dispatch, routing, and fleet management.

• Utilize analytics and telematics data to identify opportunities for route optimization, productivity improvements, and cost savings.

• Partner with technology teams to improve system integration and operational visibility.

Vendor & Stakeholder Management

• Manage relationships with maintenance vendors, equipment suppliers, and transportation service providers.

• Partner with internal stakeholders including Sales, Operations, Finance, and Customer Service teams to ensure fleet operations support company growth and service commitments.

• Support customer initiatives by ensuring consistent and reliable transportation execution.

Decision Authority & Operational Ownership

The Director of Cartage Transportation has operational decision authority over the company’s private fleet and cartage operations and is accountable for service performance, driver engagement, and fleet profitability.

Operational Authority

The Director has authority to:

• Implement dispatch structures, route planning models, and driver scheduling practices.

• Establish and enforce driver performance standards and accountability programs.

• Implement overtime approval processes and labor productivity standards.

• Modify route structures and dispatch workflows to improve efficiency and service performance.

Fleet & Asset Decisions

The Director will:

• Recommend optimal fleet size, equipment mix, and geographic deployment of assets.

• Recommend equipment purchases, leasing strategies, and asset redeployment.

• Develop lifecycle strategies for fleet assets to maximize utilization and operational efficiency.

Carrier & Network Strategy

The Director will develop recommendations for:

• When freight should move using private fleet assets vs. partner carriers.

• Market expansion opportunities supported by fleet operations.

• Strategic partnerships with regional cartage providers when external capacity is required.

Financial Accountability

The Director is accountable for managing fleet performance against key operational metrics including:

• Revenue per truck

• Gross margin per truck

• Cost per stop

• Asset utilization

• Overtime management

• Driver retention

Cross-Functional Collaboration

The Director works closely with:

• Sales to ensure fleet capacity supports customer commitments

• Finance to monitor fleet profitability and capital planning

• Compliance to ensure regulatory adherence

• Technology teams to optimize TMS, telematics, and operational reporting systems

EDUCATION AND QUALIFICATION REQUIREMENTS

• 8–12 years of experience in fleet operations, transportation, or logistics management, preferably within asset-based freight environments.

• Demonstrated experience managing private fleet operations or cartage transportation networks.

• Proven success implementing operational KPIs and performance management systems.

• Strong financial acumen with the ability to analyze fleet profitability, asset utilization, and cost drivers.

• Experience leading dispatch, fleet management, and driver teams in a multi-site or regional environment.

• Strong knowledge of DOT regulations and transportation compliance requirements.

• Experience with transportation technology platforms including TMS, telematics, and ELD systems.

• Strong written and verbal communication skills.

• Builder mindset with the ability to develop scalable operational processes and operational discipline.

COMPENSATION

$175,000-$200,000, annually we consider a variety of factors in determining base compensation including but not limited to, experience, education, certifications, internal equity, market data and geography.

PHYSICAL REQUIREMENTS

The position is in an indoor, office environment, requires the ability to communicate with internal and external customers or vendors verbally and in writing, sit for periods of time, operate typical office equipment which requires seeing and the use of a keyboard.

This job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee. Duties, responsibilities, and activities may change, or new ones may be assigned at any time with or without notice.