Assessments & Exercises Lead - Penetration Testing

As an Assessments & Exercises Lead in the Cyber and Tech Controls line of business, you will contribute significantly to enhancing the firm's cybersecurity posture by using industry-standard assessment methodologies and techniques to proactively identify risks and vulnerabilities in people, processes, and technology. Design and deploy risk-driven tests and simulations (or manage a highly-skilled team that does) and inform analysis to clearly outline root-causes. In this role, you will evaluate preventative controls, incident response processes, and detection capabilities, and advise cross-functional teams on security strategy and risk management.

Job responsibilities

• Design and execute testing and simulations – such as penetration tests, adversary emulation assessments, collaborative technical controls assessments, and cyber exercises, and contribute to the development and refinement of assessment methodologies, tools, and frameworks to ensure alignment with the firm’s strategy and compliance with regulatory requirements
• Evaluate controls for effectiveness and impact on operational risk, as well as opportunities to automate control evaluation
• Collaborate closely with cross-functional teams to develop comprehensive assessment reports – including detailed findings, risk assessments, and remediation recommendations – making data-driven decisions that encourage continuous improvement
• Utilize threat intelligence and security research to stay informed about emerging threats, vulnerabilities, industry best practices, and regulations. Apply this knowledge to enhance the firm's assessment strategy and risk management. Engage with peers and industry groups that share threat intelligence analytics

Required qualifications, capabilities, and skills

• 5+ years of experience in cybersecurity, with demonstrated exceptional organizational skills to plan, design, and coordinate the development of offensive security testing, assessments, or simulation exercises
• Knowledge of US financial services sector cybersecurity organization practices, operations risk management processes, principles, regulations, threats, risks, and incident response methodologies
• Ability to identify systemic security issues as they relate to threats, vulnerabilities, or risks, with a focus on recommendations for enhancements or remediation, and proficiency in multiple security assessment methodologies (e.g., Open Worldwide Application Security Project (OWASP) Top Ten, National Institute of Standards and Technology (NIST) Cybersecurity Framework) and offensive security testing tools
• Excellent communication, collaboration, and report writing skills, with the ability to document and explain complex technical details in a concise, understandable manner to individuals with a variety of both technical and non-technical backgrounds
• Strong understanding of the following: Windows/Linux/Unix/Mac operating systems; OS and software vulnerability and exploitation techniques; commercial or open-source offensive security tools for reconnaissance, scanning, exploitation, and post exploitation (e.g. Cobalt Strike, Metasploit, Burp Suite); networking fundamentals (all OSI layers, protocols); Infrastructure as a Service (IaaS) and Platform as a Service (PaaS) providers in both private and public (AWS, Azure) environments; DevOps; incident response; threat hunting; and familiarity with interpreting log output from networking devices, operating systems, and infrastructure services
• Manual penetration testing and assessments experience (beyond running automated tools) against a wide variety of applications including web, mobile, and thick clients, internal and external facing infrastructures

Preferred qualifications, capabilities, and skills

• Hold relevant industry certifications – such as Certified Information Systems Security Professional (CISSP), Certified Information Security Manager (CISM), or those offered by Offensive Security (OSCP, OSEP, OSED, OSEE, OSCE), CREST (Certified Simulated Attack Specialist, Registered Penetration Tester, Certified Infrastructure Tester), or SANS (GPEN, GXPN, GWAPT) – showcasing advanced expertise in cybersecurity and offensive testing methodologies
• Technical knowledge or experience developing proof of concept exploits and in house scripting, using interpreted languages such as Python, Ruby, or Perl, compiled languages such as C, C++, C#, or Java, and security tools or technology such as Firewalls, IDS/IPS, Web Proxies, DLP
• Intelligence Community/Security Services background, knowledge of malware packing, obfuscation, persistence, exfiltration techniques, and understanding of financial sector or other large security and IT infrastructures
• Experience querying log sources within large centralized logging platforms, e.g. Splunk, Elastic, Cloudera