[Remote] Penetration Testing Engineer - AI Trainer

Note: The job is a remote job and is open to candidates in USA. DataAnnotation is a company focused on developing cutting-edge AI systems, and they are seeking experienced cybersecurity professionals to contribute to AI development. The role involves evaluating AI-generated security content, solving technical security problems, and providing feedback to shape AI security models.

Responsibilities

• Evaluate AI-generated cybersecurity content — including threat analysis, 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 shapes the next generation of AI security models

Skills

• 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 adjacent fields, including government or military cyber operations
• Some coding experience required; comfort navigating and patching a codebase is key
• Fluency in English (native or bilingual level) with strong writing skills
• A bachelor's degree is preferred
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar)

Benefits

• Bonus rates available on some projects
• You'll be able to choose which projects you want to work on and when
• You work on your own schedule, on your own computer, from the comfort of your own home

Company Overview