Senior Penetration Tester

Gridware; Sydney; On-site; AUD 120,000 - 180,000; Full time

Job summary

Gridware is seeking a highly skilled Senior Penetration Tester to join our Sydney team as a full-time resource. You’ll lead and deliver complex, end-to-end security engagements—from traditional penetration tests to advanced adversary simulations—while mentoring consultants and shaping our methodologies.

You’ll work with stakeholders to drive innovation, present findings clearly to technical and executive audiences, deliver remediation-driven reports, and help expand our service offerings.

Qualifications

• 3–5 years of offensive security consulting experience with proven ability to manage and deliver complex engagements.
• Resilience and adaptability under pressure to deliver outcomes.
• Penetration testing certifications such as CRTO, CRTL, OSCP, CPTS, SANS (GXPN, GWAPT) or CREST CCT are strongly regarded.
• Strong analytical and problem-solving skills with creative security approaches.
• Ability to assess applications and infrastructure from technical and business risk perspectives.
• Experience scripting or developing custom tools to improve testing efficiency.
• Excellent stakeholder engagement and communication skills.
• Ability to draft structured, remediation-driven reports aligned to client risk priorities.
• Passion for offensive security and continuous improvement.
• Eligibility to obtain and hold security clearances.
• Confidence in presenting technical concepts at events or knowledge-sharing sessions.

Responsibilities

• Lead and deliver complex security engagements end-to-end.
• Mentor junior consultants and help shape testing methodologies.
• Present findings clearly to technical and executive stakeholders.
• Deliver high-quality, remediation-focused reports with actionable steps.
• Contribute to proposal writing and development of new services.

Skills

Penetration testing

Offensive security

Cloud security

Report writing

Stakeholder engagement

Job description

Gridware is one of Australia’s leading cybersecurity firms. We help businesses stay ahead of threats with sharp thinking, tailored strategies, and technical excellence. Our work spans major industries and focuses on delivering solutions that are not just compliant but intelligent, scalable, and built to last.

About The Role

We’re seeking a highly skilled Senior Penetration Tester to join Gridware as a full-time resource. You’ll lead and deliver complex, end-to-end security engagements - from traditional penetration tests through to advanced adversary simulations - while playing a critical role in shaping our methodologies, mentoring consultants, and strengthening client relationships.

You’ll work closely with stakeholders, drive innovation within the team, and maintain the standard of excellence Gridware is recognised for across the cybersecurity industry.

What You'll Do

• Red Team operations (C2 infrastructure, payload development and evasion, physical, and human layers) - highly desirable
• Cloud pen testing and security assessments
• Internal and External Network and host penetration testing
• Web and API assessments
• Mobile application assessments
• Wireless assessments
• Scope and define engagements, attend ROE calls, and manage client expectations throughout the lifecycle of an assessment.
• Present technical findings in a clear, risk-aligned way to both technical and executive stakeholders.
• Deliver high-quality, concise reports with actionable remediation tailored to each client.
• Mentor and coach junior consultants, providing technical direction, peer review, and support in developing methodologies.
• Contribute to proposal writing, pre-sales activities, and the development of new service offerings.

What You'll Need

• At least 3-5 years of offensive security consulting experience, with proven ability to manage and deliver complex engagements.
• Demonstrated resilience and adaptability in responding to challenges and setbacks, maintaining focus and delivering outcomes under pressure.
• Penetration testing certifications such as CRTO, CRTL, OSCP, CPTS, SANS (e.g., GXPN, GWAPT), or CREST CCT (Applications or Infrastructure) - strongly regarded but not essential.
• Strong analytical and problem-solving skills, with the ability to think laterally and apply creative approaches to security challenges.
• Ability to assess applications and infrastructure from both technical and business risk perspectives.
• Experience scripting or developing custom tools to innovate and improve testing efficiency.
• Excellent stakeholder engagement and communication skills, with the ability to influence, simplify, and articulate complex security issues for both technical and non-technical audiences.
• Ability to draft structured, remediation-driven reports aligned to client risk priorities.
• Strong passion for offensive security, with a curious and innovative mindset, and a drive for continuous improvement.
• Eligibility to obtain and hold security clearances.
• Confidence in presenting technical concepts at community-driven events, conferences, or internal knowledge-sharing sessions.