Director of Information Technology

IT Director / Head of Technology Full-Time | Remote | Monthly Travel to Florence, Italy About Trust the Locals Trust the Locals is an innovative AI-powered travel technology company developing a digital platform that combines artificial intelligence, curated travel data, and local expertise to transform how people discover and experience destinations. Our platform is designed to provide intelligent, personalized, and trustworthy travel discovery, connecting users with carefully selected hotels, restaurants, and authentic experiences. As we continue developing our AI platform, we are seeking an experienced IT Director / Head of Technology to lead its technical evolution, oversee ongoing development, and ensure the platform is secure, scalable, reliable, and prepared for international growth. This is a senior technical leadership position requiring both strategic thinking and hands-on technical expertise. We are not looking for a traditional IT administrator. We are looking for someone capable of understanding an existing software product, working with its current developers, making architectural decisions, and taking responsibility for the platform’s long-term technological development.

Key Responsibilities
Platform Development & Technical Leadership
* Take ownership of the existing platform’s technical development.
* Review and understand the current codebase, software architecture, infrastructure, and development progress.
* Collaborate with existing developers to ensure continuity and a smooth transition of technical responsibilities.
* Define and oversee the platform’s technical roadmap.
* Lead frontend, backend, and AI-related development.
* Evaluate code quality, identify technical risks, and implement improvements.
* Ensure the platform remains stable, reliable, maintainable, and scalable.
* Oversee integrations with third-party APIs and external services.
* Establish software development standards, documentation, testing, and quality assurance processes.
* Contribute directly to technical implementation when necessary. Artificial Intelligence & AI Integration
* Oversee the integration and implementation of AI models and Large Language Models (LLMs).
* Evaluate AI providers, APIs, and technical solutions based on performance, reliability, cost, and security.
* Design and improve intelligent search, recommendation, and personalization systems.
* Develop or oversee Retrieval-Augmented Generation (RAG) architectures where appropriate.
* Manage integrations between AI models and structured platform information.
* Implement processes to improve AI response accuracy, relevance, and consistency.
* Identify and mitigate AI-related risks, including hallucinations, prompt injection, and data leakage.
* Monitor AI performance, response latency, API usage, and operating costs.
* Evaluate emerging AI technologies and their potential applications within the platform. Cybersecurity & Infrastructure Protection
* Develop and maintain a comprehensive cybersecurity strategy.
* Protect the platform’s applications, databases, infrastructure, APIs, and user information.
* Implement secure authentication and authorization systems.
* Establish role-based access controls and least-privilege access policies.
* Ensure secure management of credentials, API keys, secrets, and administrative permissions.
* Implement encryption for data in transit and at rest.
* Coordinate vulnerability assessments, penetration testing, and security reviews.
* Identify and mitigate application vulnerabilities and unauthorized access risks.
* Establish backup, disaster recovery, and incident response procedures.
* Implement security monitoring, logging, and anomaly detection.
* Evaluate the security of third-party services and technology vendors. Data Privacy & Regulatory Compliance
* Work toward compliance with GDPR and other applicable privacy and data protection regulations.
* Implement privacy-by-design and privacy-by-default principles.
* Establish appropriate data retention, deletion, and minimization practices.
* Support consent management and technical processes for data subject requests.
* Evaluate privacy risks associated with AI models and third-party integrations.
* Ensure personal information is handled and stored securely.
* Collaborate with legal and privacy professionals when necessary. Cloud Infrastructure, Databases & Scalability
* Oversee cloud infrastructure and development environments.
* Manage databases, data storage, and information pipelines.
* Design secure processes for importing, validating, and updating platform information.
* Maintain data integrity, availability, and traceability.
* Implement CI/CD pipelines and secure deployment procedures.
* Optimize infrastructure performance and operating costs.
* Establish monitoring, observability, and error-tracking systems.
* Design systems capable of supporting increased user traffic and international expansion.
* Ensure business continuity and technical resilience. Technical Strategy & Team Management
