Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a remote Penetration Tester (Ethical Hacker) - AI Trainer to help train AI models by evaluating cybersecurity content and solving security problems. This contract role offers flexible scheduling and project-based opportunities, with the chance to work on your own terms from Wyoming (remote). Compensation is USD 50 to 100 per hour.

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: pick the projects you tackle and set your own hours, using your own computer from home.
• Competitive pay: hourly rate of USD 50 to 100, with potential for higher bonus rates on select projects.
• Impact: contribute to shaping the next generation of AI technologies built for cybersecurity.

Responsibilities

• Assess AI-generated cybersecurity content for real world accuracy and validity, including threat analysis, vulnerability assessments, and offensive security techniques.
• Design and solve security-focused technical problems used to train AI systems.
• Write clear technical explanations and security-relevant code.
• Provide feedback that directly informs 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 related 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 preferred.
• Cybersecurity certifications are a plus (eg, OSCP, CRTO, GREM, GCFA, CEH, and similar).