Senior Offensive Security Engineer: Red Team & Cloud Leader

Tradermath; New York, Northern (NY, KY); Hybrid; USD 175,000 - 275,000; Full time

Benefits offered by this job

Medical insurance

Dental and vision insurance

401(k) with match

Discretionary annual bonus

Job summary

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, adversary simulations, and exploit development. You will collaborate with security, infrastructure, and trading teams to translate findings into measurable improvements.

Ideal candidates bring 5+ years in offensive security, strong scripting, and experience with tools like Cobalt Strike, Metasploit, and Burp Suite. You will shape DRW's security methodology and mentor peers in a high-trust environment.

Qualifications

• 5+ years in offensive security, penetration testing, or red teaming with full engagement lifecycle.
• Strong scripting or programming ability for offensive tooling.
• Solid networking, Windows/macOS/Linux internals, identity providers, and cloud platforms.
• Hands-on use of common offensive security tools and a track record of building custom tooling when needed.
• Familiarity with MITRE ATT&CK, adversary emulation, and detection evasion techniques.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, corporate IT, and cloud environments.
• Conduct penetration tests across networks, web and internal applications, APIs, and cloud infrastructure.
• Design and build custom tooling, scripts, and exploits to emulate adversary behavior and test detections.
• Collaborate with Security Engineering and SOC in purple-team exercises to close gaps between attackers and defenders.
• Run social engineering and phishing simulations to measure security awareness.
• Identify, validate, and track vulnerabilities through remediation with owners.

Skills

Off Sec experience

Scripting

Networking basics

Windows/macOS/Linux

Security tooling

MITRE ATT&CK

Technical reporting

AI/ML security

Collaboration

Tools

Cobalt Strike

Metasploit

Burp Suite

Nmap

BloodHound

Job description

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, adversary simulations, and exploit development. You will collaborate with security, infrastructure, and trading teams to translate findings into measurable improvements.

Ideal candidates bring 5+ years in offensive security, strong scripting, and experience with tools like Cobalt Strike, Metasploit, and Burp Suite. You will shape DRW's security methodology and mentor peers in a high-trust environment.