Lead Associate Principal, Adversarial Red Team

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 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 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), common enterprise infrastructure technology stacks, and network configurations. Ability to understand and probe/exploit a diverse range of Network and Internet Protocols, and to understand and modify code across multiple programming languages and frameworks, with direct 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. 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‑using 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. 7+ Years’ experience of Penetration testing. 7+ 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. 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. 401k 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. If hired at OCC, your final base salary compensation will be determined by factors such as skills, experience and/or education. In addition, we believe in the importance of pay equity and consider internal equity of our current team members as part of any final offer. We typically do not hire at the maximum of the range in order to allow for future and continued salary growth. We also offer a substantial benefits package as noted on All employees may be eligible for a discretionary bonus. Discretionary bonuses are based on various factors, including, but not limited to, company and individual performance and are not guaranteed. Salary Range $142,900.00 - $228,800.00 Incentive Range 8% to 15% OCC is an Equal Opportunity Employer. #J-18808-Ljbffr The Options Clearing Corporation (OCC)