Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation seeks a Penetration Tester (Ethical Hacker) - AI Trainer on a contract basis to help train AI security models, with remote scheduling and a Mississippi base.

Responsibilities

• Assess AI generated cybersecurity content, including threat modeling, vulnerability analysis, and offensive security techniques, for real world accuracy and applicability.
• Design and refine security focused technical challenges used to train AI systems.
• Produce clear, technically precise explanations and security related 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 related fields, including government or military cyber operations.
• Some coding experience is required; 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, including OSCP, CRTO, GREM, GCFA, CEH, or equivalents.

Benefits

• Fully remote work arrangement: experience remote work from the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: select projects and hours, using your own computer from home.
• Competitive pay: hourly rate of USD 50 to 100; some projects may offer higher bonus rates.
• Impact: contribute to shaping AI technologies designed for cybersecurity.