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Director of IT- Transportation

Tampa, FL, US • Posted 1 day ago • Updated 9 hours ago

Full Time

On-site

Fitment

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Job Details

Skills

Retail
Brokerage
Team Leadership
Strategic Leadership
IT Strategy
Roadmaps
Decision Support
Scalability
Emerging Technologies
IT Service Management
High Availability
Disaster Recovery
Business Continuity Planning
Lifecycle Management
Enterprise Resource Planning
WMS
Project Delivery
Budget
Product Strategy
Reporting
Routing
Scheduling
Advanced Analytics
Real-time
Cyber Security
IT Security
IT Management
Computer Hardware
Mentorship
Accountability
Workforce Planning
Recruiting
Performance Management
Training And Development
Partnership
Collaboration
Distribution
Supply Chain Management
Business Cases
Information Systems
Computer Science
FOCUS
Team Management
Transportation Management
TMS
Mobile Applications
Machine Learning (ML)
Logistics
System Integration
Artificial Intelligence
Optimization
Predictive Analytics
Orchestration
Workflow
Business Acumen
Communication
Stakeholder Management
Management
Problem Solving
Conflict Resolution
COTS
Strategic Thinking
Innovation
Talent Management
Customer Focus
Decision-making
Regulatory Compliance
Policies and Procedures
Leadership
Training
Professional Development
Life Insurance
Honesty
Continuous Improvement
Operational Excellence
Corporate Social Responsibility

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.

Equal Opportunity Employer

This employer is required to notify all applicants of their rights pursuant to federal employment laws.
For further information, please review the Know Your Rights notice from the Department of Labor.

Employers have access to artificial intelligence language tools (“AI”) that help generate and enhance job descriptions and AI may have been used to create this description. The position description has been reviewed for accuracy and Dice believes it to correctly reflect the job opportunity.

Dice Id: 10409804
Position Id: 64d08f81b562f1e177338104785d98be
Posted 1 day ago

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