Director of IT – Transportation

Ashley Furniture Industries, Inc. is the largest manufacturer of furniture in the world. Established in 1945, Ashley offers one of the industry’s broadest product assortments to retail partners in 123 countries.

Director of IT – Transportation : Onsite

Locations: Tampa FL, Mesquite TX, Advance NC, Arcadia WI

Position Summary

• 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
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Qualifications

Education

• Bachelor’s degree in information systems, Computer Science, Engineering, or related field (preferred) or equivalent experience

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

Apply today and find your home at Ashley!

Benefits We Offer

• Health, Dental, Vision, Employee Assistance Program
• Paid Vacation, Holidays, and Your Birthday off
• Generous Employee Discount on home furnishings
• Professional Development Opportunities
• Ashley Wellness Centers (location specific) and Medical Tourism
• Telehealth
• 401(k) and Profit Sharing
• Life Insurance

Our Core Values

• Honesty & Integrity
• Passion, Drive, Discipline
• Continuous Improvement/Operational Excellence
• Dirty Fingernail
• Growth Focused

To learn more about Ashley Furniture, our community engagement programs, environmental stewardship, and our core values, please visit our Corporate Social Responsibility information page:

Corporate Social Responsibility

We are an equal opportunity employer and provide a drug-free working environment. While Ashley appreciates the interest of all candidates only those meeting specific position requirements may be contacted. Principals Only.