Penetration Tester

Job Title #1: Associate Principal, Adversarial Red Team

Location: Chicago, IL (Onsite – Hybrid - 3 days in a week)

Position Type: Fulltime permanent position

Responsibilities:

Primary Duties and Responsibilities:

• To perform this job successfully, an individual must be able to perform each primary duty satisfactorily.
• Execute comprehensive Red Team simulations including network/application penetration testing, cloud security, social engineering, physical security, mobile testing, and OSINT within defined rules of engagement.
• Develop and deploy Command and Control (C2) infrastructure using evasion and obfuscation techniques to test and enhance Cyber Defense detection capabilities.
• Leverage AI/LLM tooling to accelerate offensive research, exploit development, and overall Red Team effectiveness.
• Conduct ad-hoc white-box testing on pre-production and in-development infrastructure, and validate remediated findings with IT owners.
• Perform threat modeling, security risk assessments, and independent reviews of CLIENT’S's security, network, and applications.
• Develop clear, evidence-based reports with actionable remediation recommendations and debrief stakeholders on findings.
• Ensure security controls and testing activities align with applicable regulations, industry best practices, and CLIENT’S policies and procedures.
• Cross-train Red Team members and other Security/IT teams on adversarial threats, attack vectors, and remediation strategies.
• Stay current on emerging threats, threat intelligence, and attack techniques, advising IT leadership on mitigation approaches.
• Support audits, contribute to security roadmap development, and mentor team members while fostering a collaborative team environment.
• Perform other duties as assigned.

Technical Skills:

• Strong proficiency in Network, Web Application, Cloud, and Mobile Device security testing
• Demonstrated exploit, payload, and attack framework development experience
• Strong knowledge of EDR detection capabilities such as Crowdstrike/Carbon Black, etc. and associated defense evasion techniques for behavioral based alerting
• Strong working knowledge of Artificial Intelligence (AI) large language models (LLMs) and agentic AI systems – including how autonomous and tool-usig agents, orchestration frameworks, and protocols like Model Context Protocol (MCP) operate – and the ability to evaluate how these technologies can accelerate offensive security tradecraft across reconnaissance, exploit and payload development, adversarial tooling development, and enhance triaging for security findings.
• Strong proficiency in social engineering and intelligence gathering.
• Strong experience with custom scripting (Python, Powershell, Bash, etc.) and process automation.
• Strong experience with database security testing (MSSQL, DB2, MySQL, etc.).
• Strong proficiency with common penetration testing tools (Kali, Armitage, Metasploit, Cobalt Strike, Nighthawk, Nmap, Qualys, Nessus, Burp Suite, Wireshark, Recon-NG, Ettercap/Bettercap, Hashcat, Bloodhound, Ida Pro, Ghidra, Sublist3r, Rubeus, Mimikatz, CrackMapExec, Exploitdb, Yersinia, Impacket, etc.).
• Track record of vulnerability research and CVE assignments
• Knowledge of Windows APIs and Living off the Land (LOL) Binaries
• Experience with Mainframes, Windows, Unix, MacOS, Cisco, platforms and controls.
• Proficient in creating content with Microsoft Office (Word, Excel, PowerPoint, Visio).
• Proficient in basic document management in a Microsoft SharePoint environment.
• Experience with dedicated document management tools (e.g., DMS, PolicyTech) is a plus.
• Experience with using ServiceNow is a plus.

Education and/or Experience:

• BS in Computer Science, Information Management, Information Security or other comparable technical degree from an accredited college/university is desired but not required
• 3+ Years’ experience of Penetration testing
• 5+ Years’ experience in Information Assurance or Cybersecurity work environments

Certificates or Licenses:

• Security-related certifications (OSCP, OSWE, OSCE, GPEN, GXPN, GWAPT, ARTE, etc.) highly desired.