Head of Penetration Testing (Hands-on)

Hands on Head of Pen Testing | £85,000 | London, Hybrid

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 equivilant)

• 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!

Oscar Associates (UK) Limited is acting as an Employment Agency in relation to this vacancy.

To understand more about what we do with your data please review our privacy policy in the privacy section of the Oscar website.