Chief Technology Officer

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🔥 3 hours ago

🌐 United States, Canada – Remote

🇺🇸 United States – Remote 🇨🇦 Canada – Remote

⏰ Full Time

🔴 Lead

👨‍💼 Chief Technology Officer (CTO)

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1 - 1 employees

In today's economy, it is imperative in your workforce that you have the right people in the right seat. This will lead to increased employee engagement, higher productivity, greater customer loyalty and soaring profits.

📋 Description

• Own technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery across the organization • Set product direction and roadmap prioritization, aligning technology investment with commercial priorities • Lead modernization of the legacy platform, including migration options and target architecture • Establish CI/CD pipelines, observability, automation, and the cloud and hosting modernization roadmap • Embed AI tooling into development, including automated testing, code review, and faster iteration cycles • Own cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk governance • Document institutional knowledge through documentation and runbooks • Lead, develop, and retain a distributed 14-person engineering organization • Evaluate and prioritize commercially viable customer-facing AI capabilities • Maintain selective involvement in strategic customers, major escalations, product advisory discussions, and technically complex opportunities • Provide periodic Board and executive exposure on modernization, technology investment, strategy, cybersecurity, and risk • Establish AI-DLC maturity baselines, targets, and timelines • Champion AI-enabled workflows and process improvements • Complete technology, product, and delivery assessment within the first 60 days • Deliver target architecture and funded modernization roadmap by 120 days • Make AI-assisted development standard practice within the first 120 days

🎯 Requirements

• Prior Chief Technology Officer, VP of Engineering, or equivalent executive accountability for a software organization • 15+ years of progressive technology experience, including 10+ years leading software development teams • Hands-on experience modernizing legacy systems, including demonstrated leadership of a POS or eCommerce platform modernization and/or a migration off legacy platforms • Track record building or deploying CI/CD pipelines, observability systems, and automation in resource-constrained environments • Experience leading distributed teams across internal, offshore, and external partner resources • Executive oversight of cybersecurity, technology risk, operational resilience, and business continuity • Technical depth paired with business fluency • Preferred: Retail technology, point-of-sale, eCommerce, or payments experience • Preferred: Beverage-alcohol, grocery, or specialty retail industry experience • Preferred: Cloud modernization leadership on AWS, Azure or Google Cloud • Preferred: Adjacent experience in vertical SaaS, fintech, ERP, or other high-availability transaction environments

🏖️ Benefits

• Base salary plus revenue sharing • Long-term incentive: 20% stock option match, subject to the applicable plan terms and vesting schedule • Medical, dental, and vision coverage • Retirement program • 4 weeks PTO • Flexible work arrangements • Fully remote work across the United States and Canada • Annual corporate leadership training (global)

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