Cybersecurity Director - AI Trainer

DataAnnotation offers a contract based Cybersecurity Director - AI Trainer role that focuses on evaluating AI generated cybersecurity content, designing security focused problems, and delivering feedback to improve AI security models. This is a fully remote position with flexible scheduling and the option to work part time or as a primary focus. Location: McKinney, TX (remote).

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: choose which projects you take on and when you work, on your own computer, from home.
• Competitive pay: projects are paid hourly at $50 to $100 USD per hour, with opportunities for higher bonus rates on select projects.
• Impact: help shape the future of AI technologies built for cybersecurity.

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

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.

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 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).