Delivery-Focused Penetration Tester

Cliffside Cybersecurity; Sydney; On-site; AUD 110,000 - 150,000; Full time

Benefits offered by this job

Mentoring program with students

Australian university placement ties

Free mentoring programme

Job summary

Cliffside Cybersecurity in Sydney seeks a mid-level penetration tester taking ownership of engagements from scoping to remediation validation. You will test web apps, APIs, infrastructure, cloud and identity, and review security configurations across AWS, Azure, and Microsoft 365.

Independence and clear reasoning are essential as you contribute to a growing AI-security practice. Exposure to AI-enabled systems is highly desirable, and you will collaborate with senior consultants while mentoring

Qualifications

• Strong penetration testing capability across web, API, cloud and infrastructure.
• Ability to design attack scenarios with realistic threat chaining.
• Experience delivering end-to-end engagements from scoping to remediation validation.
• Clear, evidence-based reporting with practical recommendations.

Responsibilities

• Plan and execute penetration tests across web apps, APIs, infrastructure, cloud and identity.
• Design credible attack scenarios and chain weaknesses across systems.
• Test authentication, authorization and session management by hand.
• Validate controls such as WAFs, rate limiting and MFA.
• Write evidence-based reports and present findings to engineers and CISOs.
• Retest and confirm fixes are effective.

Skills

Web app pentest

API pentest

Infrastructure pentest

Cloud security

Identity testing

Scripting: Python

Scripting: PowerShell

Scripting: Bash

Adversary simulation

Burp Suite

Nmap

Metasploit

BloodHound

Education

Cybersecurity degree or related

Practical certifications (OSCP/OSWE/OSWA/OSEP/CREST)

Tools

AWS

Azure

Microsoft 365

Job description

Cliffside Cybersecurity in Sydney seeks a mid-level penetration tester taking ownership of engagements from scoping to remediation validation. You will test web apps, APIs, infrastructure, cloud and identity, and review security configurations across AWS, Azure, and Microsoft 365.

Independence and clear reasoning are essential as you contribute to a growing AI-security practice. Exposure to AI-enabled systems is highly desirable, and you will collaborate with senior consultants while mentoring