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Lead Associate Principal, Adversarial Red Team

Chicago - 125 S Franklin💼 Full-time💰 $142,900–$142,900🗓 2026-07-02 → 2026-07-31

Core

Lead Associate Principal conducting covert black-box and white-box adversarial Red Team assessments to strengthen OCC's security posture across network, web, cloud, mobile, physical, and social engineering domains.

Role type

Senior IC Adversarial Red Team Lead

Builds

Offensive security simulations, C2 infrastructure, exploit frameworks, and threat intelligence for a financial market utility.

Domain

Cybersecurity / Financial Services

Deliverable

production ML models | product features | dashboards & analysis | research | client delivery | infrastructure | physical/clinical work

Required skills

Penetration testing, C2 infrastructure development, evasion techniques, OSINT, AI/LLM tooling for offensive research, custom scripting, threat modeling, cryptography, network protocol exploitation, code modification across multiple languages

Preferred skills

Experience testing in commercial cloud environments (AWS, Azure), knowledge of EDR detection capabilities and evasion, vulnerability research and CVE assignments, experience with Mainframes/Unix/MacOS/Cisco, experience with ServiceNow and DMS tools

Technologies

Python, Powershell, Bash, Kali, Metasploit, Cobalt Strike, Nmap, Burp Suite, Wireshark, Ghidra, Sublist3r, Rubeus, Mimikatz, CrackMapExec, AWS, Azure, MSSQL, DB2, MySQL, Windows APIs, LOL Binaries

Responsibilities

Execute comprehensive Red Team simulations including network/application penetration testing, cloud security, social engineering, physical security, mobile testing, and OSINT; Develop and deploy Command and Control (C2) infrastructure using evasion and obfuscation techniques; Leverage AI/LLM tooling to accelerate offensive research and exploit development; Conduct ad-hoc white-box testing and validate remediated findings; Perform threat modeling, security risk assessments, and independent reviews; Develop clear, evidence-based reports with actionable remediation recommendations; Cross-train Red Team members and other Security/IT teams on adversarial threats; Stay current on emerging threats and advise IT leadership on mitigation approaches

Seniority

Senior, hands-on IC with mentorship responsibilities

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