Chief Technology Officer (CTO)

The Company is seeking a Chief Technology Officer to lead its technology strategy, engineering, architecture, infrastructure, and delivery. The CTO will modernize a mature, business-critical platform while protecting continuity and customer confidence, set the target architecture and roadmap, and improve release reliability through automation, observability, and cloud modernization. The role also includes making AI-assisted development standard practice, strengthening cybersecurity and operational resilience, documenting institutional knowledge, and leading a distributed engineering organization. The CTO will assess customer-facing AI opportunities, advise on strategic customer and product matters, and communicate technology strategy, investment, and risk to executive and board-level stakeholders. Candidates should have prior CTO, VP of Engineering, or equivalent executive accountability, at least 15 years of progressive technology experience, and 10 or more years leading software development teams. Hands-on experience modernizing legacy systems—including point-of-sale or e-commerce platforms—and establishing CI/CD, observability, and automation is required. Applicants should have experience leading distributed teams and overseeing cybersecurity, technology risk, business continuity, and operational resilience. Strong technical depth, business fluency, and the ability to connect engineering decisions to business outcomes are essential; experience in retail technology, payments, cloud modernization, or other high-availability transaction environments is preferred.