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- Tasks: Conduct penetration tests on web apps, APIs, and infrastructure while leading client engagements.
- Company: Join a leading UK consultancy in offensive security with a dynamic team of 70 experts.
- Benefits: Enjoy a competitive salary, remote work, travel expenses, and clearance sponsorship.
- Other info: Flexible roles available with excellent career growth and mentorship opportunities.
- Why this job: Make a real impact in cybersecurity while working on diverse and exciting projects.
- Qualifications: Experience in penetration testing and strong communication skills are essential.
The predicted salary is between 55000 - 90000 £ per year.
Location: Fully Remote, UK (with client site visits as required)
Salary: £55,000 - £90,000 DOE
Type: Permanent, Full-Time
Summary: We are looking for experienced Penetration Testers to join one of the UK's larger dedicated offensive security practices. With a team of around 70 testers split across CHECK and CREST work, this is a well-established consultancy delivering high-quality assessments across a broad client base, with genuine variety in engagement type, sector, and technical depth. The team is structured across two streams, more commercially-driven engagements through CREST, and deeper, security-led work through CHECK, so there's a clear path whichever direction you want to lean. Multiple roles are available across mid and senior levels, and the company is flexible on starting clearance level.
No two weeks look the same.
Key Responsibilities:- Deliver web application, API, and infrastructure penetration tests, taking ownership of engagements end-to-end from scoping through to final report delivery.
- Lead client-facing engagements, communicating high-risk findings as they are identified to support swift remediation.
- Produce clear, professional reports tailored to client-specific context and business risk.
- Support broader offensive security activities including red and purple team engagements, phishing simulations, and assumed-breach style assessments where relevant.
- Contribute to internal QA, mentor more junior consultants, and support report quality across the team.
- Stay up to date with the evolving threat landscape and contribute to internal R&D, tooling, and knowledge sharing.
- CHECK Team Member (CTM), CHECK Team Leader (CTL), CREST Registered Tester (CRT), or CREST Certified Tester (CCT) qualified, or actively progressing along either pathway at a senior level.
- Hands-on experience delivering web application, API, and/or infrastructure penetration tests in a professional consultancy setting.
- Strong understanding of common vulnerability classes (e.g. OWASP Top 10), exploitation techniques, and remediation guidance.
- Confident client-facing communication skills, with the ability to explain technical findings to both technical and non-technical audiences.
- Strong written reporting skills, with the ability to produce clear, well-structured deliverables.
- A genuine passion for offensive security, demonstrated through CTFs, labs (e.g. Hack The Box, TryHackMe), research, certifications, or community involvement.
Clearance requirements vary by role, some do not require any clearance, others are looking for SC or DV. The company will put successful candidates through the relevant clearance process where required, so existing clearance is welcomed but not essential across the board.
Benefits:- Salary: £55,000 - £90,000, depending on experience, certifications and clearance level
- Fully remote working
- Overnight bonus for client site visits
- Travel and expenses covered for client work
- Clearance sponsorship (SC / DV) where required for the role
- Company pension scheme
Penetration Tester (CHECK / CREST) employer: Oscar Associates Limited
Contact Detail:
Oscar Associates Limited Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Penetration Tester (CHECK / CREST)
✨Tip Number 1
Network like a pro! Reach out to your connections in the cybersecurity field, attend relevant meetups or webinars, and don’t be shy about asking for introductions. We all know that sometimes it’s not just what you know, but who you know!
✨Tip Number 2
Show off your skills! Create a portfolio showcasing your penetration testing projects, whether they’re from CTFs, labs, or personal projects. This gives potential employers a taste of what you can do and sets you apart from the crowd.
✨Tip Number 3
Prepare for interviews by brushing up on your client-facing communication skills. Practice explaining complex technical concepts in simple terms. Remember, we want to demonstrate that we can effectively communicate findings to both techies and non-techies alike!
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets seen by the right people. Plus, we love seeing candidates who are proactive and engaged with our process!
We think you need these skills to ace Penetration Tester (CHECK / CREST)
Some tips for your application 🫡
Tailor Your CV: Make sure your CV reflects the skills and experiences that match the Penetration Tester role. Highlight your CHECK/CREST qualifications and any relevant projects you've worked on. We want to see how you can bring value to our team!
Craft a Compelling Cover Letter: Your cover letter is your chance to shine! Use it to explain why you're passionate about offensive security and how your background makes you a great fit for us. Keep it professional but let your personality show through.
Showcase Your Technical Skills: In your application, don't forget to mention specific tools and techniques you're familiar with, especially those related to web application and API testing. We love seeing candidates who are up-to-date with the latest in the threat landscape!
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. Plus, we’re excited to see what you bring to the table!
How to prepare for a job interview at Oscar Associates Limited
✨Know Your Stuff
Make sure you brush up on your technical skills, especially around web application, API, and infrastructure penetration testing. Be ready to discuss specific vulnerabilities like those in the OWASP Top 10 and share examples of how you've tackled them in past roles.
✨Client Communication is Key
Since this role involves client-facing engagements, practice explaining complex technical findings in a way that non-technical clients can understand. Think about how you would communicate high-risk issues and remediation strategies clearly and effectively.
✨Show Your Passion
Demonstrate your genuine interest in offensive security. Bring up any Capture The Flag (CTF) competitions, labs you've participated in, or relevant certifications. This shows you're not just in it for the job but truly care about the field.
✨Prepare for the Unexpected
Given the variety of work in this role, be ready for questions that might not directly relate to your experience. Think about how you would approach different scenarios, such as leading a red team engagement or contributing to internal R&D efforts.