Remote Penetration Tester for AI Security Training

DataAnnotation; United Kingdom; Remote; GBP 62,000 - 129,000; Full time

Benefits offered by this job

Flexible hours

Remote work

Weekly payouts

Job summary

DataAnnotation is looking for a hands-on Penetration Tester to evaluate offensive reasoning, break flawed exploit chains, and write attack paths a real operator would use. You’ll test recon, exploitation, privilege escalation, and lateral movement, identifying where models bluff and replacing weak steps with solid tradecraft.

Flexible, remote contractor role with high-impact work. No degree required; practical security skills and clear English are valued.

Qualifications

• Hands-on offensive security experience required.
• Fluency with attacker toolkits and how real exploit chains come together.
• Clear written English is essential.

Responsibilities

• Test offensive reasoning across recon, exploitation, privilege escalation, and lateral movement.
• Break exploit chains that don’t hold up: filtered payloads, impossible preconditions, and skipped hard parts.
• Write the attack path that actually works when the model falls short.

Skills

Penetration testing

Red team

CTF participation

Education

No degree required

Job description

DataAnnotation is looking for a hands-on Penetration Tester to evaluate offensive reasoning, break flawed exploit chains, and write attack paths a real operator would use. You’ll test recon, exploitation, privilege escalation, and lateral movement, identifying where models bluff and replacing weak steps with solid tradecraft.

Flexible, remote contractor role with high-impact work. No degree required; practical security skills and clear English are valued.