DataAnnotation is seeking an existing Penetration Tester (Ethical Hacker) to support the training of AI models for cybersecurity use cases. This contract role focuses on reviewing AI-generated security content, creating security-focused technical challenges, and supplying feedback that helps shape next-generation AI security models.

Role Overview

In this position, you will assess whether AI-produced cybersecurity outputs are accurate and valid for real-world scenarios. You will also contribute by designing and solving technical security problems and by providing clear, security-relevant explanations and code that can be used to improve AI model behavior.

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.
Write clear technical explanations and security-relevant code.
Provide feedback that directly contributes to the development of 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, including comfort navigating and patching a codebase.
Fluency in English (native or bilingual level) with strong writing skills.
Bachelor’s degree preferred.
Cybersecurity certifications are a plus, for example OSCP, CRTO, GREM, GCFA, CEH, or similar.

Compensation and Contract Details

Job type: contract
Location: Maine (remote)
Pay: projects are paid hourly at $50 to $100 USD per hour
Higher bonus rates may be available for certain projects

Benefits

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
Flexible schedule: select projects and work times, using your own computer.
Competitive pay: hourly rates of $50 to $100 USD per hour.
Impact: support the development of AI technologies for cybersecurity use cases.

Additional Notes

Payment is made via PayPal.
We will never ask for any money from you.
This role is available only to candidates in the US, Canada, UK, Ireland, Australia, and New Zealand.

Penetration Tester (Ethical Hacker) - AI Trainer