Find a job 
Featured Companies 
Featured Universities 
For Companies At a Glance
- Tasks: Lead high-impact penetration testing projects and mentor your team.
- Company: Join a top cyber security consultancy with a strong reputation.
- Benefits: Competitive salary, remote work, and opportunities for professional growth.
- Other info: Dynamic role with opportunities to engage with clients and enhance your skills.
- Why this job: Make a real difference in securing complex environments while working remotely.
- Qualifications: CHECK Team Leader certification and strong penetration testing experience required.
The predicted salary is between 80000 - 90000 £ per year.
We're working with a leading cyber security consultancy looking to grow their penetration testing capability with the addition of a CHECK Team Leader (CTL). This is an opportunity to join one of the UK’s largest CHECK-accredited, security-cleared testing environments, delivering high-impact testing across complex and highly secure customer estates. The role is primarily remote, with occasional onsite client engagements as required.
Salary: £80-90,000 DOE
Work Structure: Remote (with UK client visits)
Security Clearance: Active or previously held DV clearance is essential.
The Role: You’ll be responsible for delivering high-quality penetration testing across a range of environments, while acting as a senior technical presence within the team. Engagements will include:
- Infrastructure penetration testing
- Web application testing
- Internal and external network testing
- Active Directory / privilege escalation assessments
- Cloud security testing
- Red team style activities and security assessments
- CHECK-based testing within highly secure environments
You’ll also be involved in scoping engagements, supporting clients through remediation discussions, and contributing to the continued growth and quality of the testing practice.
What We're Looking For:
- Current CHECK Team Leader (CTL) certification
- Active DV clearance OR previously held DV clearance
- Strong hands-on penetration testing experience across infrastructure and applications
- Experience delivering testing within secure/government or high-assurance environments
- Strong client-facing communication skills
- Ability to write high-quality technical reports and communicate risk clearly
- Background working within a consultancy or dedicated security testing environment preferred
- Additional certifications such as CRT/CCT, OSCP, OSCE or similar are highly advantageous.
If this sounds like you, apply now for immediate consideration.
CHECK Team Leader - Penetration Testing in Gloucester employer: Oscar
Contact Detail:
Oscar Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land CHECK Team Leader - Penetration Testing in Gloucester
✨Tip Number 1
Network like a pro! Reach out to your connections in the cyber security field, especially those who are already in penetration testing roles. A friendly chat can lead to insider info about job openings or even referrals.
✨Tip Number 2
Show off your skills! Create a portfolio showcasing your penetration testing projects and any relevant certifications. This will give potential employers a clear view of what you bring to the table.
✨Tip Number 3
Prepare for interviews by brushing up on common penetration testing scenarios and case studies. We recommend practising your responses to technical questions and demonstrating your problem-solving skills.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets noticed. Plus, we love seeing candidates who take the initiative to connect directly with us.
We think you need these skills to ace CHECK Team Leader - Penetration Testing in Gloucester
Some tips for your application 🫡
Tailor Your CV: Make sure your CV is tailored to the CHECK Team Leader role. Highlight your penetration testing experience and any relevant certifications like CHECK Team Leader or OSCP. We want to see how your skills match what we're looking for!
Craft a Compelling Cover Letter: Your cover letter is your chance to shine! Use it to explain why you're the perfect fit for the role and how your experience aligns with our needs. Don’t forget to mention your active DV clearance if you have it!
Showcase Your Technical Skills: In your application, be sure to showcase your hands-on experience with various penetration testing techniques. We love seeing specific examples of your work, especially in secure environments. Let us know what you've achieved!
Apply Through Our Website: We encourage you to apply directly through our website for the best chance of getting noticed. It’s super easy, and we can’t wait to see your application come through!
How to prepare for a job interview at Oscar
✨Know Your Stuff
Make sure you brush up on your penetration testing skills and knowledge. Be ready to discuss specific techniques you've used in infrastructure and web application testing, as well as any experience with Active Directory assessments. The more detailed you can be about your hands-on experience, the better!
✨Showcase Your Leadership Skills
As a CHECK Team Leader, you'll need to demonstrate your ability to lead and mentor others. Prepare examples of how you've successfully managed teams or projects in the past, especially in high-pressure environments. Highlight your communication skills and how you've effectively engaged with clients.
✨Prepare for Technical Questions
Expect some tough technical questions during the interview. Brush up on the latest trends in cyber security, particularly around cloud security and red team activities. Being able to articulate your thought process when tackling complex problems will impress your interviewers.
✨Practice Your Reporting Skills
Since writing high-quality technical reports is crucial for this role, practice summarising complex findings clearly and concisely. You might even want to prepare a mock report to showcase your ability to communicate risks effectively. This will show that you can not only find vulnerabilities but also convey them to clients in an understandable way.