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Associate Principal, Adversarial Red Team

Chicago - 125 S Franklin💼 Full-time🗓 2026-07-02 → 2026-09-26

Core

Conduct covert black-box and white-box security assessments across network, web application, cloud, mobile, physical, and social engineering domains to strengthen organizational security posture.

Role type

Associate Principal Adversarial Red Teamer

Builds

Offensive security simulations, C2 infrastructure, and threat intelligence for defensive teams

Domain

Cybersecurity / Offensive Security / Adversarial Operations

Deliverable

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

Required skills

Penetration testing, C2 infrastructure development, evasion techniques, custom scripting, OSINT, threat modeling, security risk assessment, AI/LLM tooling for offensive research, cryptography, network protocol exploitation, exploit development, social engineering, physical security testing, mobile security testing, cloud security testing, database security testing, vulnerability research, CVE assignment, Living off the Land (LOL) binaries, mainframe/Unix/Windows/MacOS platform testing

Preferred skills

Experience in regulated environments, knowledge of policy/procedure development, familiarity with EDR detection capabilities, experience with dedicated document management tools, ServiceNow usage

Technologies

Python, Powershell, Bash, AWS, Azure, Kali, Metasploit, Cobalt Strike, Nmap, Burp Suite, Wireshark, Ghidra, Sublist3r, Rubeus, Mimikatz, CrackMapExec, Exploitdb, Yersinia, Impacket, MSSQL, DB2, MySQL, Microsoft Office, SharePoint, ServiceNow, Model Context Protocol (MCP)

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; Support audits and contribute to security roadmap development

Seniority

Senior, hands-on IC

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