Penetration Tester | Part-time Contract (Sydney or Remote)

Are you a Pen Tester, looking for a side hustle?

An opportunity to take on extra work alongside what you’re already doing, and help shape the future of penetration testing. You’ll be the human behind the machine, validating and guiding AI-driven assessments that are redefining how security testing is done!

About Company

We’re working with a company that is redefining how penetration testing is done - combining AI automation with human expertise to deliver faster, smarter, and more reliable security testing. The platform simulates real-world attacker behaviour, automating repetitive tasks while expert testers validate and refine results for accuracy and actionable insight.

Backed by leading venture investors, we’re building the next generation of AI-driven offensive security tools - empowering organisations to continuously test and strengthen their defences with speed, scale, and confidence.

The Role

We’re looking for a Penetration Tester (3-6 years experience) to join as a contractor and become our human in the loop - the critical expert who keeps the machine honest.

In this role, you will:

• Validate and refine AI-generated test results - identify false positives, correct hallucinated findings, and ensure accuracy before reports go to clients.
• Perform hands-on testing across web apps, APIs, and authentication layers - you’ll have full autonomy to test and explore as you would in a real engagement.
• Collaborate with our AI engineering team - provide feedback on model behaviour, help improve the LLM’s accuracy, and close gaps between human and machine understanding.
• Contribute to high-quality pen testing reports - bringing consulting polish and precision to every client deliverable.
• Grow with us - start on a flexible contract basis, with the potential to move into a more permanent or product-oriented role as we scale.

What we’re looking for

• 3-6 years of experience in penetration testing (web app, black box, API).
• OSCP certification (or similar industry certifications such as CREST or GPEN).
• Strong consulting and communication skills - you can translate findings into actionable insights.
• Pragmatic, collaborative, and curious about AI, automation, and innovation in offensive security.
• Familiarity with industry frameworks (OWASP, ISO, SOC2, etc.).
• Ideally based in Sydney, though remote work is fully supported.

Why This Role?

If you’re tired of the same old pen test cycles and want to work on something more creative and impactful, this is your chance.

You’ll have a direct hand in:

• Shaping how AI can augment and accelerate penetration testing.
• Partnering with engineers and security minds to train the next generation of security tools.
• Working flexibly - some weeks 3 days, others 0, depending on active engagements.
• Joining early in a venture that’s already landed its first customers and backed by top-tier investors.

The Future Is Already Here

This isn’t another contract gig - it’s a chance to be part of something new.

A bridge between human skill and AI capability.

A role that lets you keep your hands on the keyboard and your head in the future.

Join them early - or compete with them later.

How to apply: Click apply or submit your CV to [email protected] for a 100% confidential, informal conversation where your privacy will absolutely be respected.

Decipher Bureau and the clients we partner with are committed to creating a diverse environment and are proud to be equal-opportunity employers. All qualified applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.