DataAnnotation is looking for a Penetration Tester (Ethical Hacker) - AI Trainer to support the evaluation and training of AI models focused on cybersecurity. This fully remote role involves reviewing AI-generated security content and working through technical security challenges while contributing feedback that improves model quality.

Role Overview

In this position, you will assess cybersecurity material produced by AI, including whether it is accurate and valid in real-world contexts. You will also solve security-focused technical problems that are used to train AI systems, along with writing explanations and code that reflect correct security reasoning.

Responsibilities

Evaluate AI-generated cybersecurity content, including threat analysis, vulnerability assessments, and offensive security techniques, with an emphasis on real-world accuracy and validity.
Design and solve security-focused technical problems used to train AI systems.
Write clear technical explanations and security-relevant code.
Provide feedback that informs and shapes the next generation of AI security models.

Requirements

2+ years of hands-on experience in a cybersecurity role such as penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent work, including government or military cyber operations.
Coding experience required, with comfort navigating and patching a codebase.
Fluency in English (native or bilingual level) and strong writing skills.
A bachelor's degree is preferred.
Certifications are a plus, for example OSCP, CRTO, GREM, GCFA, CEH, and similar.

Compensation and Work Details

Location: Idaho (remote).
Pay: projects are paid hourly at $50 to $100 USD per hour, with opportunities for higher bonus rates on certain projects.
Schedule: flexible scheduling, including selecting projects and determining when you work.
Equipment: work is performed on your own computer.

Benefits

Fully remote: available to work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
Flexible schedule: choose which projects you take on and when you work.
Competitive hourly compensation: $50 to $100 USD per hour, with possible higher bonus rates for certain projects.
Impact: contribute to improving AI technologies built for cybersecurity.
Payment method: payment is made via PayPal.

Contracting Advantages

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
Flexible schedule: choose which projects to take on and when to work, from your own computer.
Competitive pay: hourly projects at $50 to $100 USD, with potential higher bonus rates for select projects.
Impact: help shape the future of AI technologies built for cybersecurity.

Additional Notes

Payment is made via PayPal.
They will never ask for any money from you.
This role is only available to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand.

Penetration Tester (Ethical Hacker) - AI Trainer

Job Description