Chief Technology Officer

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Lead the technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery throughout the organization.

• Define product direction and prioritize the roadmap in alignment with commercial objectives.

• Spearhead platform modernization and transition from the legacy system.

• Assess options for rewriting, replatforming, refactoring, and phased modernization, recommending the optimal architecture and delivery approach.

• Implement CI/CD pipelines, enhance observability, automate processes, modernize cloud and hosting, and establish migration controls and rollback strategies.

• Integrate AI tools into the development process, including automated testing, code reviews, and expedited iteration cycles.

• Oversee cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk management.

• Capture institutional knowledge through thorough documentation and runbooks.

• Lead, mentor, and retain a distributed engineering team of 14 professionals.

• Assess and prioritize commercially viable AI capabilities for customer-facing applications.

• Maintain selective engagement with strategic customers, manage major escalations, participate in product advisory discussions, and tackle technically complex opportunities.

• Provide regular updates to the Board and executives regarding modernization efforts, technology investments, strategy, cybersecurity, and risk management.

• Establish AI-DLC maturity baselines, define target timelines, and implement AI-enabled workflows.

• Evaluate and prioritize customer-facing AI opportunities based on commercial value.

• Model disciplined AI-driven decision-making and validate outputs.

• Complete a comprehensive assessment of technology, product, and delivery within 60 days.

• Deliver a targeted architecture and a funded modernization roadmap within 120 days.

• Implement CI/CD and observability infrastructure while ensuring predictable weekly releases.

• Establish AI-assisted development as a standard practice within the first 120 days.

• Mitigate tribal knowledge through thorough documentation, runbooks, and cross-training initiatives.

• Showcase measurable progress in modernization and enhanced resilience within 12 months.

⛳️ Requirements

• Previous experience as a Chief Technology Officer, VP of Engineering, or in a similar executive role within a software organization.

• Over 15 years of progressive technology experience, including a minimum of 10 years leading software development teams.

• Proven hands-on experience in modernizing legacy systems, with a demonstrated history of leading modernization efforts for POS or eCommerce platforms and/or transitioning from legacy systems.

• Successful track record of building or deploying CI/CD pipelines, observability systems, and automation in resource-limited environments.

• Experience managing distributed teams that include internal, offshore, and external partner resources.

• Executive oversight of cybersecurity, technology risk, operational resilience, and business continuity strategies.

• Strong technical knowledge combined with business acumen.

• Preferred: Experience in retail technology, point-of-sale systems, eCommerce, or payment systems.

• Preferred: Background in the beverage-alcohol, grocery, or specialty retail sectors.

• Preferred: Experience leading cloud modernization initiatives on AWS, Azure, or Google Cloud platforms.

• Preferred: Relevant experience in vertical SaaS, fintech, ERP, or other high-availability transaction environments.

🏝️ Benefits

• Competitive base salary along with revenue sharing opportunities.

• Long-term incentive plan: 20% stock option match, subject to applicable plan terms and vesting schedule.

• Comprehensive medical, dental, and vision insurance coverage.

• Retirement savings program.

• 4 weeks of paid time off (PTO).

• Flexible work arrangements.

• Fully remote work options available across the United States and Canada.

• Annual corporate leadership training on a global scale.