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- Tasks: Lead and scale the penetration testing function while staying hands-on with technical delivery.
- Company: Dynamic cyber security consultancy focused on offensive security.
- Benefits: Competitive salary of £85,000, hybrid work model, and opportunities for professional growth.
- Why this job: Shape the future of penetration testing while influencing a talented team.
- Qualifications: Strong background in penetration testing and leadership experience required.
- Other info: Join a growing team and make a real impact in the cyber security landscape.
The predicted salary is between 85000 - 85000 £ per year.
We’re working with a growing cyber security consultancy looking to hire a Head of Penetration Testing to lead and scale their offensive security capability. This is a hands‑on leadership role, ideal for someone from a strong penetration testing background who wants to step into a position where they can own technical delivery, shape a team, and influence the direction of a testing practice - without stepping away from the tools.
The Role: You’ll take ownership of the organisation’s penetration testing function, leading from the front on technical delivery, quality standards, and team development. This role is best suited to someone who is already operating as a Senior / Lead Penetration Tester or CHECK Team Leader, and is looking to step into a broader leadership position while remaining technically hands‑on. You’ll play a key role in defining methodologies, mentoring testers, engaging clients, and driving the growth of the penetration testing offering.
Key Responsibilities:
- Lead and scale the penetration testing function (people, processes, tooling)
- Deliver and oversee high‑quality penetration testing engagements (web, infrastructure, cloud, application)
- Act as a technical authority across offensive security engagements
- Ensure consistency and quality across all reports and deliverables
- Support pre‑sales, scoping and client engagements
- Mentor and develop a team of penetration testers
- Manage utilisation, capacity, and technical performance of the team
- Contribute to service development and growth of the practice
Key Skills & Experience:
- Strong background in penetration testing (offensive security) across web, infrastructure, and cloud
- Experience operating at Senior / Lead Pen Tester or CHECK Team Leader level
- Strong reporting skills and ability to communicate findings to both technical and non‑technical stakeholders
- Experience mentoring or leading testers
Certifications (essential):
- Candidates must hold two or more of the following (or equivalent):
- CREST CRT or CCT
- OSCP
- OSCE / OSWE
- CISSP
- CHECK Team Member (CTM) or CHECK Team Leader (CTL)
Why Join?
This is an opportunity to step into a role where you can shape and lead a penetration testing function, not just deliver within one. You’ll have the autonomy to influence how the practice evolves, while still staying close to the technical work that got you here.
Head of Penetration Testing employer: Oscar
Contact Detail:
Oscar Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Head of Penetration Testing
✨Tip Number 1
Network like a pro! Get out there and connect with folks in the cyber security scene. Attend meetups, conferences, or even online webinars. You never know who might have the inside scoop on a Head of Pen Testing role!
✨Tip Number 2
Show off your skills! Create a portfolio showcasing your penetration testing projects and methodologies. This will not only highlight your expertise but also give potential employers a taste of what you can bring to their team.
✨Tip Number 3
Don’t just apply, engage! When you find a job that excites you, reach out to the hiring manager or someone in the company. A quick message expressing your interest can set you apart from the crowd and show your enthusiasm.
✨Tip Number 4
Keep it real during interviews! Be prepared to discuss your hands-on experience and how you've led teams in the past. Show them you’re not just about the theory but can deliver results in the trenches too!
We think you need these skills to ace Head of Penetration Testing
Some tips for your application 🫡
Tailor Your CV: Make sure your CV reflects the skills and experiences that align with the Head of Penetration Testing role. Highlight your hands-on experience in penetration testing and any leadership roles you've held, as we want to see how you can lead our team.
Craft a Compelling Cover Letter: Your cover letter is your chance to shine! Use it to explain why you're passionate about offensive security and how your background makes you the perfect fit for this role. We love seeing enthusiasm and a clear vision for the future.
Showcase Your Technical Skills: Don’t shy away from detailing your technical expertise in penetration testing. Mention specific tools and methodologies you’ve used, as we’re keen on candidates who can lead from the front while still being hands-on with the tech.
Apply Through Our Website: We encourage you to apply directly through our website. It’s the best way for us to receive your application and ensures you don’t miss out on any important updates during the process. Plus, we love seeing applications come through our own channels!
How to prepare for a job interview at Oscar
✨Know Your Stuff
Make sure you brush up on your technical skills and knowledge in penetration testing. Be ready to discuss specific tools and methodologies you've used, as well as any challenges you've faced in previous roles. This will show that you're not just a leader but also someone who can get hands-on when needed.
✨Showcase Your Leadership Style
Prepare to talk about your approach to leading teams and mentoring testers. Think of examples where you've successfully developed team members or improved processes. This is your chance to demonstrate how you can shape the penetration testing function while still being technically involved.
✨Engage with Real Scenarios
Be ready to discuss real-world scenarios or case studies from your past experiences. This could involve explaining how you handled a complex penetration test or how you communicated findings to both technical and non-technical stakeholders. It’s all about showing your problem-solving skills and your ability to convey technical information clearly.
✨Ask Insightful Questions
Prepare some thoughtful questions about the company's current penetration testing practices and future goals. This shows your genuine interest in the role and helps you understand how you can contribute to their growth. Plus, it gives you a chance to assess if the company aligns with your career aspirations.