Lead Associate Principal, Adversarial Red Team

OCC

Adversarial Red Team lead strengthening OCC’s equity-derivatives clearing security. Conducting offensive assessments across networks, applications, cloud, mobile, physical, and social-engineering domains.

Posted 8/4/2026full-time🇺🇸 United StatesSenior💰 $142,900 - $228,800 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive expertise in penetration testing, including network, application, and cloud security, while leveraging AI/LLM tools for enhanced offensive research and threat modeling. Proficient in developing Command and Control (C2) infrastructure and conducting comprehensive security assessments aligned with regulatory standards.

Highest-signal resume keywords

Penetration TestingCommand and Control (C2) DevelopmentAI/LLM ToolingSecurity Risk AssessmentVulnerability Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Network Penetration TestingApplication Penetration TestingCloud Security TestingExploit DevelopmentThreat ModelingOSINTCryptographyCustom ScriptingDatabase Security TestingSecurity Controls Validation

Soft Skills

Analytical SkillsProblem-SolvingCommunication SkillsCollaborationLeadership

Tools & Technologies

KaliMetasploitCobalt StrikeNmapNessusBurp SuiteWiresharkCrowdStrikeCarbon BlackMicrosoft Office

Certifications & Qualifications

OSCPOSWEOSCEGPENGXPNGWAPT

Industry Keywords

CybersecurityInformation AssuranceRegulatory StandardsVulnerability ManagementCritical Infrastructure

Tech Stack

Tools & technologies

AWSAzureCloudCyber SecurityMacOSMySQLPythonUnix

About the role

Key responsibilities & impact

Execute comprehensive Red Team simulations covering 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, exploit development, and 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 security, network, and applications
Develop evidence-based reports with actionable remediation recommendations
Debrief stakeholders on findings
Ensure security controls and testing align with regulations, industry best practices, and OCC policies
Cross-train Red Team and Security/IT teams on adversarial threats, attack vectors, and remediation strategies
Monitor emerging threats, threat intelligence, and attack techniques, advising IT leadership on mitigation
Support audits and contribute to security roadmap development
Review or guide junior Red Team professionals
Foster collaboration with OCC’s defensive security teams
Perform other duties as assigned

Requirements

What you’ll need

7+ years of penetration testing experience
7+ years of experience in Information Assurance or Cybersecurity work environments
Broad expertise in network/application, web application, and mobile application penetration testing
Command and Control (C2) infrastructure development experience
Cyber Defense evasion techniques, social engineering, OSINT, basic emissions testing, and physical security testing
Strong working knowledge of AI/LLMs and agentic systems, including autonomous agents, orchestration frameworks, and MCP
Proven open-source research and due diligence ability
Strong familiarity with enterprise technologies and security-related technologies
Operational experience as an administrator, engineer, or developer preferred
Direct experience testing commercial cloud environments including AWS, Azure, IaaS, PaaS, and SaaS
Knowledge of policy and procedure development, systems analysis, IA policy, vulnerability and risk management, and regulatory standards including CSF, NIST, PCI, FIPS 199, and COBIT 5
Strong knowledge of cryptography, enterprise infrastructure technology stacks, and network configurations
Ability to understand and probe/exploit diverse network and Internet protocols
Ability to understand and modify code across multiple programming languages and frameworks, with practical experience in at least one high-level language
Ability to facilitate meetings and translate business needs into project deliverables
Security-related certifications such as OSCP, OSWE, OSCE, GPEN, GXPN, GWAPT, or ARTE highly desired
BS in Computer Science, Information Management, Information Security, or comparable technical degree is desired but not required
Strong proficiency in network, web application, cloud, and mobile device security testing
Exploit, payload, and attack framework development experience
Knowledge of EDR detection capabilities such as CrowdStrike and Carbon Black, and behavioral-alert defense evasion
Custom scripting and process automation experience using Python, PowerShell, Bash, or similar
Database security testing experience with MSSQL, DB2, MySQL, or similar
Proficiency with penetration testing tools including Kali, Metasploit, Cobalt Strike, Nmap, Nessus, Burp Suite, Wireshark, Hashcat, BloodHound, Ghidra, Mimikatz, Impacket, and others
Track record of vulnerability research and CVE assignments
Knowledge of Windows APIs and Living off the Land binaries
Experience with Mainframes, Windows, Unix, macOS, and Cisco platforms and controls
Proficiency with Microsoft Office and basic Microsoft SharePoint document management
High energy, results-driven approach with strong analytical, problem-solving, and tactical planning skills
Exceptional verbal, written communication, and listening skills
Ability to work independently and guide junior Red Team professionals
Experience with critical infrastructure in a regulated environment is a plus

Benefits

Comp & perks

A highly collaborative and supportive environment developed to encourage work-life balance and employee wellness
A hybrid work environment, up to 2 days per week of remote work
Tuition Reimbursement to support your continued education
Student Loan Repayment Assistance
Technology Stipend allowing you to use the device of your choice to connect to our network while working remotely
Generous PTO and Parental leave
401k Employer Match
Competitive health benefits including medical, dental and vision
Annual discretionary incentive compensation award, target range 8% to 15% (not guaranteed)