Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a Penetration Tester (Ethical Hacker) - AI Trainer to assist in training AI models by evaluating AI-generated cybersecurity content and solving security challenges. This fully remote role offers a flexible schedule aligned to your availability, the ability to work from your own machine, and the opportunity to influence the next generation of AI-powered cybersecurity tools.

Responsibilities

• Assess AI-generated cybersecurity content, including threat analysis, 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 cybersecurity experience in roles 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 (native or bilingual level).
• Bachelor's degree is preferred.
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: choose projects and hours on your own terms, using your own computer from home.
• Competitive pay: hourly rates range from 50 to 100 USD per hour, with opportunities for higher bonus rates on selected projects.
• Impact: contribute to shaping the future of AI technologies built for cybersecurity.

Note: Payment is made via PayPal. This job is available to applicants in the US, Canada, UK, Ireland, Australia, and New Zealand. We will never ask for money from you.