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. 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Head of Penetration Testing (Hands-on) employer: Oscar Associates (UK) Limited
Join a leading specialist organisation in Digital Forensics located in the picturesque Stratford-upon-Avon, where you will be part of a dynamic team dedicated to tackling complex investigations. With a strong emphasis on employee growth, you will benefit from a structured environment that supports your technical development and offers a competitive salary alongside an attractive benefits package. This is an excellent opportunity for both emerging talents and seasoned professionals to engage in varied and technically stimulating cases while enjoying the charm of this historic town.
Contact Details:
Oscar Associates (UK) Limited Recruitment Team
StudySmarter Expert Advice🤫
We think this is how you could land Head of Penetration Testing (Hands-on)
✨Get Involved in the Cybersecurity Community
Diving into the cybersecurity community is key for landing that full-time gig. Join forums like Reddit's r/cybersecurity or attend local meetups to connect with industry veterans and other job seekers. Networking is everything in this field—don’t just be a passive lurker!
✨Show Off Your Skills with Capture the Flag Competitions
Participate in Capture the Flag (CTF) competitions; these are not just a fun way to boost your skills but also a chance to showcase your talent to potential employers. Many companies, including Oscar Associates (UK) Limited, love seeing candidates who actively engage in these challenges.
✨Tailor Your Online Presence
Make sure your LinkedIn and any professional profiles reflect your cybersecurity expertise. Share your projects, whether they’re personal or from a previous role, to catch the eye of hiring managers. This is how they’ll find your passion and commitment to the field!
✨Apply Directly Through Oscar Associates (UK) Limited
Don’t forget to head straight to our website and check out any openings for cybersecurity roles at Oscar Associates (UK) Limited. Applying directly can sometimes give you an edge, especially if you can mention that you've been following our work or engaging in the community.
Some tips for your application 🫡
Show off your technical skills:In cybersecurity, it's crucial to highlight your technical prowess. Make sure your CV showcases specific skills like network security, penetration testing, or threat analysis. If you have relevant certifications (like CEH or CISSP), pop those on the front page to grab attention!
Tailor your portfolio for the role:Even for a full-time role, a portfolio can set you apart. If you've worked on any cybersecurity projects—be it CTF challenges, security assessments, or research papers—include these in your application. This demonstrates not just your skills, but also your hands-on experience!
Use real-world examples:When writing your cover letter, don’t just stick to your qualifications. Share real-world examples of how you’ve tackled security issues or vulnerabilities. This gives the hiring team at Oscar Associates (UK) Limited insight into your practical problem-solving abilities and makes your application memorable.
Demonstrate your passion for cybersecurity:Cybersecurity is an ever-evolving field, so show us that you’re always learning! Mention any recent courses, webinars, or industry events you’ve attended. This not only exhibits your enthusiasm but also signals to Oscar Associates (UK) Limited that you’re committed to staying ahead in the game.
How to prepare for a job interview at Oscar Associates (UK) Limited
✨Sharpen Your Technical Skills
For a role in cybersecurity, it’s essential to be up-to-date with the latest tools and techniques. Brush up on your knowledge of firewalls, intrusion detection systems, and vulnerability assessment tools. Be ready to discuss specific scenarios where you’ve applied these skills, as hands-on experience can really set us apart in interviews.
✨Prepare for Scenario-Based Questions
Expect the interviewers at Oscar Associates (UK) Limited to throw in some hypothetical situations to see how you’d handle them. Think about common security breaches or incidents and be prepared to explain how you would respond. This not only shows your problem-solving skills but also your understanding of real-world cybersecurity challenges.
✨Highlight Your Certifications
Certifications like CompTIA Security+, CISSP, or CEH can give you a significant edge in a full-time role in cybersecurity. Make sure to mention these during your interview and be prepared to discuss what you learned through those certifications and how they relate to the position at Oscar Associates (UK) Limited.
✨Show Your Passion for Cybersecurity
Since you’re going for a full-time gig, showing genuine enthusiasm for the field can make all the difference. Share any personal projects, blogs, or communities you’re part of that relate to cybersecurity. This not only showcases your passion but also your commitment to staying engaged in this ever-evolving field.
