Cybersecurity Technical Writer - AI Trainer

DataAnnotation is offering a remote, contract role as a Cybersecurity Technical Writer - AI Trainer. You will help train AI models by evaluating AI-generated security content and solving security problems. This fully remote position provides flexible schedules, engaging, project-based work, and the opportunity to influence how AI strengthens cybersecurity. The role is remote with Massachusetts as the base location.

Responsibilities

• Evaluate AI-generated cybersecurity content for real-world accuracy and validity, including threat analysis, vulnerability assessments, and offensive security techniques.
• 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 cybersecurity experience in areas 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 and comfort 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 (eg OSCP, CRTO, GREM, GCFA, CEH, and similar).

Benefits

• Fully remote work from anywhere in the United States, Canada, United Kingdom, Ireland, Australia, and New Zealand.
• Flexible schedule: choose projects and when you work, using your own computer from home.
• Competitive pay: hourly rates range from USD 50 to USD 100, with opportunities for higher bonus rates on select projects.
• Impact: contribute to shaping AI technologies designed for cybersecurity.
• Payment and eligibility: Payments are processed via PayPal. This role is open to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand.