Cyber Assessment Manager (Penetration Testing)

About the role

KPMG Jamaica is seeking a Cyber Assessment Manager to lead offensive security initiatives, including penetration testing, red teaming, and AI‑focused threat simulations. You will work closely with security operations and development teams to identify, exploit, and remediate vulnerabilities across network, web, and cloud environments.

Key responsibilities

• Lead comprehensive network and web‑application penetration tests and assess infrastructure risk.
• Conduct red‑team exercises that emulate real‑world attacks and evaluate detection and response capabilities.
• Drive AI red‑team projects to uncover vulnerabilities in machine‑learning models (e.g., prompt injection, data poisoning, model evasion).
• Manage end‑to‑end vulnerability remediation, coordinating with technical teams for timely mitigation.
• Stay current on emerging threats, threat intelligence, and offensive techniques.
• Mentor junior team members and support their professional development.

Required profile

• Bachelor’s degree in Computer Science, Cybersecurity, or a related field.
• Minimum five years of hands‑on experience in penetration testing, red teaming, and cloud security assessments.
• Strong communication, analytical, and independent‑judgement skills.

Required skills

• Network, web‑application, and cloud penetration testing.
• Red teaming and AI red teaming (adversarial ML techniques).
• Familiarity with MITRE ATT&CK, MITRE ATLAS, OWASP, PTES, and NIST frameworks.
• Certifications such as GPEN, OSCP, OSCE, CISSP (preferred); Azure certifications a plus.
• Scripting/automation with Python, Bash, or PowerShell.
• Experience with adversarial machine‑learning tools and common security scanning utilities.