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

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

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

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

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

Cybersecurity Director - AI Trainer

Job Description