Penetration Tester (Ethical Hacker) - AI Trainer

Contract Penetration Tester (Ethical Hacker) - AI Trainer at DataAnnotation, a remote role focused on evaluating AI-generated cybersecurity content and designing security-focused challenges to train AI systems.

Responsibilities

• Assess AI-generated cybersecurity material, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and relevance.
• Develop and solve security-centric technical problems used to train AI systems.
• Draft clear, technically precise explanations and security-relevant code.
• Provide actionable feedback that informs the next generation of AI security models.

Requirements

• Minimum 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 and comfort navigating and patching a codebase.
• Fluency in English with strong writing skills.
• A bachelor’s degree is preferred.
• Cybersecurity certifications are a plus (for example OSCP, CRTO, GREM, GCFA, CEH, or similar).

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: choose projects and hours, using your own computer from home.
• Competitive pay: hourly rate of $50 to $100 USD, with potential bonuses on certain projects.
• Impact: contribute to shaping AI technologies designed for cybersecurity.

Note

• Payments are processed via PayPal.
• This position is available only to candidates located in the US, Canada, UK, Ireland, Australia, and New Zealand.