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AI-Native Technical Right Hand to CTO - Development, Operations & Support

Search - AI Chatbot · local_filter_skipped · UID ~022083142778526483672

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Job Details

Budget $? - $?/hr
ExperienceExpert
DurationUnknown
Weekly hoursMore than 30 hrs/week
Client countryAbout the client
Proposals5 to 10
Interviewing0
Invites sent0
First seenFri, Jul 31, 2026 1:56 PM
Last seenSat, Aug 1, 2026 12:49 AM

Description

Summary I am looking for a long-term technical right hand who can help me operate, support and develop several growing businesses and software platforms. I currently serve as CTO across multiple companies while also handling consulting projects, infrastructure, technical support and day-to-day development. Another company is now being added to the portfolio, and I need someone who can gradually take ownership of a significant part of the technical workload. This is not intended to be a short-term freelance assignment. I am looking for someone who can become deeply involved in the businesses, understand the systems and eventually handle many technical decisions and responsibilities without depending on me for every step. AI is a core part of the role We are early adopters of AI and use it extensively across development, operations, support, internal workflows and customer-facing products. AI is not something we occasionally use to generate text or write a few lines of code. It is deeply integrated into how we work, build products and operate the businesses. You should therefore have a strong practical understanding of the current AI landscape and actively follow how models, tools, agents and development workflows are evolving. I am specifically looking for someone who: * Uses AI extensively in real technical and commercial workflows * Understands the strengths and limitations of different AI models * Has practical experience using AI for development, debugging, research, automation, support or operations * Can design reliable workflows around AI rather than relying on individual prompts * Understands concepts such as context management, tool use, agents, structured outputs, evaluation and human review * Can assess where AI creates genuine commercial value and where it is merely a gimmick * Knows that AI-generated work still requires validation, testing and ownership * Continuously experiments with better ways of working using AI You do not need to know every new model or framework, but you must be genuinely interested in the field, actively use the technology and be able to separate useful developments from hype. Someone who has only used ChatGPT casually will not be a good fit for this role. What you will work on Your responsibilities will gradually include: * Technical support and troubleshooting across several businesses * Monitoring and maintaining production systems * Investigating and resolving bugs, incidents and operational problems * Communicating with users, customers and team members when technical issues arise * Developing and improving internal systems and customer-facing applications * Reviewing existing code and implementing new features * Managing deployments, hosting, integrations and infrastructure * Improving documentation, processes, monitoring and automated testing * Identifying recurring problems and building solutions that prevent them * Designing and improving AI-assisted workflows * Evaluating AI models and tools for specific technical or commercial use cases * Building integrations involving AI models, APIs, agents and automation * Helping the companies use AI to work faster without sacrificing quality or reliability * Helping make the businesses less dependent on me personally The work covers a combination of SaaS platforms, booking systems, internal administration tools, WordPress websites, APIs, integrations and cloud infrastructure. Our current technology landscape includes technologies such as: * C# and .NET * Next.js, React and TypeScript * PostgreSQL and SQL Server * WordPress and PHP * REST APIs and third-party integrations * Vercel, Azure and other cloud services * GitHub and CI/CD pipelines * Large language models and multimodal AI models * AI APIs, coding agents and workflow automation You do not need to be an expert in every technology from the beginning, but you must have strong technical fundamentals and be able to learn unfamiliar systems quickly. The person I am looking for You are likely someone who: * Has professional experience in software development, technical operations or both * Takes ownership instead of waiting for detailed instructions * Can investigate problems independently and communicate clearly * Writes clean, maintainable code * Uses AI as a serious productivity and problem-solving tool * Understands that AI output must be reviewed, tested and challenged * Can turn new technology into practical business improvements * Understands that solving the underlying problem is more important than applying temporary fixes * Is dependable and follows through on commitments * Is honest about progress, mistakes and areas where help is needed * Pays attention to detail and tests work properly before considering it complete * Is comfortable working across several projects and prioritising changing tasks * Wants to build a long-term working relationship rather than complete isolated assignments Integrity, loyalty and reliability are extremely important in this role. You will eventually have access to important systems, customer information and business-critical infrastructure, so I need someone I can trust completely. I value honest work. I do not expect perfection, but I expect transparency, responsibility and a genuine effort to deliver work you can stand behind. Availability and flexibility The role is fully remote. Most work can be planned and completed flexibly, but technical incidents and customer support do not always happen during normal business hours. You must therefore be willing to assist with occasional urgent issues outside the usual schedule, including evenings, weekends or holidays when something business-critical occurs. This does not mean being online every hour of every day. It means taking responsibility and being reasonably reachable when an important system requires attention. Some overlap with European working hours is required. What I offer I can offer: * Stable paid work with the potential to grow into a long-term position * Direct access to several real businesses and production software platforms * A high level of technical and business responsibility over time * Practical experience working at the forefront of applied AI * The opportunity to build AI workflows that create measurable business value * The opportunity to learn how software companies are built and operated * Increasing independence as trust and experience grow * The possibility of taking responsibility for complete systems or business areas * Potential performance-based compensation or profit sharing in the future The ambition is for you to eventually become the person who can keep the technical side of the businesses running when I am unavailable, focused on other projects or taking time away. The amount of responsibility and compensation can grow significantly for the right person. How to apply Please send a concise application covering: * Your professional background and current situation * The most relevant systems or products you have developed or maintained * Your experience with technical support and production incidents * Which of the technologies listed above you have worked with * How you currently use AI in your daily technical work * A specific AI-powered workflow you have built or used repeatedly * An example of how you used AI to create measurable technical or commercial value * An example of a situation where an AI model gave you a poor or incorrect result and how you identified it * An example of a difficult technical problem you investigated and solved * Your normal working hours, time zone and flexibility for urgent incidents * The number of hours you are currently available each week * Why you are interested in becoming a long-term technical right hand rather than working only on individual projects Please include links to relevant GitHub repositories, portfolio projects or other examples of your work where possible. Generic applications that do not address the questions above will not be considered. Applications that only state that you are “passionate about AI” without demonstrating practical experience will also not be considered.

Skills

Artificial Intelligence PHP Amazon Web Services React Native Web Development Product Management +8

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