AI Training Penetration Tester — Remote, Flexible Hours

DataAnnotation; Australia; Remote; AUD 202,000 - 288,000; Full time

Job summary

DataAnnotation is seeking a hands-on Penetration Tester to evaluate offensive security reasoning and map attack paths a real operator would use. You’ll test recon, exploitation, privilege escalation, and lateral movement while identifying where models bluff.

We value practical skills over formal degrees, with a remote, flexible work setup and project-based engagements across international teams. Strong English writing is essential.

Qualifications

• Hands-on offensive security experience: penetration testing, red-teaming, or CTF at a serious level.
• Fluency with the attacker's toolkit and how real exploit chains come together.
• Clear written English: your explanations are the training signal.
• No degree required. We care about what you can do, not where you learned it.

Responsibilities

• Test offensive reasoning across recon, exploitation, privilege escalation, and lateral movement, and see where the model bluffs.
• Break the exploit chains that don't hold up: filtered payloads, impossible preconditions, and steps that skip the hard part.
• Write the attack path that actually works when the model falls short, with the tradecraft a real operator would use.

Skills

Offensive security

Penetration testing

Red team operations

CTF experience

Clear written English

Job description

DataAnnotation is seeking a hands-on Penetration Tester to evaluate offensive security reasoning and map attack paths a real operator would use. You’ll test recon, exploitation, privilege escalation, and lateral movement while identifying where models bluff.

We value practical skills over formal degrees, with a remote, flexible work setup and project-based engagements across international teams. Strong English writing is essential.