Senior Red Team Engineer, Offensive Security

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

Benefits offered by this job

Bonus opportunities

Medical, dental & vision insurance

401(k) plan with match

Disability insurance

Life & AD&D insurance

Health Savings Account

Flexible spending accounts

Job summary

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, pentests, and adversary simulations across trading, IT, and cloud environments. You will translate findings into concrete improvements and shape the offensive security program.

You will design tooling, run purple-team exercises, and mentor other engineers while staying ahead of threat trends and AI/ML security risks. This role emphasizes collaboration and measurable impact.

Qualifications

• 5+ years of hands-on offensive security, penetration testing, or red teaming across full engagement lifecycles.
• Strong scripting or programming ability for tooling.
• Solid understanding of networking, Windows, macOS, Linux internals, identity providers, and cloud platforms.
• Experience with common offensive security tools and building your own when needed.
• Working knowledge of MITRE ATT&CK, adversary emulation, and detection evasion techniques.
• Clear, precise reporting translating technical findings into risk for engineers and executives.
• Experience with smart contract auditing and blockchain security.
• Familiarity with AI/ML security risks and LLM-powered tooling.
• Collaborative mindset; red teaming to improve organizational security.

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 apps, APIs, and cloud infrastructure with actionable remediation guidance.
• Design and build custom tooling, scripts, and exploits to emulate adversary behavior and test detection coverage.
• Collaborate with Security Engineering and SOC in purple-team exercises to close gaps.
• Run social engineering and phishing simulations to improve security awareness.
• Identify 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; improve defenses.
• 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 and mentor others.

Skills

Offensive security

Red teaming

Penetration testing

Scripting

Programming

Networking fundamentals

Windows internals

macOS internals

Linux internals

Cloud platforms

MITRE ATT&CK

Reporting to executives

Blockchain security

AI/ML security

Social engineering

Smart contract auditing

Tools

Cobalt Strike

Metasploit

BloodHound

Burp Suite

Nmap

Job description

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, pentests, and adversary simulations across trading, IT, and cloud environments. You will translate findings into concrete improvements and shape the offensive security program.

You will design tooling, run purple-team exercises, and mentor other engineers while staying ahead of threat trends and AI/ML security risks. This role emphasizes collaboration and measurable impact.