[Hiring] Chief Technology Officer @Wine POS

Role Description

ICS is an established B2B retail software provider at a pivotal moment. The company is investing strategically in technology to fuel growth, improve customer experience, and optimize operations — and that investment requires modernizing a mature, business-critical platform. We are looking for a transformational Chief Technology Officer to own that mandate.

Reporting directly to the President, the CTO will own the engineering vision and strategy, shape the target architecture and modernization path, and lead the continued cultural transformation to AI-driven development (AI-DLC) across the organization. This is a hands-on, player-coach executive role: the CTO sets direction and leads through managers and team leads while remaining close enough to architecture, cloud, security, product, and delivery decisions to challenge assumptions and intervene when required. The primary mandate is to modernize the legacy platform and the engineering organization around it, while protecting business continuity, customer confidence, and future scalability.

The ideal candidate is a balanced transformation leader who combines executive judgment, product orientation, technical credibility, and disciplined execution — someone who raises standards and makes difficult trade-offs while building trust, developing leaders, and guiding the organization through change with clarity, even under uncertainty.

Key Responsibilities

• 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 platform modernization, including migration off the legacy platform, by evaluating rewrite, replatform, refactor, and phased-modernization options and recommending a target architecture and delivery path.
• Establish CI/CD pipelines, observability, and automation to support reliable, predictable weekly releases, and set the cloud and hosting modernization roadmap, including sequencing, migration controls, and rollback readiness.
• Embed AI tooling into the development process (AI-DLC) — automated testing, smarter code review, faster iteration cycles — and make AI-assisted development standard practice across engineering.
• Own cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk governance for a platform serving both trade customers and end consumers.
• Reduce tribal knowledge by getting institutional knowledge out of people’s heads and into documentation and runbooks, making the platform easier to maintain, improve, and ramp new engineers into.
• Lead, develop, and retain a distributed 14-person engineering organization spanning internal, offshore, and external partner resources, setting clear expectations and building a team that ships consistently and owns its work.
• Evaluate and prioritize commercially viable customer-facing AI capabilities on their commercial merit, separate from internal AI-DLC tooling adoption.
• 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.

AI and Operating Expectations

• Make AI-assisted development a standard practice across the engineering organization, embedding AI tooling into automated testing, code review, and iteration cycles.
• Establish the organization’s AI-DLC maturity baseline and a validated target and timeline, and lead the mindset shift required to get there.
• Separately assess and prioritize customer-facing AI opportunities on commercial merit, distinct from internal AI-DLC tooling adoption.
• Model disciplined AI-enabled decision-making for the engineering organization, verifying outputs and exercising sound judgment with technical and customer data.
• Champion new workflows and process improvements that support ICS’s broader AI-enabled operating model and raise team effectiveness.

Qualifications

• 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, not theoretical — 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 that demanded ruthless prioritization and speed.
• 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: able to connect engineering decisions to business outcomes and hold credible conversations with the President about what the work means for the business.

Preferred Qualifications

• Retail technology, point-of-sale, eCommerce, or payments experience.
• Beverage-alcohol, grocery, or specialty retail industry experience.
• Cloud modernization leadership on AWS, Azure or Google Cloud transformation experience.
• Adjacent experience in vertical SaaS, fintech, ERP, or other high-availability transaction environments.

What Success Looks Like

• Completes a technology, product, and delivery assessment within the first 60 days, establishing baselines and aligning leadership on modernization priorities and decision criteria.
• Delivers an agreed target architecture and a funded modernization roadmap by 120 days, with CI/CD and observability infrastructure deployed and the team shipping on a predictable weekly cadence.
• Makes AI-assisted development standard practice, with tooling integrated and adopted by the engineering team within the first 120 days.
• Reduces tribal knowledge through platform documentation, runbooks, and cross-training, while keeping the technical roadmap locked, communicated, and on track.
• Shows measurable modernization progress, stronger delivery predictability, improved product execution, and increased resilience within 12 months.
• Builds trust and credibility with the President, the executive team, and the Board through clear communication, sound judgment, and disciplined execution, even under uncertainty.

Compensation and Benefits

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