IT Director - Modernization

Core Responsibilities

• Formulate and execute a multi-year modernization roadmap, aligning the transition from legacy systems to Azure/Java Spring Boot within the broader scope of organization business goals and initiatives.
• Define the architectural and technical vision for the cloud-native environment, driving the adoption of microservices, modern CI/CD patterns, and data migration strategies.
• Act as a strategic advisor to executive leadership, translating complex technical modernization milestones, risks, and dependencies into business-oriented updates.
• Direct team leaders and contributors to ensure predictable, high-quality delivery of modernized applications.
• Establish standards across the software development lifecycle (SDLC), ensuring robust testing frameworks, automated deployments, and code quality in the new Java ecosystem.
• Mitigate delivery risk by identifying technical debt, data integrity gaps, and legacy dependencies early, ensuring zero disruption to core business operations during cutovers.
• Own the operational stability and performance of transitioned applications and Azure’s cloud environment and develop teammates to recognize and resolve issues.
• Implement robust ITIL-aligned service management practices to handle incident, problem, and change management effectively across hybrid environments.
• Define and monitor strict SLAs for system uptime, application performance, and cloud resource utilization, driving a culture of continuous operational improvement.
• Manage departmental capital and operational budgets.
• Manage vendor relationships and statements of work (SOWs), effectively leveraging onshore, offshore, and third-party system integrators to maximize ROI and delivery velocity.
• Optimize total cost of ownership (TCO) in Azure, driving practices to ensure the new Java Spring Boot applications are architected for cost-efficiency.

Requirements

• Bachelor’s degree in computer science, Information Systems, related technical degree and/or equivalent technical expertise or experience
• 10+ years of proven progressive performance in IT, with strong Development and Solution Delivery foundation
• 5+ years management experience, including business relationship management and vendor/contract management
• Proven track record of transitioning legacy applications to modern cloud-native architectures
• Technical literacy in Microsoft Azure ecosystem and modern services architecture utilizing Jave and Spring Boot
• Demonstrated experience in vendor management and strategic resource planning
• Stakeholder management and communication skills, with the ability to bidirectionally translate technical roadmaps and business value
• Preferrred Modernization Specialization: Specific prior experience overseeing code refactoring, AI development tools (Codex, Claude), services development transitioned from legacy codebase. Advanced framework certifications
• Industry Experience: Grocery and/or retail wholesale professional experience
• Advanced degree. MBA or Master’s Degree in a relevant technical field
• Financial management experience. Budget, invoice management, and project cost tracking

Key Competencies

• Change Leadership. Inspire, guide, and drive organizational and cultural change.
• Manage Ambiguity. Comfort operating in complex, highly critical environments with limited documentation
• Team Development. Build a thoughtful, competent project team that can handle multiple initiatives.
• Optimize Work Processes. Focused on leveraging application modernization to fundamentally improve business processes, efficiency, and system scalability.
• Customer Focus. Preferred Modernization Specialization: Specific prior experience overseeing code refactoring, AI development tools (Codex, Claude), services development transitioned from legacy codebase.