Penetration Tester - AI Trainer

DataAnnotation; Washington (District of Columbia); On-site; USD 69,000 - 138,000; Part time

Benefits offered by this job

Flexible project selection

Work from home

Bonus rates on some projects

Job summary

DataAnnotation is seeking experienced cybersecurity professionals for contract work, with the flexibility to work remotely and set your own schedule. You will evaluate AI-generated security content, solve technical security problems, and provide feedback that directly shapes AI systems.

Some team members work full-time while others focus primarily on this work. Pay starts at $50–$100+ per hour, with potential bonus rates on select projects.

Qualifications

• 2+ years hands-on cybersecurity experience across roles (pen testing, red team, IR, DFIR, threat intel, etc.).
• Some coding experience and ability to patch a codebase.
• Fluent English with strong writing skills.
• Bachelor's degree preferred.
• Cybersecurity certifications (OSCP, CEH, etc.) are a plus.

Responsibilities

• Evaluate AI-generated cybersecurity content 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 shapes future AI security models.

Skills

Cybersecurity experience

English writing

Code navigation

Education

Bachelor's degree preferred

Tools

Python (coding basics)

Job description

About The Job

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and setting your own schedule.

About The Job

We are looking for experienced cybersecurity professionals to help advance AI development. Cybersecurity platforms are increasingly powered by AI — but these systems still need practitioners with real-world experience to validate whether the outputs actually hold up in practice. That's where you come in.

As a member of DataAnnotation's team, you'll work closely with state-of-the-art AI models on tasks like evaluating AI-generated security content, solving technical security problems, and providing feedback that directly shapes how these systems reason about real-world threats and defenses. Some team members fit this work alongside a full-time role, while others treat it as their primary focus.

Advantages Of Contracting With Us

• You'll be able to choose which projects you want to work on and when
• You work on your own schedule, on your own computer, from the comfort of your own home
• Competitive pay: projects are paid hourly starting at $50-$100+/hr, with bonus rates available on some projects

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 shapes the next generation of AI security models.

Qualifications

• 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; comfort navigating and patching a codebase is key.
• Fluency in English (native or bilingual level) with strong writing skills.
• A bachelor's degree is preferred.
• Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note

Payment is made via PayPal. We will never ask for any money from you. This job is only available to those in Argentina, Australia, Brazil, Canada, Denmark, Germany, India, Ireland, the Netherlands, New Zealand, Norway, the Philippines, Poland, Romania, Sweden, Ukraine, the United Kingdom, and the United States. This is an independent contractor position. #cybersecurity