Chief Technology Officer

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

📋 Description

• Take charge of the technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery throughout the organization.

• Determine product direction and prioritize the roadmap by aligning technology investments with commercial goals.

• Spearhead the modernization of the legacy platform, encompassing migration strategies and the target architecture.

• Develop CI/CD pipelines, enhance observability, implement automation, and create a roadmap for cloud and hosting modernization.

• Integrate AI tools into development processes, including automated testing, code review, and accelerated iteration cycles.

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

• Capture institutional knowledge through comprehensive documentation and runbooks.

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

• Assess and prioritize commercially viable AI capabilities that are customer-facing.

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

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

• Establish maturity baselines, targets, and timelines for AI-DLC.

• Advocate for AI-enhanced workflows and process optimizations.

• Complete a technology, product, and delivery assessment within the initial 60 days.

• Present the target architecture and a funded modernization roadmap by 120 days.

• Standardize AI-assisted development practices within the first 120 days.

⛳️ Requirements

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

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

• Practical experience in modernizing legacy systems, including proven leadership in modernizing a POS or eCommerce platform and/or migrating from legacy systems.

• Proven ability to build or deploy CI/CD pipelines, observability systems, and automation within resource-constrained environments.

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

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

• Strong technical expertise complemented by business acumen.

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

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

• Preferred: Leadership in cloud modernization projects on AWS, Azure, or Google Cloud.

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

🏝️ Benefits

• Competitive base salary plus revenue sharing.

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

• Comprehensive medical, dental, and vision coverage.

• Retirement savings program.

• 4 weeks of paid time off (PTO).

• Flexible working arrangements.

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

• Annual global corporate leadership training.