- Cyber Assessment Manager (Penetration Testing)
- KPMG Jamaica (JESS)
- Kingston and St. Andrew
- Not disclosed
- Permanent full-time
- Updated 24/07/2026
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In this role you will be responsible for simulating cyberattacks to proactively identify vulnerabilities in our systems, networks, and web applications, with a focus on AI system robustness assessments.
JOB SUMMARY:
In this role, you will focus on offensive security assessment work with a significant emphasis on penetration testing and red teaming. You will lead initiatives to discover, exploit, and analyze system vulnerabilities while collaborating with security operations and development teams to align with security objectives and risk mitigation goals. Your expertise in advanced penetration testing frameworks and emerging AI security practices will guide efforts to analyze and recommend robust security enhancements. You will manage vulnerability remediation lifecycles.
Key Responsibilities:
Lead comprehensive network and web application penetration tests to identify security vulnerabilities and assess organizational infrastructure risk
Conduct red teaming exercises to emulate real-world cyber threats and evaluate security operations detection and response capabilities
Engage in advanced AI Red Teaming initiatives to discover vulnerabilities and improve the overall security, safety, and robustness of artificial intelligence systems
Facilitate end-to-end security assessments and manage the remediation and resolution of identified vulnerabilities, collaborating with technical teams to ensure timely mitigation
Track and analyze the latest cybersecurity trends, threat intelligence, and offensive techniques to keep testing methodologies current and adaptive
Must-Have Skills and Experience:
- Bachelor's degree in Computer Science, Cybersecurity, or a related field
Minimum of five (5) years’ practical experience in cybersecurity, focusing on network and web application penetration testing, red teaming, AI red teaming, cloud penetration testing, and security assessments
Proficiency in network and cloud security concepts, with hands-on experience in cloud penetration testing, and strong understanding of network penetration testing is preferred
Strong familiarity with frameworks such as MITRE ATT&CK and MITRE ATLAS, OWASP, PTES, and NIST, with relevant certifications such as GPEN, OSCP, OSCE, CISSP, or similar are highly preferred; Certifications in Azure a plus
- Proficiency in scripting and automation with experience in Python, Bash, or PowerShell
Experience with adversarial machine learning techniques and familiarity with common ML frameworks and tools. (prompt injection, data poisoning, and model evasion)
Special Conditions:
Expected to work in a fast-paced team environment.
Will be working primarily in a paperless environment and expected to use information systems for the entire workday to access data or perform activities.
May be required to work extended hours periodically or on public holidays.
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Are you skilled in penetration testing, red teaming, and AI security? Join KPMG Jamaica Extended Support Services (JESS) as a Cybersecurity Penetration Tester and help strengthen our systems against evolving threats. If you're ready to make an impact in a collaborative and innovative environment—apply today!
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- Cyber Assessment Manager (Penetration Testing)
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Learn more about JESS here:
- K-JESS Homepage
© 2026 KPMG Jamaica Extended Support Services Limited, a company incorporated in Jamaica and a member firm of the KPMG global organization of independent member firms affiliated with KPMG International Limited, a private English company limited by guarantee. All rights reserved.
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