AI Learning Feedback Specialist (3 month contract)

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 weve grown to more than 6 million community members and our growth isnt slowing down!

The Role

Were looking for an AI Learning Feedback Specialist to help us pioneer something thats never been done before in cyber security education: delivering personalised AI-powered feedback at scale. Youll 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 is a 3-month fixed-term contract role with the possibility of extensions depending on performance and workload availability.

This role sits at the intersection of AI education and cyber security. Youll 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 peoples 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 TryHackMes 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 - 2500 training budget to acquire certifications and more.

Company Retreat - an annual company retreat fully paid for by us!

Lunch on us - whether youre 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 youre in a country that doesnt 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

• Stage 1: Short introduction call (30 mins)
• Stage 2: Technical Take Home Exercise
• Stage 3: Technical interview (60 mins)
• Stage 4: Final call with a Co-Founder (30 mins)

At this time we are unable to provide sponsorship.