Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation offers a remote contract opportunity for an experienced Penetration Tester (Ethical Hacker) to train AI models by evaluating AI-generated cybersecurity content and solving security problems. This project-based role provides flexible scheduling and the chance to directly influence the development of AI security models from Rhode Island.

Compensation is hourly, in the range of USD 50 to 100 per hour.

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: choose which projects to take on and set your own hours, from your own computer at home.
• Competitive pay: hourly rates with the possibility of higher bonuses on select projects.
• Impact: help shape the future of AI technologies built for cybersecurity.

Responsibilities

• Evaluate 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.
• 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; comfort navigating and patching a codebase is key.
• Fluency in English (native or bilingual) with strong writing skills.
• A bachelor's degree is preferred.
• Cybersecurity certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note

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