Remote opportunity at
Jonas SoftwareChief Technology Officer
Innovative Computer Solutions, operating under Jonas Software, is seeking a Chief Technology Officer to guide its engineering operations and platform modernization. For over four decades, the…
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About This Role
Innovative Computer Solutions, operating under Jonas Software, is seeking a Chief Technology Officer to guide its engineering operations and platform modernization. For over four decades, the company has delivered specialized retail technology solutions, including inventory management, point of sale, ecommerce, and payment processing, primarily catering to the wine and liquor retail sector. In this executive capacity, the leader will report directly to the President to oversee architecture, product roadmap prioritization,…
Job Description
Innovative Computer Solutions, operating under Jonas Software, is seeking a Chief Technology Officer to guide its engineering operations and platform modernization. For over four decades, the company has delivered specialized retail technology solutions, including inventory management, point of sale, ecommerce, and payment processing, primarily catering to the wine and liquor retail sector. In this executive capacity, the leader will report directly to the President to oversee architecture, product roadmap prioritization, software engineering, and infrastructure.
This position requires a blend of executive oversight and hands-on guidance. The chosen professional will steer the migration away from legacy systems while maintaining business continuity and customer trust. A core component of the mandate involves driving the adoption of AI-driven development methodologies across the department, alongside managing cybersecurity, technology risk governance, and compliance. The department encompasses a distributed team of fourteen internal, offshore, and external partner personnel.
The ideal candidate possesses deep technical expertise paired with commercial acumen, capable of linking engineering decisions to broader business outcomes. Success in the role includes formulating a comprehensive modernization plan within the initial months, establishing predictable weekly release cycles via automated pipelines, and standardizing AI-assisted workflows. The employer provides a fully remote working arrangement across the United States and Canada, supplemented by benefits including health coverage, retirement offerings, four weeks of paid time off, and revenue sharing.
Responsibilities
- Manage software engineering, infrastructure, DevOps, architecture, and technology delivery.
- Align technology investments and product roadmaps with commercial objectives.
- Formulate and execute a platform modernization strategy away from legacy infrastructure.
- Implement automated testing, CI/CD pipelines, and observability tools for predictable weekly releases.
- Embed AI tooling into standard development processes across the engineering group.
- Oversee technology risk governance, IT general controls, business continuity, disaster recovery, and cybersecurity.
- Produce thorough technical documentation and runbooks to eliminate tribal knowledge.
- Direct a distributed engineering team consisting of fourteen internal, offshore, and external personnel.
- Evaluate customer-facing artificial intelligence features based on commercial viability.
- Engage with strategic clients, executive leadership, and the Board of Directors on risk, strategy, and modernization progress.
Requirements
- Demonstrated executive accountability as a Chief Technology Officer, VP of Engineering, or equivalent in a software enterprise.
- Fifteen or more years of progressive technology experience, featuring at least ten years managing software development teams.
- Practical background in modernizing legacy systems, including leadership of point-of-sale or eCommerce platform migrations.
- Track record of deploying automation, observability, and CI/CD pipelines in constrained environments.
- Experience directing distributed teams across internal, offshore, and external partners.
- Executive-level oversight of operational resilience, technology risk, and cybersecurity.
Qualifications
- Background in retail technology, eCommerce, point-of-sale, or payment systems.
- Familiarity with specialty retail, grocery, or beverage-alcohol industries.
- Cloud modernization expertise involving AWS, Azure, or Google Cloud.
- Adjacent background in vertical SaaS, fintech, enterprise resource planning, or high-availability transaction platforms.
Core Skills
Benefits
- Base salary accompanied by revenue sharing.
- Long-term incentive featuring a 20 percent stock option match subject to vesting schedules.
- Medical, dental, and vision health coverage.
- Retirement program participation.
- Four weeks of paid time off.
- Flexible work arrangements with fully remote access across the United States and Canada.
- Annual corporate leadership training on a global scale.
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this position remote?
Yes, the posting offers fully remote work flexibility across the United States and Canada.
What is the salary for this role?
The source posting does not specify a concrete salary amount, though it mentions a base salary combined with revenue sharing.
How many hours per week is this position?
The scheduled weekly hours are 40.
What level of experience is required?
Candidates must have 15 or more years of progressive technology experience, including at least 10 years leading software development teams and prior executive accountability as a CTO or VP of Engineering.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.