TryHackMe is the fastest-growing online cyber security training platform. Our mission is to make learning and teaching cyber security easier by providing gamified security exercises and challenges. Having only been around for a handful of years, we've grown to more than 6 million community members and our growth isn't slowing down! Our Content Engineering team is the engine behind TryHackMe's learning experiences — we build the rooms, paths, and challenges that millions of learners use to develop real-world cyber security skills. We're a team of 30 content engineers, QA engineers, and managers working across blue team, red team, CTF, cloud security, and AI content domains. If you want your work to directly shape how the next generation learns cyber security, this is the team to be on. The Role We're looking for a Senior AI & Automation Engineer to join our Content Engineering team on a 6-month fixed-term contract and accelerate how we build, review, and ship cyber security training content at scale. Our team is already exploring AI-assisted content development, but we need a dedicated engineer to take it from experimentation to production. You'll design and build the AI tooling and automation pipelines that help our content engineers work faster and smarter, from intelligent content generation and review workflows to automated QA and publishing processes. Reporting to the Head of Content Engineering, this role sits at the intersection of AI, automation, and cyber security education. You'll have a direct line to the team producing the content and the autonomy to identify the highest-impact AI and automation opportunities across our workflows. Success in this role looks like: our content engineers spending less time on repetitive tasks and more time on deep technical work, measurable improvements in content throughput and quality, and a set of robust, well-documented AI tools and automations the team can maintain and extend long after the contract ends. We anticipate your responsibilities to include: Designing and building AI-assisted content development tools and pipelines using LLM APIs (OpenAI, Anthropic, etc.) and RAG architectures Developing and optimising prompts and prompt chains for content generation, review, and quality assurance workflows Building and maintaining workflow automations using platforms such as n8n, Make, or Zapier to streamline content creation, review, and publishing processes Integrating AI tooling into existing content development infrastructure, including CI/CD pipelines and cloud environments (AWS/GCP/Azure) Collaborating closely with content engineers, QA engineers, and managers to identify automation opportunities and pain points Evaluating and benchmarking AI model outputs for accuracy, relevance, and educational effectiveness in a cyber security context Creating clear documentation and knowledge-sharing resources so the team can maintain and extend your work Establishing best practices and reusable patterns for AI adoption across content workflows Skills & Requirements Essential 5–7 years of experience in software engineering, AI/ML engineering, or automation engineering Strong proficiency in Python for building tools, integrations, and data pipelines Hands-on experience working with LLM APIs (OpenAI, Anthropic, or similar) in production or near-production environments Experience with prompt engineering techniques including chain-of-thought, few-shot prompting, and evaluation frameworks Practical knowledge of RAG architectures and vector databases Experience building workflow automations using platforms like n8n, Make, or Zapier Familiarity with CI/CD pipelines and cloud platforms (AWS, GCP, or Azure) Ability to work independently, prioritise high-impact work, and communicate clearly with non-AI-specialist teammates Desirable Interest in or experience with cyber security concepts and training Experience working in education technology or content-heavy platforms Familiarity with fine-tuning or evaluating LLMs for domain-specific tasks Start-up or scale-up experience, comfortable with ambiguity and moving fast Experience with Docker and containerised development workflows Benefits & Perks Salary - We hire across 35 countries. We determine salaries based on Geographic Location, Seniority, Interview Performance, and Market Rates using leading compensation benchmarking tools. 100% Remote - In a fully digital world, work from anywhere you want! Tools - a dedicated work laptop any accessories you need to do your best work. Swag Pack - start your TryHackMe journey with a branded swag bundle! Personal Development - £2,500 training budget to acquire certifications, and more. ⛱️ Company Retreat - a n annual company retreat, fully paid for by us! Lunch on us - whether you're a pizza-lover, salad obsessed or a big sushi fan, TryHackMe will cover the cost of your lunch order during our recurring company virtual lunches. Health Insurance - if you're in a country that doesn't have public health care. Enhanced Maternity & Paternity- an enhanced package on top of statutory requirements. 401k / Pension - TryHackMe makes it easy to save money for your retirement.