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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director of IT- Transportation - **Company:** Ashley Home Stores, Ltd. - **Location:** Tampa, FL, United States - **Experience:** Expert - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Computing Platforms, Architectural Patterns, Cyber Security, Information Systems, Decision Support Systems, Disaster Recovery, IT Management, Machine Learning, Automation of Marketing, Warehouse Management Systems, System Availability, Multi-Agent Systems, Kubernetes, Information Technology - **Published:** June 2, 2026 - **Apply:** https://www.dice.com/job-detail/f722eec5-f34e-4b05-8b65-1bbb21666da6 ## About the Role * Bachelor's degree in information systems, Computer Science, Engineering, or related field (preferred) or equivalent experience, * 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 * Hands-on or strategic experience with AI/ML, automation platforms, and agent-based systems preferred * Knowledge, Skills & Abilities * 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 * Familiarity with agentic development concepts (multi-agent systems, orchestration frameworks, autonomous workflows) * 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 Core Competencies * Strategic Thinking * Innovation & Digital Transformation * Operational Excellence * Leadership & Talent Development * Customer Focus * Data-Driven Decision Making * Additional Expectations * Demonstrate company core values in all responsibilities * Ensure compliance with company policies and procedures * Participate in leadership forums, training, and continuous learning initiatives ## Description * 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. Key Responsibilities Strategic Leadership & Transformation * 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 Operational Excellence * 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 * Application & Platform Management * 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 Program & Project 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 AI, Data & Innovation * 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 Security & Compliance * 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 * Vendor & Technology Management * 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 People Leadership * 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 Business and Product Partnership * 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 * Should add some stuff in here about support. ## Related Videos - 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