DataAnnotation

Penetration Tester (AI Training)

DataAnnotation

Remote · Full Time

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Experience
Any
Salary
USD 125 / hour
Openings
1
Posted
1 week ago
Work mode
Work from home
Resume
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Job description

Role Overview

As a Penetration Tester focused on AI training, you will critically assess how AI models simulate offensive security scenarios. Often, models can detail an exploit chain confidently but fail on practical steps such as payload delivery or realistic target conditions. Your task is to identify which attack vectors are legitimate and which are inaccurate or exaggerated by the model.

Key Responsibilities

  • Perform thorough testing of AI offensive reasoning during phases like reconnaissance, exploitation, privilege escalation, and lateral movement to detect inaccuracies and model uncertainties.
  • Identify and dismantle faulty exploit chains featuring filtered payloads, unrealistic prerequisites, or steps that avoid complex actions.
  • Develop and document practical attack paths that are operable in real-world scenarios, highlighting genuine tradecraft techniques.

Suitable Background

This position is ideal for individuals with experience as penetration testers, red team operators, or offensive security engineers.

Qualifications and Expectations

  • Proven hands-on experience in offensive security disciplines such as penetration testing, advanced red-teaming, or competitive capture-the-flag (CTF) events.
  • In-depth understanding of attacker tools and the assembly of authentic exploit chains.
  • Exceptional written communication skills in English to clearly articulate findings and provide effective training feedback.
  • Educational qualifications are not mandatory; emphasis is placed on skills and demonstrable proficiency rather than formal degrees.

Compensation and Work Conditions

Remuneration ranges up to $125 or more per hour, varying according to task complexity and area of specialization. Contributors often earn between $100,000 and $200,000 annually, and some engage in this work as their primary occupation.

About the Company

DataAnnotation supports over one million experts in training premier AI models globally. The platform has disbursed hundreds of millions in payments, averaging contributors remaining active for over five years. It offers flexible, remote work with continuous project availability.

Additional Information

  • Hourly roles with flexible scheduling.
  • Engagement type is independent contractor.
  • Weekly payment cycles.

How they work

Communication Problem Solving Attention to Detail Adaptability

Languages

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