Cybersecurity Technical Writer - AI Trainer

DataAnnotation is expanding its AI security program and seeks a Cybersecurity Technical Writer - AI Trainer to contribute remotely from South Dakota. The role centers on evaluating AI-generated cybersecurity content and designing security-focused problems to train AI security models, with the aim of shaping how AI systems reason about real-world threats.

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 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).

Benefits

• Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
• Flexible schedule: choose projects and when you work, on your own computer, from home.
• Compensation: USD 50 to 100 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.