Chief Technology Officer

Wine POS

2d•Remote

About The Position

Innovative Computer Solutions (ICS), an established B2B retail software provider, is seeking a transformational Chief Technology Officer to lead technology investment, platform modernization, and organizational change. Reporting directly to the President, the CTO owns engineering vision and strategy, target architecture, and the modernization path for a mature, business-critical platform. The role also leads the organization’s transition to AI-driven development as a standard operating model. This is a hands-on, player-coach executive position. The CTO sets direction and leads through managers and team leads while remaining close to architecture, cloud, security, product, and delivery decisions. The central mandate is to modernize both the legacy platform and the engineering organization while protecting business continuity, customer confidence, and future scalability. The CTO is expected to combine executive judgment, product orientation, technical credibility, and disciplined execution while building trust and developing leaders. ICS serves the retail beverage alcohol industry with point-of-sale, inventory, purchasing, ecommerce, reporting, and integrated payments solutions. The position leads a distributed 14-person engineering organization comprising internal, offshore, and external partner resources, and maintains selective involvement with strategic customers, major escalations, product advisory discussions, and complex technical opportunities. The role also provides periodic updates to the Board and executive team on modernization, technology investment, strategy, cybersecurity, and risk. The position is fully remote across the United States and Canada, with scheduled weekly hours of 40. Compensation includes base salary plus revenue sharing and a long-term incentive of a 20% stock option match, subject to plan terms and vesting. Benefits include medical, dental, and vision coverage, a retirement program, four weeks of paid time off, flexible work arrangements, and annual global corporate leadership training.

Requirements

Prior experience as a Chief Technology Officer, VP of Engineering, or equivalent with executive accountability for a software organization.
15 or more years of progressive technology experience.
10 or more years leading software development teams.
Hands-on experience modernizing legacy systems, including demonstrated leadership of a POS or eCommerce platform modernization and/or migration off legacy platforms.
Track record building or deploying CI/CD pipelines, observability systems, and automation in resource-constrained environments requiring 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 and business fluency, including the ability to connect engineering decisions to business outcomes and discuss their business implications credibly with the President.

Nice To Haves

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

Responsibilities

Own technology strategy, software engineering, architecture, infrastructure, DevOps, and delivery across the organization.
Set product direction and roadmap priorities, aligning technology investment with commercial priorities.
Lead platform modernization and migration away from the legacy platform; evaluate rewrite, replatform, refactor, and phased-modernization options and recommend a target architecture and delivery path.
Establish CI/CD pipelines, observability, and automation to support reliable, predictable weekly releases.
Set the cloud and hosting modernization roadmap, including sequencing, migration controls, and rollback readiness.
Make AI-assisted development standard practice across engineering, integrating AI tooling into automated testing, code review, and development iteration cycles.
Establish an AI-driven development maturity baseline, validated target, and timeline, and lead the organizational mindset shift required to achieve them.
Own cybersecurity, IT general controls, compliance, business continuity, disaster recovery, and technology risk governance.
Document institutional knowledge in platform documentation and runbooks to reduce reliance on tribal knowledge and improve maintainability and onboarding.
Lead, develop, and retain a distributed 14-person engineering organization spanning internal, offshore, and external partner resources.
Assess and prioritize customer-facing AI opportunities based on commercial merit, separately from internal AI-development tooling adoption.
Model disciplined AI-enabled decision-making, verifying outputs and applying sound judgment with technical and customer data.
Champion workflows and process improvements that support the broader AI-enabled operating model and improve team effectiveness.
Maintain selective involvement in strategic customers, major escalations, product advisory discussions, and technically complex opportunities.
Provide periodic Board and executive updates on modernization, technology investment, strategy, cybersecurity, and risk.
Complete a technology, product, and delivery assessment within the first 60 days and align leadership on modernization priorities and decision criteria.
Deliver an agreed target architecture and funded modernization roadmap by 120 days, with CI/CD and observability infrastructure deployed and predictable weekly releases underway.
Integrate and drive engineering-team adoption of AI-assisted development within the first 120 days.
Reduce tribal knowledge through documentation, runbooks, and cross-training, while keeping the technical roadmap communicated and on track.
Demonstrate measurable modernization progress, stronger delivery predictability, improved product execution, and increased resilience within 12 months.

Benefits

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