Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation is seeking a contract Penetration Tester (Ethical Hacker) - AI Trainer for a fully remote, Vermont-based role. The position focuses on evaluating cybersecurity content to train AI models, solving security challenges, and delivering feedback across flexible schedules.

Responsibilities

• Assess AI-generated cybersecurity content, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and validity.
• Design and solve security-focused technical problems used to train AI systems.
• Produce clear technical explanations and security-relevant code.
• Provide actionable feedback that shapes 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 required; comfort navigating and patching a codebase is essential.
• Fluency in English with strong writing skills (native or bilingual level).
• A bachelor's degree is preferred.
• Cybersecurity certifications are a plus (eg, 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 working hours, using your own computer from home.
• Competitive pay: hourly rate of USD 50 to 100; higher bonus rates may apply for certain projects.
• Impact: contribute to shaping AI technologies designed for cybersecurity.

Note

Payment is processed via PayPal. We will never ask for money from applicants. This job is available to applicants in the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.