Cybersecurity Director - AI Trainer

DataAnnotation is seeking a Contract Cybersecurity Director - AI Trainer to assess AI-generated security content and influence the evolution of AI security models. The position is based in Philadelphia, PA, with fully remote work options and flexible scheduling paid hourly.

Responsibilities

• Assess AI-produced cybersecurity materials, including threat analyses, vulnerability assessments, and offensive security techniques, for real-world accuracy and reliability.
• Develop and resolve security focused technical challenges used to train AI systems.
• Produce clear technical explanations and security oriented code.
• Provide feedback that informs the evolution of AI security models.

Requirements

• 2+ years of hands-on experience in a cybersecurity role, including 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 at native or bilingual level with strong writing skills.

Benefits

• Fully remote work from anywhere in the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.
• Flexible scheduling to select projects and work times using your own computer from home.
• Competitive pay at $50 to $100 USD per hour, with potential higher bonus rates on select projects.
• Impact: contribute to shaping AI technologies used in cybersecurity.