Chief Technology Officer (CTO) Remote (anywhere in United States) + 1 more

The Company is seeking a Chief Technology Officer to lead its technology strategy and modernize a mature, business-critical software platform while maintaining business continuity and customer confidence. The role oversees engineering, architecture, infrastructure, delivery, cybersecurity, and technology risk, and sets product priorities in line with business goals. The CTO will guide platform and cloud modernization, establish reliable release practices through automation and observability, and make AI-assisted development a standard engineering practice. Responsibilities also include developing a distributed engineering team, strengthening documentation and operational resilience, assessing customer-facing AI opportunities, and communicating strategy and progress to executive and board-level stakeholders. Candidates should have prior CTO, VP of Engineering, or equivalent executive experience, at least 15 years in technology, and 10 or more years leading software development teams. Hands-on experience modernizing legacy systems, along with a track record implementing CI/CD, observability, and automation, is required. Applicants should have experience leading distributed teams and overseeing cybersecurity, technology risk, and business continuity. Strong technical depth, business judgment, and the ability to connect engineering decisions to commercial outcomes are essential; experience in retail technology, transaction platforms, or cloud modernization is an advantage.

Hiring Company

Wine POS