Cybersecurity Director - AI Trainer

Join DataAnnotation to train cybersecurity-focused AI chatbots by reviewing AI-generated security outputs and improving model performance.

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
• Produce clear technical explanations and security-relevant code
• Provide feedback that directly informs and improves next-generation AI security models

Requirements

• 2+ years of hands-on cybersecurity experience in roles such as penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent work
• Experience may include government or military cyber operations
• Coding experience required; ability to navigate and patch a codebase is important
• English fluency (native or bilingual) with strong writing skills
• Bachelor’s degree preferred
• Cybersecurity certifications are a plus, such as OSCP, CRTO, GREM, GCFA, CEH, or similar

Benefits

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

Contracting Details

• Contract role, fully remote (Baltimore, MD listed as location)
• Payment via PayPal
• Available only to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand
• DataAnnotation states it will never ask for any money from applicants

Salary: $50 to $100 USD/hour • Experience: 2+ years • Education: bachelor’s preferred