Remote Penetration Tester & AI Security Evaluator

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

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.