Digital Delivery IT Director – Retail Systems

Overview

Insight Global is seeking a Digital Delivery Director to provide strategic leadership for a cross‑functional team responsible for designing, planning, building, and supporting a global portfolio of websites, applications, and mobile experiences. This leader will evaluate critical issues, define direction, and implement enterprise‑wide practices to ensure all digital initiatives and technical roadmaps align with a multi‑year digital strategy. The Director will drive the vision needed to deliver high‑quality, consistent, and impactful digital experiences for customers around the world.

In addition, the Digital Delivery Director will oversee a delivery team focused on point‑of‑sale (POS) innovation across 5,000 retail stores throughout North America and Latin America. This role is accountable for building modern POS solutions that elevate the customer experience, streamline store operations, and support continued business growth. The Director will lead the architecture, development, and delivery of scalable, high‑performance technology, guiding a team of engineers while partnering closely with product, UX, and business stakeholders to ensure quality, reliability, and consistency across all retail touchpoints.

Salary: $156-$205k

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances.

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• Bachelor’s degree or higher in the Information Technology (IT) field. In lieu of a degree, at least 12 years of experience in IT
• 9+ years of experience in IT
• 5+ years management or enterprise department manager experience including application development.
• Experience with retail business processes, including Point of Sale and Merchandise Management, and related software (e.g. Oracle Retail), applications, integrations, and infrastructure, to support customer sales transactions and store management functions.
• Experience in leading digital delivery teams utilizing Agile software delivery practices, to enable desired business capabilities as defined by business leaders within a Product Management framework.
• Experience in leading application development using MACH architecture (Microservices, API-first, Cloud-native, and Headless), ensuring scalable, flexible, and high-performance solutions with an edge computing architecture.