Director of IT - Retail AI Applications and DevOps

Job ID: a1qPL0000086R5lYAELocation: Chicago, Illinois, United StatesSalary: $160,000 - $190,000Posted: 2026-08-17Company: Addison GroupTitle: Director of Information Technology - Retail AI Applications and DevOpsLocation: Chicago, IL (Onsite)Salary Range: $160,000 – $190,000 / year + 10-15% BonusBenefits: This role is eligible for medical, dental, vision, 401(k) and PTO. Must be authorized to working in the United States. This position is not eligible for sponsorship. A growing omnichannel retailer is conducting a confidential search for a Director of Information Technology to lead its technology organization and help redefine how AI and technology are used across the business.This is not a traditional IT Director position focused primarily on administration and keeping systems running.We are looking for a builder, operator and business problem solver who can own the technology environment while working directly with business leaders to identify problems and rapidly deliver solutions.The successful candidate will own IT strategy, AI adoption, cybersecurity, infrastructure, business applications, vendor relationships and a lean internal technology team supporting both corporate operations and a multi-location retail environment.What You'll Own:Develop and execute the company's IT and AI roadmapDrive practical adoption of generative AI across business functionsPersonally identify, prototype and deploy AI-enabled workflowsOwn cybersecurity, infrastructure, identity and network operationsSupport technology across corporate and retail locationsOversee Microsoft/Azure, Google Workspace and Cisco Meraki environmentsPartner with business leaders on ERP, e-commerce, POS and other critical applicationsLead technology vendor negotiations and rationalize technology spendDevelop a lean, high-performing IT organizationTranslate technical decisions into clear business outcomesWhat We're Looking For:Retail technology experience is requiredProgressive IT leadership experience within a multi-location environmentStrong preference for candidates who have demonstrated meaningful career progression within an organizationHands-on experience using modern generative AI tools and shipping AI-enabled workflowsStrong cybersecurity, infrastructure and cloud foundationExperience with Cisco Meraki and Microsoft/Azure environmentsExcellent technology vendor management and negotiation experienceExposure to NetSuite, Shopify, retail POS or similar platforms is highly desirableHigh-energy, highly communicative leadership styleBachelor's Degree requiredThis opportunity is particularly compelling for an accomplished IT Manager or Senior Manager who is ready to step into a Director role with broad ownership and direct access to executive leadership.Candidates should be prepared to discuss an AI-enabled workflow they personally shipped as well as a technology vendor negotiation that produced a meaningful business outcome.Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.