Chief Technology Officer

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

📋 Description

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

• Define the product direction and prioritize the roadmap, ensuring technology investments align with commercial objectives.

• Spearhead the modernization of the platform and eCommerce, including migration from the legacy system, while recommending the target architecture and delivery approach.

• Create CI/CD pipelines, observability, automation, and cloud and hosting modernization roadmaps, including migration controls and rollback preparedness.

• Integrate AI tools into the development process through automated testing, enhanced code review, and accelerated iteration cycles.

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

• Capture institutional knowledge through documentation and runbooks.

• Lead, develop, and retain a distributed engineering team of 14 individuals, incorporating internal, offshore, and external partner resources.

• Assess and prioritize commercially viable AI capabilities for customer engagement.

• Maintain selective involvement in strategic customer relationships, major escalations, product advisory discussions, and technically complex opportunities.

• Provide periodic updates to the Board and executive team regarding modernization efforts, technology investments, strategy, cybersecurity, and risk management.

• Establish maturity baselines and timelines for AI-DLC and facilitate the adoption of AI-enabled workflows.

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

• Deliver the target architecture and a funded modernization roadmap within 120 days, ensuring CI/CD and observability infrastructure are deployed.

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

• Demonstrate measurable progress in modernization, enhanced delivery predictability, improved product execution, and increased resilience within 12 months.

⛳️ Requirements

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

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

• Proven hands-on experience in modernizing legacy systems, including demonstrated leadership in POS or eCommerce platform modernization and/or migration from legacy platforms.

• A successful track record of building or deploying CI/CD pipelines, observability systems, and automation in resource-limited environments that required strict prioritization and rapid execution.

• Experience in leading distributed teams, including internal, offshore, and external partner resources.

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

• Technical expertise combined with business acumen, able to link engineering decisions to business outcomes and engage in credible discussions with the President regarding business impact.

• Preferred: experience in retail technology, point-of-sale systems, eCommerce, or payments.

• Preferred: industry experience in beverage-alcohol, grocery, or specialty retail.

• Preferred: leadership experience in cloud modernization using AWS, Azure, or Google Cloud.

• Preferred: relevant 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 of PTO.

• Flexible work arrangements.

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

• Annual global corporate leadership training.