AI Learning Feedback Specialist

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 handful of years, we've grown to more than 6+ million community members and our growth isn't slowing down! 🥷

The Role

We're looking for an AI Learning Feedback Specialist to help us pioneer something that's never been done before in cyber security education: delivering personalised, AI-powered feedback at scale. You'll be instrumental in building a groundbreaking system that provides our millions of users with customised, tailored feedback on their training exercises, meeting each learner exactly where they are in their journey and coaching them toward mastery.

This role sits at the intersection of AI, education, and cyber security. You'll work with cutting-edge language models to generate, refine, and perfect feedback that genuinely helps our users learn. Your work will directly impact how millions of people worldwide develop practical cyber security skills.

The ideal candidate has extensive experience working with AI tools and prompt engineering, a solid understanding of cyber security fundamentals, and a passion for creating educational content that makes a real difference in people's learning journeys.

Technical Skills & Experience

To be considered for this opportunity, you must have at least 3 years of relevant experience working with AI tools, and a basic understanding of cyber security concepts, tools and frameworks.

You should also demonstrate:

Strong expertise in prompt engineering and prompt refinement, working with several AI tools in an outcome-driven fashion
Agility to pivot, iterate and work with changing priorities easily and seamlessly
A good understanding of cybersecurity concepts, tools and principles including command-line operations, common attack techniques, and security tooling
Familiarity with core OS, networking and web concepts to interpret technical telemetry and learner activities accurately
Quick execution and ability to work in a fast-paced environment, with constant feedback loops and lightning-fast delivery times
Strong verbal and written English communication skills, essential for understanding and replicating great feedback

Job Responsibilities

Generate and refine AI-powered feedback for TryHackMe training rooms, ensuring outputs are accurate, personalised, and genuinely helpful for diverse learners
Quality assurance and iteration (review feedback against learner telemetry data, identify quality issues, and refine prompts until outputs consistently meet A-level standards)
Pattern recognition and analysis (study learner behavioural patterns across exercises to improve feedback relevance, milestone recognition, and coaching effectiveness)
Evaluation design (define success criteria and behavioural classifications for cybersecurity training scenarios across TryHackMe's extensive room catalog)
Documentation and knowledge sharing (create frameworks for quality assessment, document edge cases, and establish scalable processes for feedback generation)
Collaborate with the engineering team to provide insights on feedback system improvements, edge cases, and user experience considerations
Analyse and adapt (understand how users interact with feedback and continuously improve the system based on effectiveness metrics)
Scale preparation (develop processes and quality standards that can serve millions of users while maintaining personalised, high-quality guidance)

Preferred Skills (nice-to-have):

Experience with TryHackMe or similar cybersecurity training platforms
Cybersecurity certifications or formal training
Background in instructional design, learning science, or educational technology
Experience with learning analytics or educational data mining
Technical writing or developer documentation experience
Previous work in EdTech product development or content creation
Familiarity with JSON data structures and regex pattern matching
Experience analysing command-line logs, network traffic, or security telemetry

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!

🕒 Flexi Time - Choose your own hours as long as you have at least 4 hours of overlap with the UK timezone (from 8am - 6pm)

💻 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 - an 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.

Our Hiring Process