DataAnnotation is seeking a remote Penetration Tester with a focus on ethical hacking to support AI model training. The role centers on evaluating AI-generated cybersecurity content and solving security problems to help advance AI safety and capability.

Role Summary

This position involves contributing as a remote penetration tester to train AI models by assessing the realism and accuracy of cybersecurity content produced by AI systems and by crafting security-focused challenges used in training. The assignment offers flexible scheduling and remote participation tied to project availability.

Engagement Details

Location: Remote role based in Hawaii
Contract Type: Contract
Compensation: USD 50 to 100 per hour
Experience Minimum: 2+ years in cybersecurity roles

Responsibilities

Assess AI-generated cybersecurity content for real-world accuracy and validity, covering threat analysis, vulnerability assessments, and offensive security techniques
Design and resolve technical security problems used to train AI systems
Produce clear technical explanations and security-relevant code
Provide actionable feedback that informs the next generation of AI security models

Requirements

2+ years of hands-on experience in cybersecurity roles 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 with the ability to navigate and patch a codebase
Fluent in English with strong writing skills
A bachelor’s degree is preferred
Cybersecurity certifications are a plus (examples include OSCP, CRTO, GREM, GCFA, CEH, and similar)

Benefits

Fully remote work from the US, Canada, UK, Ireland, Australia, and New Zealand
Flexible schedule to select projects and work on your own computer from home
Competitive hourly pay with potential higher bonuses on select projects
Opportunity to influence AI technologies designed for cybersecurity applications

Note

Payment is made via PayPal. We will never ask for money from applicants. This role is available to candidates in the United States, Canada, the United Kingdom, Ireland, Australia, and New Zealand.

Penetration Tester (Ethical Hacker) - AI Trainer