Penetration Tester (Ethical Hacker) - AI Trainer

DataAnnotation seeks a skilled Penetration Tester to join its AI training initiative as an Ethical Hacker, focusing on evaluating AI-generated security content and solving real-world security problems. This remote, contract role supports flexible scheduling and contributes to shaping how AI systems understand and respond to cybersecurity threats.

The position is remote, listed with a Pennsylvania location context, and offers an hourly rate ranging from USD 50 to 100. Eligible candidates will work on a contractual basis to help train next-generation AI security models.

Location

Remote, Pennsylvania listing

Responsibilities

• Evaluate AI-generated security outputs, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and reliability.
• Develop and solve security-focused technical exercises used to train AI systems.
• Produce clear technical explanations and security-relevant code to support AI training.
• Provide feedback that informs 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; comfortable navigating and patching a codebase.
• Fluency in English with strong writing skills (native or bilingual level).
• Bachelor's degree preferred.
• Cybersecurity certifications are a plus (e.g., 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 times from your own computer at home.
• Competitive pay: projects are paid hourly, up to USD 60 per hour, with opportunities for higher bonus rates on certain projects.
• Impact: help shape the future of AI technologies built for cybersecurity.

Note

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