Senior Offensive Security Engineer - Red Team Lead

Linuxconfig; Chicago (IL); On-site; USD 175,000 - 275,000; Full time

Benefits offered by this job

Group medical insurance

Dental and vision insurance

401(k) plan with employer match

Disability insurance

Job summary

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, plan adversary simulations, and test trading systems, IT, and cloud platforms. You will translate findings into actionable improvements and help mature DRW's offensive security program.

You will design custom tooling, collaborate with SOC, run phishing simulations, and track remediation with cross-functional teams to measurably harden the firm's defenses.

Qualifications

• 5+ years of hands-on offensive security, pentesting, or red teaming across full engagement lifecycle.
• Strong scripting or programming ability for building offensive tooling.
• Solid understanding of networking, Windows, macOS, and Linux internals, identity providers, and cloud platforms.
• Experience with common offensive security tools (Cobalt Strike, Metasploit, BloodHound, Burp Suite, Nmap).
• Familiarity with MITRE ATT&CK, adversary emulation, and detection evasion techniques.
• Experience with clear, concise reporting translating findings to risk for engineers and executives.
• Experience with smart contract auditing and blockchain security.
• Familiarity with AI/ML security risks, including adversarial attacks and prompt injection.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, IT, and cloud environments.
• Conduct penetration tests across networks, web and internal apps, APIs, and cloud infrastructure; report remediation guidance.
• Design and build custom tooling, scripts, and exploits to emulate adversary behavior.
• Collaborate with Security Engineering and SOC in purple-team exercises to close gaps.
• Run social engineering and phishing simulations to improve security awareness.
• Identify, prioritize, and track vulnerabilities through remediation with owners.

Skills

Scripting能力

Networking fundamentals

Windows

macOS

Linux internals

Cloud platforms

MITRE ATT&CK

Adversary emulation

Reporting skills

Offensive tooling

Tools

Cobalt Strike

Metasploit

BloodHound

Burp Suite

Nmap

Job description

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, plan adversary simulations, and test trading systems, IT, and cloud platforms. You will translate findings into actionable improvements and help mature DRW's offensive security program.

You will design custom tooling, collaborate with SOC, run phishing simulations, and track remediation with cross-functional teams to measurably harden the firm's defenses.