Remote CTO - AI-Driven Platform Modernization

WinePOS by Innovative Computer Solutions; United States; Remote; USD 250,000 - 450,000; Full time

Benefits offered by this job

Fully remote work across United States

Job summary

Innovative Computer Solutions is seeking a transformative Chief Technology Officer to lead modernization of our beverage software platform and engineering organization. You will set the architecture, drive AI-enabled development, and ensure business continuity while guiding product strategy and technology investments.

Reporting to the President, you will lead a distributed team, balance technical excellence with business outcomes, and partner with executive leadership to deliver a scalable,

Qualifications

• Executive-level accountability for a software organization (CTO/VP Engineering).
• 15+ years of progressive technology experience with 10+ years leading software teams.
• Hands-on modernization of legacy systems in POS/eCommerce contexts.
• Proven ability to build and deploy CI/CD, observability, and automation.
• Experience leading distributed internal, offshore, and external partner teams.
• Oversight of cybersecurity, technology risk, and business continuity.

Responsibilities

• Own technology strategy, software engineering, architecture, and delivery.
• Set product direction and roadmap aligned to commercial priorities.
• Lead platform modernization and migration off legacy platform.
• Establish CI/CD, observability, and automation, with weekly releases.
• Embed AI tooling into development and standardize AI-DLC practices.
• Manage cybersecurity, IT controls, continuity, and risk governance.
• Lead a 14-person distributed engineering organization and mentor leaders.

Skills

CTO experience

Executive leadership

Software dev leadership

Legacy modernization

CI/CD pipelines

Distributed teams

Cybersecurity governance

Business acumen

Tools

CI/CD tooling

Observability tooling

Cloud platforms

Job description

Innovative Computer Solutions is seeking a transformative Chief Technology Officer to lead modernization of our beverage software platform and engineering organization. You will set the architecture, drive AI-enabled development, and ensure business continuity while guiding product strategy and technology investments.

Reporting to the President, you will lead a distributed team, balance technical excellence with business outcomes, and partner with executive leadership to deliver a scalable,