Senior Offensive Security Engineer - Red Team Lead

DRW Trading Group; City Of London; On-site; GBP 90,000 - 130,000; Full time

Job summary

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, penetration tests, and adversary simulations across trading systems, IT, and cloud platforms. You will design tooling, translate findings into actionable improvements, and work closely with security, infrastructure, and trading teams to strengthen defenses.

You will help shape DRW’s offensive security approach, stay ahead of evolving threats, and mentor other engineers while advancing the firm’s security maturity.

Qualifications

• 5+ years of hands-on offensive security experience including full engagement lifecycle: reconnaissance, initial access, privilege escalation, lateral movement, persistence, exfiltration.
• Strong scripting or programming ability for building/adapting offensive tooling.
• Solid understanding of networking fundamentals and OS internals (Windows, macOS, Linux); cloud platforms.
• Practical experience with common offensive security tools and a track record of building custom tooling when needed.
• Working knowledge of MITRE ATT&CK, adversary emulation, and detection evasion; ability to translate findings into risk for engineers and executives.
• Experience with smart contract auditing and blockchain security.
• Familiarity with AI/ML security risks including prompt injection and model manipulation.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, IT, and cloud environments, aligning with MITRE ATT&CK.
• Conduct comprehensive penetration tests across networks, web and internal apps, APIs, and cloud infrastructure, delivering clear remediation guidance.
• Design and build custom tooling and exploits to simulate attacker behavior and validate detections.
• Collaborate with Security Engineering and SOC teams in purple-team exercises to close gaps.
• Run social engineering and phishing simulations to improve security awareness.
• Identify, validate, and track vulnerabilities through remediation with stakeholders.
• Present results and risk narratives to technical teams and senior leadership.
• Stay current on threat landscape and offensive tooling; contribute to DRW's security roadmap.
• Assess AI/LLM-integrated systems security and harden them alongside product teams.
• Leverage AI-assisted tooling to accelerate reconnaissance and exploit development.
• Help mature DRW’s offensive security methodology, standards, and tooling; mentor others.

Skills

5+ years of offensive security

Scripting & programming

Networking fundamentals

Windows/macOS/Linux internals

MITRE ATT&CK familiarity

Clear reporting

AI/ML security awareness

Collaborative mindset

Blockchain security experience

Tools

Cobalt Strike

Metasploit

BloodHound

Burp Suite

Nmap

Job description

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, penetration tests, and adversary simulations across trading systems, IT, and cloud platforms. You will design tooling, translate findings into actionable improvements, and work closely with security, infrastructure, and trading teams to strengthen defenses.

You will help shape DRW’s offensive security approach, stay ahead of evolving threats, and mentor other engineers while advancing the firm’s security maturity.