Senior Penetration Tester
Summary
Senior penetration tester at a small Sydney cybersecurity consultancy: you'd be the primary delivery person leading pentest engagements end to end (web, API, network, cloud, Active Directory), manage the company's own IT infrastructure, mentor junior testers, and help build the team and processes. Core tech: offensive security tooling, M365/Entra ID, AWS/Azure/GCP.
Salary: $138,000 per year
Ready to stop being one tester in a big machine and become the go-to technical person in a growing consultancy? We're looking for a senior level penetration tester to lead our testing delivery, look after our IT infrastructure, and help grow our team from the ground up.
This isn't a role where you inherit a playbook. You'll write it.
About us
Vanguard Cyber is a Sydney based cybersecurity consultancy dedicated to making a change.
We're small, independent and growing. We believe good security work should be thorough, honest and explained in plain language, and that the people doing it should be supported to keep learning. We invest in graduates, give back to the community, and want our next leader to share that same mindset.
About the role
As a senior level penetration tester, you'll be the primary delivery person for our penetration testing engagements and the technical backbone of the business.
You'll split your time between hands-on testing, leading client engagements end to end, looking after Vanguard Cyber's own IT infrastructure, and helping build the people and processes that let the team scale without losing quality. You'll work directly with the founder and have a genuine say in where the business goes next.
What you'll do
Lead delivery: Own penetration testing engagements from scoping and kick-off through to reporting and debrief, across web, API, internal and external network, cloud and Active Directory
Stay hands-on: Be an active tester on engagements and the person the team turns to when they're stuck
Look after our IT infrastructure: Manage, maintain and secure our internal environment, including Microsoft 365, endpoints, networking, cloud tenancies and our testing infrastructure, so it reflects the standard we recommend to clients
Grow the team: Help shape new roles, take part in hiring, and support the team as it grows from one to a well-rounded practice
Mentor and develop: Coach our graduate and junior testers, review their work, and help them build towards their certifications
Set the standard: Contribute to testing methodologies, report templates, QA processes and internal tooling that keep our work consistent and high quality
Be the trusted advisor: Translate technical findings into clear, practical advice for both engineers and executives
Support the business: Help with scoping, proposals and pricing for new engagements
Give back: Represent Vanguard Cyber in the community through talks, CTFs, research, blog posts or open source tools
What we're looking for
Offensive experience: 3+ years in penetration testing or offensive security, ideally in a consulting environment, with experience running engagements independently
Technical breadth and depth: Strong across web applications, APIs, networks and Active Directory, with working knowledge of cloud (AWS, Azure or GCP) and a specialty or two you love
IT infrastructure skills: Hands-on experience administering and securing Microsoft 365 and Entra ID, networking and firewalls, and endpoint management in a small business environment
Mentoring: Experience or a genuine interest in mentoring juniors and reviewing others' work
Communication: You write clear, accurate reports and are comfortable presenting findings to anyone from developers to the board
Builder mindset: You enjoy creating structure from scratch and are comfortable wearing multiple hats in a growing business
Genuine interest: You stay engaged with the field outside of client work, through research, CTFs, conference talks, bug bounty, tooling or a home lab
Certifications: OSCP, CPTS, OSWE, OSEP, CRTO or CREST CRT are highly regarded
Clearance: An existing Australian Government security clearance (Baseline or NV1) is a bonus but not essential
Australian citizenship or otherwise full-time working rights required
What we offer
Competitive salary plus super, reflecting your experience
Real ownership and influence over the practice you're building, with a direct line to the founder
A dedicated training and certification budget for you and the team you grow
Paid time for research, tooling and community contributions
Fully remote working arrangement
A close-knit team that genuinely cares about doing good work and helping others break into the industry
How to set yourself apart
At our core, we're looking for people who genuinely care about the cybersecurity community and want to contribute to something bigger than themselves. For this role, that means someone who gets as much satisfaction from watching a junior land their first critical finding as from landing one themselves.
In your cover letter, tell us about a team, process or capability you've built or improved, and what you'd focus on in your first 90 days with us.
We look forward to hearing your story and good luck!