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- Tasks: Join a talented team to develop an autonomous AI pentester and tackle real-world security challenges.
- Company: Fastest-growing online cyber-security training platform with over 6 million users.
- Benefits: Competitive salary, equity in the venture, and early-stage role with ownership.
- Why this job: Make a real impact in cyber-security while working with cutting-edge AI technology.
- Qualifications: 2+ years of Python experience and a passion for AI and cyber-security.
- Other info: Collaborative environment with opportunities for growth and innovation.
The predicted salary is between 36000 - 60000 ÂŁ per year.
TryHackMe is the fastest‑growing online cyber‑security training platform. In just a handful of years we’ve grown to more than 6 million users and are used by over 1,000 businesses—including governments and Fortune 500 companies like Google and Microsoft. With a $1 M starting budget we’re developing a fully autonomous AI pentester that can plan, exploit, adapt, and report with the speed and precision required for modern offensive security. We’re looking for an engineer to join our small, talented team to test and develop our agent. You must have an interest in cyber‑security, be deeply curious, and passionate about AI agents.
In this role you’ll design the system’s core logic, shape its reasoning, decision paths, memory, and execution flow so it can handle complex offensive tasks reliably. Your day‑to‑day work involves collaborating closely with an offensive security researcher to align the agent with real attacker workflows and improve how it identifies and exploits vulnerabilities.
What you’ll do:
- Contribute to the development and optimisation of our autonomous AI pentesting agent.
- Build and maintain safe environments to run, test, and benchmark agent behaviours.
- Implement core agent capabilities such as reasoning, decision‑making, planning, and tool orchestration.
- Assist in evaluating and comparing large language models (Claude, OpenAI models, Mistral, Llama, etc.) for agent tasks.
- Build UI components and dashboards using React and support browser‑automation workflows with Playwright for agent evaluation.
- Support continuous refinement of the agent through experimentation, observability, and lab testing.
What we’re looking for:
- 2+ years of software development experience with strong Python skills.
- Experience building AI agents (LangChain, CrewAI, Strands SDK, etc.).
- Hands‑on experience with agent design: reasoning, memory, tool orchestration, structured outputs.
- Prompt engineering, RAG, chain‑of‑thought, few‑shot learning, and agent evaluation.
- SQL/NoSQL database and basic data‑modeling knowledge.
- Docker, AWS, cloud deployment, and shell scripting.
- React for frontend/dashboard development.
Bonus points:
- Familiarity with OWASP Top 10.
- Model training and fine‑tuning (LoRA, PEFT) with evaluation experience.
- Cyber‑security expertise: OWASP attacks, pentesting methodologies.
- Experience with TryHackMe or other CTF platforms.
- Playwright for browser automation in agent workflows.
Benefits:
- Competitive salary.
- Equity in the AI pentesting venture.
- Early‑stage role with real ownership and autonomy.
Hiring Process:
You can apply through LinkedIn or by emailing ben@tryhackme.com.
Stage 1: Introductory call with TryHackMe founder and AI agent team (30 min).
Stage 2: Technical exercise and live discussion about your past work building AI agents (1 h).
If you’re applying through email, please answer the following:
- Do you have 2+ years of software development experience with Python?
- Have you built AI agents using frameworks like LangChain, CrewAI, or similar?
- Tell us about your interest in cyber‑security (e.g., experience, CTF platform, passion projects).
- What is your expected salary?
- What exceptional work are you most proud of?
AI Engineer - Pentesting Agent employer: TryHackMe
Contact Detail:
TryHackMe Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land AI Engineer - Pentesting Agent
✨Tip Number 1
Get your networking game on! Connect with folks in the cyber-security and AI space, especially those who work at TryHackMe. Attend meetups, webinars, or online forums to make yourself known and show off your passion for AI agents.
✨Tip Number 2
Showcase your skills through projects! Build a mini AI agent or contribute to open-source projects related to pentesting. This not only demonstrates your expertise but also gives you something tangible to discuss during interviews.
✨Tip Number 3
Prepare for that technical exercise! Brush up on your Python skills and be ready to talk about your past experiences with AI agents. Practise explaining your thought process clearly, as communication is key in tech roles.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets seen by the right people. Plus, it shows you’re genuinely interested in joining our team at TryHackMe.
We think you need these skills to ace AI Engineer - Pentesting Agent
Some tips for your application 🫡
Show Your Passion for Cyber-Security: When you're writing your application, make sure to highlight your interest in cyber-security. Share any relevant experiences or projects you've worked on, especially if they relate to pentesting or AI agents. We love seeing that spark of curiosity!
Tailor Your Application: Don’t just send a generic application! Take the time to tailor your CV and cover letter to match the job description. Mention specific skills like Python, AI agent frameworks, and any experience with tools like Docker or AWS. It shows us you’re serious about the role.
Be Clear and Concise: Keep your application clear and to the point. Use bullet points where possible to make it easy for us to read through your qualifications and experiences. We appreciate a well-structured application that gets straight to the good stuff!
Apply Through Our Website: We encourage you to apply through our website for the best chance of getting noticed. It helps us keep track of applications better and ensures you’re considered for the role. Plus, it’s super easy to do!
How to prepare for a job interview at TryHackMe
✨Know Your Stuff
Make sure you brush up on your Python skills and any frameworks you've used for building AI agents. Be ready to discuss your experience with reasoning, decision-making, and tool orchestration in detail. The more specific examples you can provide, the better!
✨Show Your Cyber-Security Passion
Since this role is all about cyber-security, it’s crucial to demonstrate your interest in the field. Talk about any relevant projects, experiences, or even CTF platforms you've engaged with. This will show that you're not just a techie but also genuinely invested in the security landscape.
✨Prepare for Technical Questions
Expect to dive deep into technical discussions during the interview. Review concepts like prompt engineering, few-shot learning, and agent evaluation. Practising coding problems related to these topics can help you feel more confident when answering technical questions.
✨Ask Insightful Questions
Interviews are a two-way street! Prepare some thoughtful questions about the team, the AI pentesting agent's development, or the company's vision. This shows your enthusiasm for the role and helps you gauge if it's the right fit for you.
