Head of Penetration Testing (Hands-on)

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

Considering making an application for this job Check all the details in this job description, and then click on Apply.
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. xwzovoh
To understand more about what we do with your data please review our privacy policy in the privacy section of the Oscar website.