* Collaborate directly with the founders to translate business objectives into technical priorities.
* Define development milestones, timelines, and resource requirements.
* Coordinate internal developers, external contractors, and technology partners.
* Evaluate technical vendors and software solutions.
* Maintain clear documentation of the platform’s architecture and technical processes.
* Oversee secure access to source code, cloud environments, and company-owned technology.
* Identify technical risks and communicate them proactively.
* Provide regular updates on development progress, priorities, and challenges.
* Support future recruitment and development of the technology team.
* Help establish a long-term technology strategy aligned with the company’s growth. Mandatory Requirements
* Significant professional experience in software engineering and web platform development.
* Previous experience in technical leadership roles such as Tech Lead, Head of Engineering, Software Architect, or CTO.
* Strong understanding of frontend and backend architectures.
* Ability to review, understand, maintain, and improve an existing codebase.
* Experience developing and integrating REST APIs and/or GraphQL.
* Strong knowledge of modern backend technologies such as Python, Node.js, TypeScript, Java, or equivalent.
* Experience with relational and/or NoSQL databases.
* Strong knowledge of Git, code review, and version control.
* Experience with cloud platforms such as AWS, Google Cloud, or Microsoft Azure.
* Experience with containerization, deployment, and CI/CD pipelines.
* Strong understanding of cybersecurity fundamentals and secure software development.
* Knowledge of OWASP security principles and common web application vulnerabilities.
* Experience with authentication, authorization, encryption, and secure access management.
* Understanding of GDPR and data protection principles.
* Practical experience integrating AI models or LLM-powered services into software products.
* Ability to make architectural decisions and solve complex technical challenges.
* Experience managing technical teams and coordinating development projects.
* Excellent communication, problem-solving, and organizational skills.
* Fluency in both English and Italian, written and spoken.
* Proficiency in Google Workspace: Drive, Docs, Sheets, Slides, and Calendar.
* Experience using CRM platforms and understanding CRM integrations, APIs, and data flows.
* If not based in Florence, Italy, availability to travel to Florence at least once per month. Preferred Qualifications
* Previous experience as a CTO, Head of Engineering, or Founding Engineer at a technology startup.
* Experience launching AI-powered products, SaaS platforms, or digital marketplaces.
* Advanced knowledge of OpenAI API, Anthropic, Gemini, or comparable AI technologies.
* Experience with RAG, vector databases, embeddings, and semantic search.
* Experience building recommendation engines and personalization systems.
* Knowledge of geolocation systems, mapping services, and geographic APIs.
* Experience with travel platforms, marketplaces, or booking systems.
* Familiarity with OWASP security guidance for LLM applications.
* Experience designing high-availability cloud architectures.
* Knowledge of Infrastructure as Code tools such as Terraform.
* Experience optimizing AI API costs and cloud infrastructure expenses.
* Familiarity with technical due diligence and preparing technology products for investment. Who We’re Looking For We are looking for a technically strong, entrepreneurial, and highly responsible individual who combines strategic vision with practical execution. Someone capable of taking ownership of an evolving AI platform, identifying technical challenges before they become critical, and building secure, scalable solutions. The ideal candidate is comfortable operating in a startup environment, where autonomy, speed, adaptability, and accountability are essential. This role requires someone who understands that rapid development must never come at the expense of security, data protection, code quality, or long-term reliability.

How to Apply
Please submit:
* Updated CV/resume.
* Technical portfolio, GitHub profile, or relevant projects, where available and shareable.
* Brief description of software platforms or technology products developed.
* Specific experience with artificial intelligence and LLM integrations.
* Main programming languages, frameworks, and cloud technologies used.
* Years of professional experience.
* Availability and earliest possible start date. For relevant projects, please describe your specific technical contributions, responsibilities, technologies used, and measurable outcomes. Required Application Question Imagine joining Trust the Locals while an AI-powered platform is already under development by an external technical team. What would be the first five actions you would take during your first 30 days to evaluate the existing codebase, assess security, ensure development continuity, and prepare the platform for international growth?