Head of Penetration Testing (Hands-on)

Head of Penetration Testing (Hands-on) in London | Oscar Associates (UK) Limited Search Search These jobs were popular with other job seekers Senior Security Risk Assurance Manager Sanderson Government and Defence City of London (EC1), EC1 Additional Benefits 3 days ago Lead Cyber Security Consultant (Defence) Sanderson Government and Defence South West Excellent Benefits 1 month ago Tax Assurance & Risk Management Senior Manager BDO Birmingham (B30), B30 2XS competitive salary and package 2 weeks ago Cybersecurity Operations Lead Thales Group South West Competitive 1 week ago Senior Cyber Security Consultant Atkins Bristol, Avon Competitive 2 weeks ago IT Disaster Recovery Consultant, Hybrid 2 days Sanderson Recruitment Gloucester (GL1), GL1 £500 - £1000 per day + Market Rate 3 days ago Cyber Incident Response Manager Ashdown Group City of London (EC2N), EC2N £100,000 4 days ago Head of Security Engineering Holland & Barrett London Competitive 1 week ago Security Assurance Analyst Henderson Scott Hampshire Up to £550 per day 1 month ago Information and Technology Governance & Risk Lead DS SMITH PACKAGING LIMITED Milton Keynes (MK9), MK9 3GA Competitive + benefits 1 day ago Senior Security Risk Assurance Manager Sanderson Government and Defence City of London (EC1), EC1 Additional Benefits 3 days ago Lead Cyber Security Consultant (Defence) Sanderson Government and Defence South West Excellent Benefits 1 month ago Tax Assurance & Risk Management Senior Manager BDO Birmingham (B30), B30 2XS competitive salary and package 2 weeks ago Cybersecurity Operations Lead Thales Group South West Competitive 1 week ago Senior Cyber Security Consultant Atkins Bristol, Avon Competitive 2 weeks ago IT Disaster Recovery Consultant, Hybrid 2 days Sanderson Recruitment Gloucester (GL1), GL1 £500 - £1000 per day + Market Rate 3 days ago Cyber Incident Response Manager Ashdown Group City of London (EC2N), EC2N £100,000 4 days ago Head of Security Engineering Holland & Barrett London Competitive 1 week ago Security Assurance Analyst Henderson Scott Hampshire Up to £550 per day 1 month ago Information and Technology Governance & Risk Lead DS SMITH PACKAGING LIMITED Milton Keynes (MK9), MK9 3GA Competitive + benefits 1 day ago Head of Penetration Testing (Hands-on) Oscar Associates (UK) Limited London; City of London; East London; Central London; South East London; West London; Canary Wharf; South West London; North London; Greenwich; Stratford Permanent Published: 3 days ago £80000 - £85000 per annum Head of Penetration Testing (Hands-on) Oscar Associates (UK) Limited 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. Similar Head Of Penetration Testing (Hands Jobs Popular with Other Job Seekers Senior Security Risk Assurance Manager Sanderson Government and Defence City of London (EC1), EC1 Additional Benefits 3 days ago Lead Cyber Security Consultant (Defence) Sanderson Government and Defence South West Excellent Benefits 1 month ago Tax Assurance & Risk Management Senior Manager BDO Birmingham (B30), B30 2XS competitive salary and package 2 weeks ago Cybersecurity Operations Lead Thales Group South West Competitive 1 week ago Senior Cyber Security Consultant Atkins Bristol, Avon Competitive 2 weeks ago IT Disaster Recovery Consultant, Hybrid 2 days Sanderson Recruitment Gloucester (GL1), GL1 £500 - £1000 per day + Market Rate 3 days ago Cyber Incident Response Manager Ashdown Group City of London (EC2N), EC2N £100,000 4 days ago Head of Security Engineering Holland & Barrett London Competitive 1 week ago Security Assurance Analyst Henderson Scott Hampshire Up to £550 per day 1 month ago Information and Technology Governance & Risk Lead DS SMITH PACKAGING LIMITED Milton Keynes (MK9), MK9 3GA Competitive + benefits 1 day ago Management jobs Management jobs in London Technical jobs Technical jobs in London Jobs in London Totaljobs About us Work for us Media centre Partners Jobseeker Jobs Jobseeker login Salary Planner Jobseeker help centre Career advice Recruiter Courses Advertise a job Recruiter login Contact us – recruiters Recruiter advice Recruit internationally Let's connect Apps Privacy policy Terms and conditions Cookies Compliance Accessibility The Stepstone Group UK Ltd © 2026