Chief Technology Officer

About POS-MAX

POS-MAX provides POS systems, merchant processing, delivery integrations, remote support, and software to hundreds of retail merchants.

We currently operate CRE alongside our own applications for inventory synchronization, delivery integrations, reporting, label printing, and store automation. We have two remote developers and are looking for an experienced, hands-on technical leader to assess our current environment and lead its improvement.

Our longer-term goal is to develop more of our own software products. This engagement could grow into an ongoing leadership position as the business and engineering team expand.

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What we need

Our CEO is not a software engineer. We need someone who can independently answer:

• Is our software reliable, secure, and built on a sound foundation?
• What is missing from our architecture, infrastructure, documentation, and development process?
• Are our developers producing good work at a reasonable pace?
• Could another engineer take over without disrupting the business?
• What should we improve now, and what do we need before building our next products?

We need someone who can personally inspect the code and systems, explain their findings clearly, and take responsibility for managing improvements.

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Initial responsibilities

• Review our codebases, databases, integrations, and overall architecture.
• Assess Windows installations, software updates, monitoring, backups, and recovery.
• Review source control, testing, deployments, security, and company ownership of accounts and credentials.
• Understand each developer’s responsibilities, strengths, and support needs.
• Identify missing capabilities, technical risks, and unnecessary complexity.
• Deliver a prioritized assessment and practical 90-day roadmap.

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Ongoing responsibilities

• Manage our remote developers with clear deliverables, deadlines, and acceptance criteria.
• Personally review important code changes and verify completed work.
• Establish practical testing, release, documentation, and handover procedures.
• Report progress, risks, and decisions directly to the CEO in plain English.
• Guide architecture, staffing, and development of future POS-MAX software products.

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Our environment

• Backend: Python, Django, Django REST Framework, Celery, Redis
• Frontend: React and TypeScript
• Databases: SQL Server and PostgreSQL
• Windows applications: Python desktop tools, installers, and printer integrations
• Automation: AutoHotkey and Windows scripts
• Integrations: CRE POS, Deliverect, delivery APIs, webhooks, and store-to-cloud synchronization

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Who we’re looking for

• Substantial senior engineering experience, including directly managing developers.
• Strong, hands-on Python/Django and database architecture skills.
• Experience inheriting, auditing, and improving existing software.
• Practical understanding of Windows-based customer installations and integrations.
• Experience with reliable synchronization, background jobs, APIs, and failure recovery.
• Ability to balance immediate business needs with long-term maintainability.
• Clear communication with a nontechnical business owner.

Retail, POS, payments, hardware integrations, or software deployed across many customer locations would be especially valuable.

This is not an advisory-only CTO role or a general programming assignment. You must be willing and able to open the code, investigate problems, and lead the people doing the work.

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Engagement

We expect to begin with a paid, clearly scoped assessment, followed by part-time technical leadership if there is a mutual fit.

There is potential for a longer-term role with broader responsibility as we develop our own products. The future arrangement will depend on business needs and demonstrated results.

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How to Apply

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