Lead Associate Principal, Adversarial Red Team

* THIS POSITION IS NOT ELIGIBLE FOR VISA SPONSORSHIP
* To be considered for this position, applications and resumes are accepted only through our careers site by directly applying to the posted job. We do not accept unsolicited resumes or sales solicitations from staffing agencies. Any OCC employee wishing to submit a referral must do so through their Workday account. Any resume submitted outside of an active job posting will not be considered for employment.

What You'll Do:

The Adversarial Red Team Lead Associate Principal provides professional input to complex Red Team assignments and projects, strengthening OCC's security posture by independently conducting covert black-box and occasional white-box assessments across network, web application, cloud, mobile, physical, and social engineering domains, while coordinating with Security and IT teams to address and retest remediated findings. This individual works independently and reviews or guides the work of more junior Red Team professionals, enhancing the knowledge and skill base of the organization.

Ideal candidates will bring 7+ years of deep expertise in areas such as OSINT, penetration testing, C2 infrastructure development, evasion techniques, and custom scripting, along with strong communication skills and a commitment to staying ahead of emerging threats. All team members are held to the highest standards of ethics, integrity, and accountability, and are expected to foster a collaborative, bar-raising dynamic with OCC's defensive security teams.

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 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, enhancing the knowledge and skill base of the organization.

* 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 while fostering a collaborative team environment.

* Perform other duties as assigned.

Supervisory Responsibilities:

* None

Qualifications:

The requirements listed are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the primary functions.

* High energy, results-driven, with strong analytical, problem-solving, and tactical planning skills, and the ability to exercise good judgment while developing creative solutions to long-term strategic goals.

* Exceptional verbal/written communication and listening skills, with strong enthusiasm for staying current on threat intelligence and emerging adversarial TTPs.

* Broad expertise across Network/Application, Web Application, and Mobile Application Penetration Testing, Command and Control (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 across reconnaissance, exploit/payload development, tooling, and findings triage.

* Proven due diligence and research ability via open-source avenues and technology.

* Strong familiarity with enterprise technologies; strong technical background and understanding of security-related technologies; prefer operational experience as an administrator, engineer, or developer and direct experience testing in commercial cloud environments (AWS, Azure, IaaS/PaaS/SaaS).

* Good applicable knowledge of policy and procedure development, systems analysis, IA policy, vulnerability and risk management, and regulatory standards (e.g., CSF, NIST, PCI, FIPS 199, COBIT
5).

* Strong knowledge of cryptography (symmetric, asymmetric, hashing),…