Lead Red Team Engineer - Offensive Security

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

Benefits offered by this job

Medical Insurance

Dental & Vision

401k with match

Disability Insurance

Life Insurance

HSA & FSA

Job summary

DRW in Chicago is seeking a Senior Offensive Security Engineer to lead red team engagements, perform penetration tests, and simulate adversaries across trading systems, corporate IT, and cloud platforms. You will act as a trusted adversary to identify weaknesses before attackers do.

You will translate findings into actionable improvements, help shape DRW's offensive security roadmap, and collaborate with security, infrastructure, and trading teams.

Qualifications

• 5+ years in offensive security, pentesting, or red teaming throughout full engagement lifecycle.
• Strong scripting or programming ability for tooling.
• Solid networking, Windows/macOS/Linux internals, identity providers, and cloud platforms.
• Experience with offensive security tools and building custom tooling.
• Clear reporting translating findings to risk for engineers and executives.
• Experience with smart contract auditing and blockchain security.

Responsibilities

• Plan and execute red team engagements and adversary simulations against trading systems, corporate IT, and cloud environments, modeling realistic attacker tactics, techniques, and procedures (TTPs) mapped to frameworks such as MITRE ATT&CK
• Conduct penetration tests across networks, web and internal applications, APIs, and cloud infrastructure, and report findings with clear, actionable remediation guidance
• Design and build custom tooling, scripts, and exploits to emulate adversary behavior, test control effectiveness, and validate detection coverage
• Partner with the Security Engineering and SOC teams in purple-team exercises to close gaps between what attackers can do and what defenders can see
• Run social engineering and phishing simulations to assess and improve organizational security awareness
• Identify, validate, prioritize, and track vulnerabilities and control weaknesses through to remediation in collaboration with infrastructure, platform, and application owners
• Present engagement results and risk narratives to both technical teams and senior leadership in a way that drives action
• Stay current on the threat landscape, emerging TTPs, and offensive tooling, and bring that knowledge back into DRW’s defenses
• Assess the security of AI and LLM-integrated systems, including prompt injection, model manipulation, data poisoning, and abuse of agentic workflows, and work with teams building these systems to harden them
• Leverage AI‑assisted tooling to accelerate reconnaissance, vulnerability discovery, and exploit development, and evaluate new AI‑powered offensive techniques as they emerge
• Help define and mature DRW’s offensive security methodology, standards, and tooling, and mentor other engineers on the security team

Skills

Penetration testing

Red teaming

Scripting

Networking fundamentals

Cloud security

MITRE ATT&CK

Threat modeling

Reporting

Tools

Cobalt Strike

Metasploit

Burp Suite

Nmap

BloodHound

Job description

DRW in Chicago is seeking a Senior Offensive Security Engineer to lead red team engagements, perform penetration tests, and simulate adversaries across trading systems, corporate IT, and cloud platforms. You will act as a trusted adversary to identify weaknesses before attackers do.

You will translate findings into actionable improvements, help shape DRW's offensive security roadmap, and collaborate with security, infrastructure, and trading teams.