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 Cheltenham employer: Oscar
Contact Detail:
Oscar Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land CHECK Team Leader - Penetration Testing in Cheltenham
✨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 Cheltenham
Some tips for your application 🫡
Tailor Your CV: Make sure your CV highlights your relevant experience in penetration testing and any CHECK certifications you hold. We want to see how your skills match up with what we're looking for, so don’t be shy about showcasing your achievements!
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 CHECK Team Leader role. Share specific examples of your past work and how it relates to the responsibilities outlined in the job description.
Show Off Your Communication Skills: Since this role involves client-facing interactions, make sure your application reflects your ability to communicate complex technical concepts clearly. We love candidates who can write high-quality reports and engage effectively with clients.
Apply Through Our Website: We encourage you to apply directly through our website for the best chance of getting noticed. It’s the quickest way for us to receive your application and start the conversation about your future with StudySmarter!
How to prepare for a job interview at Oscar
✨Know Your Stuff
Make sure you brush up on your penetration testing skills and the specific methodologies used in CHECK-based testing. Be ready to discuss your hands-on experience with infrastructure, web applications, and cloud security testing. This will show that you’re not just familiar with the concepts but can apply them effectively.
✨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 client-facing communication skills and how you've navigated remediation discussions.
✨Prepare for Technical Questions
Expect some deep technical questions during the interview. Brush up on topics like Active Directory assessments and privilege escalation techniques. Being able to articulate your thought process and problem-solving approach will impress the interviewers and show your expertise.
✨Ask Insightful Questions
Interviews are a two-way street! Prepare thoughtful questions about the company’s approach to penetration testing, their client base, and how they support professional development. This not only shows your interest in the role but also helps you gauge if the company is the right fit for you.