Senior Red Team Operator
UK (Remote-first, with occasional in-person meetups)
At JUMPSEC, we focus on how real attackers operate today, and help our clients understand where they’re genuinely exposed, not just where a checklist says they should worry.
We spend time understanding each organisation, their environment, and how they actually work. That lets us design red team engagements that make sense in context. No generic payloads, no copy-and-paste attack paths, just intelligence-led adversary simulation that’s realistic, relevant, and useful. We believe attack informs defence: our red team work is designed to give defenders actionable insight into attacker behaviour, helping them prioritise detection and response where it matters most.
The Role
We’re looking for a highly skilled Red Team Operator to join our adversary simulation team. This is a hands-on-keyboard role for someone who wants to spend their time doing the hard technical work: getting in quietly, moving carefully, and reaching objectives in mature, well-defended environments.
This is not a standard penetration testing role. You’ll be executing full-spectrum, intelligence-led red team operations across complex enterprise and hybrid environments, from initial access through phishing and social engineering to advanced Active Directory and cloud-native compromise. You’ll work alongside senior operators and our Technical Director, contributing your tradecraft, research, and tooling to every engagement.
This role suits someone who loves the craft: who follows emerging threat actors, picks apart new techniques as soon as they’re published, and enjoys making them work in the real world.
What you will be doing:
- Executing end-to-end red team and adversary simulation operations against large, mature organisations
- Gaining initial access through tailored phishing, payload delivery, and social engineering campaigns
- Performing advanced Active Directory and hybrid identity attacks, including trust abuse, credential access, and lateral movement
- Identifying and exploiting weaknesses across Microsoft 365, Entra ID, AWS, GCP, Okta, and SaaS platforms
- Operating stealthily against modern defensive controls (EDR/XDR, MFA, conditional access) using low-noise, well-considered techniques
- Building, adapting, and maintaining custom tooling for delivery, evasion, and C2
- Researching new techniques, abuse paths, and misconfigurations, and turning them into usable tradecraft
- Emulating the behaviour of specific real-world threat actors based on threat intelligence
- Supporting purple team exercises, helping client blue teams understand and detect what you did
- Writing clear, technically accurate findings with real attacker context
What we are looking for?
- Solid hands-on experience delivering red team operations, ideally in enterprise or regulated environments
- Deep practical knowledge of Active Directory, cloud identity, and hybrid enterprise attack paths
- Experience operating C2 frameworks (e.g. Cobalt Strike, Mythic, Sliver, or similar) and understanding how they work under the hood
- A good working grasp of EDR internals and evasion, and the judgement to know when to stay quiet
- Comfort writing or modifying tooling in at least one of C#, C/C++, Go, Rust, Python, or PowerShell
- Genuine interest in the threat landscape and new offensive research
- The ability to explain what you did, and why it matters, to defenders and client stakeholders
- Willing to lead and develop junior Red Team members
How we work:
- We prioritise quality over volume — engagements are carefully designed, not templated
- We operate with high trust and autonomy, with accountability for outcomes
- We take a research-led approach, staying ahead of adversaries
- Collaboration is central — working across red, blue, and leadership teams
- We maintain a low-ego, high-performance culture where ideas are constructively challenged
- Clear, effective communication is essential — internally and with clients
Leadership and behaviour expectations:
- Set and uphold a high technical and ethical standard
- Act as a mentor, supporting the development of others
- Demonstrate sound judgement under pressure
- Build strong, trusted relationships internally and externally
- Take ownership and drive work through to resolution
- Contribute to a culture of continuous improvement and knowledge sharing
What success looks like:
- We prioritise quality over volume — engagements are carefully designed, not templated
- We operate with high trust and autonomy, with accountability for outcomes
- We take a research-led approach, staying ahead of adversaries
- Collaboration is central — working across red, blue, and leadership teams
- We maintain a low-ego, high-performance culture where ideas are constructively challenged
- Clear, effective communication is essential — internally and with clients
Nice to have:
- Vulnerability research or proof-of-concept development
- Experience emulating specific real-world threat actors
- Contributions to open-source tools, blogs, whitepapers, or conference talks
- Experience on CBEST, TIBER-EU, GBEST, or similar intelligence-led testing engagements
- Certifications such as CRTO/CRTL, OSEP/OSCE3, CCSAS/CCRTS, or equivalent (valued, but not essential)
Growth and development:
- Dedicated training and research budget
- Access to internal labs, CTI, and tooling
- Opportunities to contribute to services, methodology, and tooling development
- Support for conference speaking, publishing, and community contributions
- Clear progression into technical leadership or research specialisation
- Dedicated training and research budget
Benefits:
- Competitive salary, depending on experience
- 25 days annual leave, plus your birthday off
- Flexible working, with national co-working spaces available when required
- Annual training and research budget
- Access to red team labs, CTI, and test infrastructure
- Recruitment referral scheme (earn up to £2,000)
- Company pension
Candidate profile:
- Naturally curious and research-driven
- Comfortable working in complex, ambiguous environments
- Motivated by real-world impact, not checkbox testing
- A strong communicator and problem solver
- Committed to continuous learning and technical excellence
Company Culture:
- Supportive, inclusive culture with a strong emphasis on trust and autonomy
- Senior, highly skilled peers and zero micromanagement
- Dedicated time to research, experiment, and stay ahead of emerging threats
- Opportunities to publish research, build tools, and shape the future of red teaming at JUMPSEC
How to apply
If you’re interested in joining JUMPSEC as a Senior Red Team Operator, please send a short cover letter outlining your experience, relevant skills, and why you’d be a great fit for our team to [email protected].
Please reference JSSenior RedTeam Operator in the subject line of your email.
UK-Based Role: We’re hiring within the UK and are looking for candidates who already hold the right to work in the UK. As part of our onboarding process, you’ll be asked to provide the relevant right-to-work documentation. Unfortunately, we are unable to offer visa sponsorship for this position.
To learn more about who we are and what we do, visit www.jumpsec.com.
Whilst we do our best to respond to every applicant, we occasionally receive a high volume of applications which can result in delays. If you have not heard from us within 20 working days, please assume that your application has been unsuccessful on this occasion. We sincerely appreciate the time and effort you have invested in applying and wish you every success in your job search.
At JUMPSEC, we believe that great people drive our success, and we embrace diversity and inclusion as integral parts of our company culture. We welcome individuals from all backgrounds, ethnicities, cultures, and genders. Diverse perspectives and ideas contribute to the uniqueness of our brand and enable the creative problem-solving that our clients value. Join us on our mission to create a safer digital world!