Lead Associate Principal, Adversarial Red Team

Adversarial Red Team Lead Associate Principal

• 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, validate remediated findings with IT owners.
• Perform threat modeling, security risk assessments, and independent reviews of OCC’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 OCC 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 review or guide the work of more junior Red Team professionals.
• Perform other duties as assigned.

• 7+ years of deep expertise in OSINT, penetration testing, C2 infrastructure development, evasion techniques, and custom scripting.
• Strong communication skills and a commitment to staying ahead of emerging threats.
• Broad expertise across Network/Application, Web Application, Mobile Application penetration testing, C2 infrastructure development, Cyber Defense evasion techniques, Social Engineering, OSINT, Basic Emissions Testing, and Physical Security Testing.
• Strong working knowledge of AI/LLMs and agentic systems (autonomous agents, orchestration frameworks, MCP) and how they can accelerate offensive security tradecraft.
• Proven due diligence and research ability via open-source avenues and technology.
• Strong familiarity with enterprise technologies; experience testing in commercial cloud environments (AWS, Azure, IaaS, PaaS, SaaS).
• Good knowledge of policy and procedure development, systems analysis, IA policy, vulnerability and risk management, and regulatory standards (CSF, NIST, PCI, FIPS 199, COBIT
  5).
• Strong knowledge of cryptography (symmetric, asymmetric, hashing), common enterprise infrastructure technology stacks, and network configurations.
• Ability to understand and probe/exploit a diverse range of Network and Internet Protocols, and to modify code across multiple programming languages and frameworks, with practical experience in at least one high-level language.
• Ability to facilitate meetings and conversations, and to work with business users to translate their needs into final project deliverables.
• Nice to have: experience working on critical infrastructure in a regulated environment.

• 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/Cobalt Black and associated defense evasion techniques.
• Strong proficiency in social engineering and intelligence gathering.
• Strong experience with custom scripting (Python, Power Shell, Bash, etc.) and process automation.
• Strong experience with database security testing (MSSQL, DB2, MySQL, etc.).
• 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, Crack Map Exec , 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…