Senior Offensive Security Engineer — Red Team Leader & Tooling

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

Benefits offered by this job

Medical insurance

Pharmacy

Dental & Vision Insurance

401k with employer match

Disability insurance

Life & AD&D

HSA

FSA

Job summary

DRW, a Chicago-based trading firm, is expanding its offensive security program and seeks a Senior Offensive Security Engineer to lead red-team engagements, tests, and adversary simulations across trading systems and cloud platforms.

You will design methods, build tooling, and guide improvements with security teams, helping to make the firm harder to compromise. Strong collaboration and clear communication are essential.

Qualifications

• 5+ years of hands-on experience in offensive security, penetration testing, or red teaming.
• Strong scripting or programming ability for building tooling.
• Solid understanding of networking, Windows/macOS/Linux internals, identity providers, and cloud platforms.
• Practical experience with offensive security tools (Cobalt Strike, Metasploit, BloodHound, Burp Suite, Nmap).
• Familiarity with MITRE ATT&CK, adversary emulation, and detection evasion techniques.
• Clear reporting and communication translating findings into actionable risk for engineering and executives.
• Experience with smart contract auditing and blockchain security.
• Familiarity with AI/ML security risks including adversarial attacks and prompt injection.
• Collaborative mindset to improve security posture across the organization.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, corporate IT, and cloud environments.
• Conduct penetration tests across networks, web apps, APIs, and cloud infrastructure with actionable remediation guidance.
• Design and build tooling, scripts, and exploits to emulate adversaries and test detection.
• collaborate with Security Engineering and SOC in purple-team exercises to close gaps.
• Run social engineering and phishing simulations to improve security awareness.
• Identify, validate, prioritize, and track vulnerabilities through remediation with owners.
• Present engagement results and risk narratives to technical teams and leadership.
• Stay current on threat landscape and offensive tooling, updating DRW’s defenses.
• Assess security of AI/LLM-integrated systems and harden them.
• Leverage AI-assisted tooling to speed reconnaissance and exploit development.
• Help define and mature DRW’s offensive security methodology and mentor engineers.

Skills

Offensive security

Red team testing

Scripting/programming

Networking fundamentals

OS internals

MITRE ATT&CK

Reporting & communication

Smart contract auditing

AI/ML security risks

Collaborative mindset

Tools

Cobalt Strike

Metasploit

BloodHound

Burp Suite

Nmap

Job description

DRW, a Chicago-based trading firm, is expanding its offensive security program and seeks a Senior Offensive Security Engineer to lead red-team engagements, tests, and adversary simulations across trading systems and cloud platforms.

You will design methods, build tooling, and guide improvements with security teams, helping to make the firm harder to compromise. Strong collaboration and clear communication are essential.