Job Title: Senior / Lead AI-Enabled Penetration TesterLocation: [Insert Location / Remote / Hybrid]
Department: Offensive Security / Cyber Security
Position Overview
Employment Type: Full-Time Senior / Lead AI-Enabled Penetration Tester to lead and execute advanced offensive security assessments across AI-enabled platforms, cloud environments, and enterprise infrastructure. In this role, you will specialize in cutting-edge security testing for GenAI/LLM-based applications, SaaS platforms, and multi-cloud environments (with a mandatory focus on GCP). You will bridge the gap between traditional web/cloud penetration testing and modern AI security, driving adversarial simulations, building custom automation, and mentoring junior testers to elevate our collective defensive posture.
Key Responsibilities AI & LLM Security Testing
- Assess GenAI Ecosystems: Conduct comprehensive security testing of GenAI/LLM-based applications, AI models, autonomous agents, and APIs.
- Apply AI Frameworks: Leverage the OWASP LLM Top 10 and emerging AI security frameworks to mitigate model-specific risks (e.g., prompt injection, data poisoning).
SaaS, Cloud & Red Teaming
- SaaS Penetration Testing: Perform deep-dive web application testing on cloud-native SaaS platforms to expose complex business logic flaws and vulnerabilities.
- GCP & Multi-Cloud Exploitation: Assess cloud security controls, configurations, and attack paths specifically across GCP (mandatory), with secondary exposure to AWS and Azure.
- Adversary Simulation: Execute red team engagements and attack emulation exercises to evaluate organizational resilience against real-world threats.
Tooling, Automation & DevSecOps
- Custom Tool Development: Write and deploy custom scripts and offensive tooling using Python, PowerShell, and Bash.
- Secure SDLC Integration: Collaborate with DevSecOps and cloud teams to embed remediation recommendations directly into the Secure Software Development Lifecycle.
- Architecture Review: Review authentication (IAM), cryptographic implementations, network controls, Kubernetes/Docker environments, and Infrastructure-as-Code (IaC) deployments.
Leadership & Strategy
- Methodology Innovation: Drive continuous refinement of internal penetration testing playbooks, automation capabilities, and AI-focused security assessment practices.
- Mentorship: Act as a technical mentor to junior security testers and champion offensive security best practices.
What You'll Need (Required Qualifications)
- Education: Bachelor's degree in Computer Science, Cyber Security, IT, or a related field (preferred but equivalent experience valued).
- Experience: 7 to 10 years of hands-on experience in Penetration Testing, Offensive Security, Red Teaming, and Vulnerability Assessments.
- AI Security Domain: Proven track record testing AI/LLM applications against the OWASP LLM Top 10 framework.
- Cloud Core: Deep engineering-level understanding of GCP (IAM, networking, logging, storage, and compute).
- Programming Skills: Strong proficiency in Python, PowerShell, and Bash for building custom offensive security tools.
- AppSec & Methodology: Thorough understanding of the standard OWASP Top 10, API vulnerabilities, cryptography, and experience with AppSec tooling (SAST, DAST, SCA, threat modeling).
- Soft Skills: Excellent report-writing and communication skills; ability to articulate highly technical risks to business stakeholders.
- Certifications (Highly Desirable): OSCP, OSWE, CRTO, GPEN, GWAPT, CISSP, or advanced GCP/Cloud Security certifications.
- Flexibility: Ability to manage multiple client-facing projects simultaneously and support occasional after-hours critical testing or red team initiatives.
Nice-to-Haves (Preferred Skills)
- Container Security: Hands-on experience with Kubernetes, Docker, and container escape testing techniques.
- Infrastructure-as-Code: Experience identifying misconfigurations in Terraform, CloudFormation, or ARM templates.
- Defensive Awareness: Familiarity with Digital Forensics, Incident Response (DFIR), WAF bypasses, and Zero Trust architectures.
- Enterprise Controls: Knowledge of CSPM/CNAPP platforms and compliance frameworks (SAMM, ISO 27001, NIST CSF).
- Thought Leadership: Prior experience leading complex technical engagements and public/internal research contributions.