Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a contract Penetration Tester (Ethical Hacker) to serve as an AI Trainer, focusing on evaluating AI-generated cybersecurity content and solving security problems, with remote work, flexible scheduling, and paid project work via the platform after an assessment.

Responsibilities

• Assess AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for accuracy and real-world relevance.
• Design and solve security-focused technical problems used to train AI systems.
• Produce clear technical explanations and write security-related code.
• Provide actionable feedback that helps shape 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 and comfort navigating and patching a codebase.
• Fluency in English with strong writing skills (native or bilingual).
• A bachelor's degree is preferred.
• Cybersecurity certifications are a plus (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 timings, using your own computer from home.
• Competitive pay: projects paid hourly at $50 to $100 USD; higher bonus rates available for certain projects.
• Impact: help shape the future of AI technologies built for cybersecurity.

Note

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