Chief Technology Officer

Role Summary

An established B2B and direct-to-consumer retail software provider is hiring a hands-on Chief Technology Officer. The company's mature point-of-sale and eCommerce platform, built on legacy Java and Swing, is central to how its customers run their businesses. Leadership is committed to modernizing it.Reporting to the President, you'll own technology and product strategy, define the target architecture, and lead the move to AI-driven development across the engineering team. This is a player-coach role. You'll make architecture decisions, manage technical debt deliberately, and build a team that ships predictably. You'll also decide when to maintain what exists and when to rebuild it.Role: Chief Technology OfficerClient: B2B and direct-to-consumer retail software provider

Location: Remote Duration: Full Time PermanentWhat You'll OwnTechnology strategy, architecture, infrastructure, DevOps, and software deliveryProduct direction and roadmap prioritization aligned with commercial goalsPlatform and eCommerce modernization, including migration off legacy Java and Swing, and the cloud roadmapCI/CD, observability, and automation to support reliable weekly releasesAdoption of AI-assisted development (AI-DLC) as standard practice, plus disciplined evaluation of customer-facing AI opportunitiesCybersecurity, IT general controls, compliance, business continuity, and disaster recoveryLeadership of an approximately 14-person distributed engineering organization across internal, offshore, and partner resourcesRegular engagement with the executive team and Board on modernization, investment, and technology riskWhat Success Looks LikeFirst 60 days: A full technology, product, and delivery assessment is complete.

Modernization options are evaluated and leadership is aligned on priorities.By 120 days: The target architecture and a funded roadmap are approved. Release infrastructure is operating on a predictable weekly cadence. AI tooling is adopted across the team, and platform knowledge is documented and shared.By 12 months: Modernization progress is measurable, delivery is more predictable, the platform is more resilient, and there is a clear path to greater AI-DLC maturity.What You BringPrior experience as a CTO, VP of Engineering, or in an equivalent executive technology role15+ years in technology, including 10+ years leading software development teamsHands-on experience modernizing legacy systems, ideally a POS or eCommerce platform, or a migration off Java and SwingA track record of building CI/CD, observability, and automation in lean, resource-constrained environmentsExperience leading distributed teams that include internal, offshore, and external partner resourcesExecutive oversight of cybersecurity, technology risk, and business continuityThe business fluency to connect engineering decisions to growth, margin, and customer impactNice to HaveRetail technology, point-of-sale, eCommerce, or payments experienceExperience in specialty, grocery, or regulated retailAWS cloud modernization leadership (Azure or Google Cloud experience will be considered)Vertical SaaS, fintech, ERP, or other high-availability transaction environmentsInterview Stages:Virtual meeting with PresidentTechnical Round InterviewIdeal Start Date DecemberHow You LeadYou are a steady transformation leader. You make sound decisions with incomplete information and communicate clearly when things are uncertain. You raise standards and address problems directly. You build teams that trust you and take ownership of their work. You're credible in the boardroom and effective at the whiteboard.