Associate Principal, Adversarial Red Team

What You'll Do The Adversarial Red Team Associate Principal is responsible for strengthening OCC's security posture by 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. Ideal candidates will bring deep expertise in 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 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. 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. Supervisory Responsibilities None Qualifications High energy, results‑driven person with an attention to detail. Strong enthusiasm to stay up-to-date on Threat Intelligence and learn new adversarial TTPs to simulate on a regular basis. Exceptional analytical, problem‑solving and troubleshooting skills with the ability to exercise good judgment while developing creative solutions. Exceptional tactical planning skills based on long‑term strategic goals. Exceptional verbal/written communication skills to articulate ideas clearly and concisely. Excellent listening skills. Excellent focused domain areas of expertise as well as breadth across Network/Application Penetration Testing, Web Application Penetration Testing, Mobile Application Penetration Testing, Command and Control (C2) Infrastructure Development, Cyber Defense Evasion techniques, Social Engineering, Open‑Source Intelligence, Basic Emissions Testing, Physical Security Testing, and more. Strong working knowledge of Artificial Intelligence (AI) large language models (LLMs) and agentic AI systems – including autonomous and tool‑using agents, orchestration frameworks, and protocols like Model Context Protocol (MCP) – and ability to evaluate how these technologies can accelerate offensive security tradecraft across reconnaissance, exploit, payload development, adversarial tooling, and triaging for security findings. Proven due diligence and research ability via open‑source avenues and technology. Strong familiarity with enterprise technologies; experience as an administrator, engineer, or developer and direct experience testing in commercial cloud environments (AWS, Azure, IaaS/PaaS/SaaS). Good knowledge of policy and procedure development, systems analysis, Information Assurance (IA) policy, vulnerability management, and risk management. Good understanding of regulatory standards including CSF, NIST, PCI, SSAE 16, SAS 70, HIPAA, FIPS 199, COBIT 5 and others as needed. Strong knowledge of cryptography (symmetric, asymmetric, hashing) and its applications. Strong knowledge of common enterprise infrastructure technology stacks and network configurations. Ability to understand and probe/exploit a diverse range of Network and Internet Protocols. Ability to understand and modify code in diverse programming languages and frameworks; must have practical experience with one or more high‑level programming languages. Ability to facilitate meetings and conversations. Ability to work with business users, understand their needs and translate those needs to the final project deliverables. Nice to have experience working on critical infrastructure in a regulated environment. 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 and associated defense evasion techniques for behavioral‑based alerting. 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 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 of experience in penetration testing. 5+ years of experience in Information Assurance or Cybersecurity work environments. Certificates or Licenses Security‑related certifications (OSCP, OSWE, OSCE, GPEN, GXPN, GWAPT, ARTE, etc.) highly desired. Benefits 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. 401(k) employer match. Competitive health benefits including medical, dental and vision. Compensation The salary range listed for any given position is exclusive of fringe benefits and potential bonuses. The final base salary will be determined by factors such as skills, experience and/or education. We typically do not hire at the maximum of the range to allow for future and continued salary growth. A substantial benefits package is offered. All employees may be eligible for a discretionary bonus based on company and individual performance. Salary Range $121,900.00 – $197,100.00 Incentive Range 8% – 15% Equal Opportunity Statement OCC is an Equal Opportunity Employer. #J-18808-Ljbffr