At a Glance
- 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, hybrid work model, and opportunities for professional growth.
- Other info: Join a collaborative environment with a focus on innovation and quality.
- Why this job: Shape the future of penetration testing while influencing a growing team.
- Qualifications: Strong background in penetration testing and leadership experience required.
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
- Hands-on experience delivering client-facing penetration testing engagements
- 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. If this sounds like you, apply now!
Head of Penetration Testing (Hands-on) in Northampton employer: Oscar Associates (UK) Limited
Join a dynamic and innovative cyber security consultancy in London, where you will not only lead the penetration testing function but also remain hands-on with the latest tools and technologies. Our collaborative work culture fosters continuous learning and professional growth, offering you the chance to mentor emerging talent while shaping the future of our offensive security practice. With competitive compensation and a hybrid working model, this is an excellent opportunity for those looking to make a meaningful impact in the field of cyber security.
Contact Detail:
Oscar Associates (UK) Limited Recruiting Team
StudySmarter Expert Advice🤫
We think this is how you could land Head of Penetration Testing (Hands-on) in Northampton
✨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 that perfect Head of Pen Testing role!
✨Tip Number 2
Show off your skills! Create a portfolio showcasing your penetration testing projects. Whether it's a blog, GitHub repo, or case studies, let potential employers see what you can do. This is your chance to shine and demonstrate your hands-on expertise.
✨Tip Number 3
Prepare for those interviews! Brush up on your technical knowledge and be ready to discuss your past experiences in detail. Practice common interview questions and think about how you can convey your leadership style while still being hands-on.
✨Tip Number 4
Don't forget to apply through our website! We’ve got loads of opportunities waiting for you. Plus, applying directly shows your enthusiasm and commitment to joining our team. So, what are you waiting for? Get your application in!
We think you need these skills to ace Head of Penetration Testing (Hands-on) in Northampton
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 and leadership qualities, as we want to see how you can lead our team while still being technically involved.
Craft a Compelling Cover Letter:Your cover letter is your chance to shine! Use it to explain why you're passionate about penetration testing and how your background makes you the perfect fit for this role. We love seeing enthusiasm and a clear understanding of what we do.
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 looking for someone who can hit the ground running and lead our technical delivery.
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 regarding your application status!
How to prepare for a job interview at Oscar Associates (UK) Limited
✨Know Your Stuff
Make sure you brush up on your penetration testing skills and methodologies. Be ready to discuss specific tools and techniques you've used in past engagements, as well as any challenges you've faced and how you overcame them.
✨Show Leadership Potential
Since this role involves leading a team, be prepared to talk about your experience mentoring others. Share examples of how you've developed junior testers or influenced team dynamics, showcasing your ability to lead while still being hands-on.
✨Engage with the Client Mindset
Understand the importance of client engagement in this role. Be ready to discuss how you would approach scoping and delivering high-quality reports that cater to both technical and non-technical stakeholders. This shows you can bridge the gap between technical delivery and client satisfaction.
✨Certifications Matter
Highlight your relevant certifications, especially if you hold multiple ones like CREST CRT, OSCP, or CHECK Team Leader. These not only validate your expertise but also demonstrate your commitment to the field, which is crucial for a leadership position.
