Senior Red Team Engineer — Offensive Security Lead

DRW Holdings, LLC; Chicago (IL); 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

Disability insurance

Health savings account (HSA)

Flexible spending accounts (FSA)

Job summary

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, pen tests, and adversary simulations across trading systems, IT, and cloud platforms. You will translate findings into real improvements and help shape tooling and roadmap for offensive security at DRW.

You will work with security, infrastructure, and trading teams to ensure controls are effective and drive actionable risk reductions. This is a hands-on, high-trust role focused on measurable improvement.

Qualifications

• 5+ years in offensive security, penetration testing, or red teaming across full engagement lifecycle.
• Strong scripting or programming ability for offensive tooling.
• Solid networking, OS internals, cloud platforms and identity providers knowledge.
• Experience with MITRE ATT&CK, reporting, and adversary emulation techniques.
• Familiarity with blockchain security and AI/ML security risks.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, IT and cloud environments.
• Perform penetration tests across networks, web apps, APIs, and cloud infrastructure with actionable remediation guidance.
• Design and build tooling, scripts, and exploits to emulate attacker behavior and test detections.
• Collaborate with Security Engineering and SOC in purple-team exercises to close gaps.
• Run phishing simulations and assess security awareness.
• Identify and track vulnerabilities through remediation with owners.

Skills

Red teaming

Penetration testing

Scripting

Networking

MITRE ATT&CK

Reporting

Cloud security

Blockchain security

AI/ML security

Team collaboration

Tools

Cobalt Strike

Metasploit

BloodHound

Burp Suite

Nmap

Job description

DRW is seeking a Senior Offensive Security Engineer to lead red team engagements, pen tests, and adversary simulations across trading systems, IT, and cloud platforms. You will translate findings into real improvements and help shape tooling and roadmap for offensive security at DRW.

You will work with security, infrastructure, and trading teams to ensure controls are effective and drive actionable risk reductions. This is a hands-on, high-trust role focused on measurable improvement.