Director of IT- Transportation

Ashley Furniture Industries•Tampa, FL

12d

About The Position

The Director of IT – Transportation is responsible for leading the strategic solutioning, execution, and continuous improvement of technology that support transportation operations across the enterprise. This role provides executive-level leadership over transportation systems, infrastructure, and digital transformation initiatives, ensuring alignment with business priorities and long-term organizational goals. The Transportation scope includes Shipper, Brokerage, and Private Fleet. A critical component of this role is close partnership with the Product Organization to define strategy, prioritize work, and ensure value-driven delivery of technology solutions. The Director will collaborate with Product and business leaders to align roadmaps, balance investment decisions, and drive outcomes that maximize business impact. The Director will partner closely with IT leadership, Product Teams and cross-functional business stakeholders to identify, design, and implement scalable, cost-effective technology solutions. This includes driving innovation through AI-enabled transformation, modern architectures, and agentic development frameworks to optimize transportation execution, carrier management, and end-to-end visibility and payment processes. This role is accountable for operational excellence, cybersecurity compliance, team leadership, and the successful delivery of IT programs. The Director also serves as a key decision-maker during critical incidents when senior executives are unavailable.

Requirements

8–12+ years of experience in IT, with significant focus on Transportation Systems
Proven leadership experience managing teams and large-scale IT programs
Experience with Transportation Management Systems (TMS) that support execution for a shipper, a carrier, or a broker, technologies to support the driver in the truck and mobile apps to support the driver and the customer
Demonstrated experience leading digital or AI transformation initiatives
Deep understanding of transportation and logistics processes
Strong expertise in enterprise systems integration and platform architecture
Experience with AI-driven optimization, predictive analytics, and intelligent automation
Strong business acumen and ability to align technology with strategic goals
Exceptional leadership, communication, and stakeholder management skills
Proven ability to manage complex programs in a fast-paced environment
Strong problem-solving and decision-making capabilities
Knowledge of continuous improvement methodologies
Implementation and Support of 3rdparty COTS software

Nice To Haves

Bachelor’s degree in information systems, Computer Science, Engineering, or related field (preferred) or equivalent experience
Hands-on or strategic experience with AI/ML, automation platforms, and agent-based systems preferred
Familiarity with agentic development concepts (multi-agent systems, orchestration frameworks, autonomous workflows)

Responsibilities

Solution and execute the IT strategy for Transportation systems aligned with enterprise and Product Organization strategies and priorities
Partner with Product leadership to co-develop roadmaps, sequencing initiatives based on business value, customer impact, and technical feasibility
Lead AI transformation initiatives, including predictive analytics, intelligent automation, and decision intelligence within transportation operations
Drive adoption of agentic AI systems (autonomous workflows, orchestration agents, and decision-support agents) to improve efficiency and scalability
Identify emerging technologies and industry trends; evaluate and implement solutions that create competitive advantage
Oversee planning, execution, and delivery of IT services ensuring quality, cost efficiency, security, and performance
Establish and enforce IT policies, standards, and best practices across transportation systems
Ensure high availability and reliability of applications, infrastructure, and integrations supporting transportation operations
Lead disaster recovery planning and business continuity efforts
Own the lifecycle management of Transportation Management Systems (TMS), carrier platforms, mobile apps, driver Onboard Computer Systems and other asset tracking and maintenance systems.
Ensure effective integration across enterprise systems (ERP, WMS, planning tools, etc.)
Oversee enhancements, upgrades, and modernization of platforms
Partner with Product and business stakeholders to continuously improve system utilization and value delivery
Accountable for successful delivery of IT programs and projects (scope, budget, timeline, and outcomes)
Work in alignment with Product Organization prioritization frameworks and backlog management processes
Translate complex business challenges into scalable technology solutions
Drive alignment between product strategy and IT execution
Implement standardized reporting and communication processes for stakeholders and executive leadership
Lead initiatives leveraging machine learning, optimization models, and AI agents to enhance routing, carrier selection, cost optimization, and service levels
Develop frameworks for agentic orchestration across transportation workflows (e.g., automated exception handling, dynamic scheduling, autonomous decision-making)
Promote data-driven decision-making through advanced analytics and real-time insights
Ensure strict adherence to cybersecurity policies and regulatory requirements
Lead development and enforcement of IT security processes
Partner with enterprise security teams to mitigate risks and ensure compliance
Evaluate vendor solutions, negotiate contracts, and manage strategic partnerships
Oversee implementation of hardware, software, and third-party platforms
Ensure vendor performance aligns with business expectations
Lead, mentor, and develop a high-performing IT team
Drive a culture of innovation, accountability, and continuous improvement
Manage workforce planning, hiring, performance management, and employee development
Foster collaboration across IT and business teams
Collaborate with Product team, transportation, distribution and supply chain leadership to align IT initiatives with business needs
Support development of business cases and investment strategies
Enable global business functions through scalable IT solutions