Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation seeks a contract Penetration Tester (Ethical Hacker) - AI Trainer to help train AI models by evaluating cybersecurity content, solving security problems, and providing feedback that shapes how AI systems reason about threats and defenses. The role supports remote work with a flexible schedule. Compensation ranges from USD 50 to 100 per hour, payments are processed via PayPal, and the position is open to residents of the US, Canada, UK, Ireland, Australia, and New Zealand.

Responsibilities

• Evaluate AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for 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 directly 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 fields, including government or military cyber operations.
• Some coding experience; comfortable navigating and patching a codebase.
• Fluency in English with strong writing skills.
• Bachelor's degree preferred.
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

• Fully remote work from locations in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule that lets you choose projects and set your own hours, using your own computer from home.
• Competitive pay on an hourly basis, with rates up to 60 USD per hour and potential higher bonus rates on select projects.
• Opportunity to influence the development of AI technologies designed for cybersecurity.