Senior Offensive Security Engineer - Red Team Lead

Drweng; New York (NY); On-site; USD 175,000 - 275,000; Full time

Benefits offered by this job

Group medical insurance

Dental and vision insurance

401k with discretionary match

Discretionary annual bonus

Life and AD&D insurance

Health savings accounts

Job summary

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, penetration tests, and adversary simulations across trading, corporate IT, and cloud environments. You will translate findings into real improvements and shape the offensive security roadmap with the security and trading teams.

You will design custom tooling, run phishing simulations, and stay ahead of threat trends, including AI/LLM risks, while mentoring other engineers in security best practices.

Qualifications

• 5+ years of hands-on experience in offensive security, penetration testing, or red teaming.
• Strong scripting or programming ability for building offensive tooling.
• Solid understanding of networking fundamentals, Windows, macOS, and Linux internals, identity providers, and cloud platforms.
• Practical experience with common offensive security tools (e.g., Cobalt Strike, Metasploit, BloodHound, Burp Suite, Nmap) and a track record of building your own when needed.
• Working knowledge of MITRE ATT&CK, adversary emulation, and detection evasion techniques; understanding defensive controls.
• Track record of clear, precise reporting translating findings into risk understood by engineers and executives.
• Experience with smart contract auditing and blockchain security.
• Familiarity with AI/ML security risks including adversarial attacks and prompt injection.
• Collaborative mindset: red teaming to improve overall security.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, corporate IT, and cloud environments, modeling attacker TTPs.
• Conduct penetration tests across networks, web and internal applications, APIs, and cloud infrastructure with actionable remediation guidance.
• Design and build custom tooling, scripts, and exploits to emulate adversary behavior and test control effectiveness.
• Partner with Security Engineering and SOC in purple-team exercises to close gaps between attackers and defenders.
• Run social engineering and phishing simulations to assess and improve security awareness.
• Identify, validate, prioritize, and track vulnerabilities through remediation with owners.
• Present engagement results and risk narratives to technical teams and senior leadership.
• Stay current on threat landscape, emerging TTPs, and offensive tooling.
• Assess security of AI/LLM-integrated systems and harden them.
• Leverage AI-assisted tooling to accelerate reconnaissance and exploit development.
• Help define and mature DRW’s offensive security methodology, standards, and tooling, and mentor engineers.

Skills

Offensive security

Penetration testing

Red teaming

Scripting

Communication

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, corporate IT, and cloud environments. You will translate findings into real improvements and shape the offensive security roadmap with the security and trading teams.

You will design custom tooling, run phishing simulations, and stay ahead of threat trends, including AI/LLM risks, while mentoring other engineers in security best practices.