Penetration Tester

Penetration Tester 6 month contract to perm Fully Remote Duties Execute cloud security assessments across AWS Azure or GCP environments. Identify exploit and document vulnerabilities in a controlled and ethical manner. Validate remediation efforts through structured re-testing. Plan and execute adversary emulation exercises aligned with real-world threat actors. Simulate full attack lifecycles including initial access privilege escalation lateral movement persistence and data exfiltration. Conduct social engineering and phishing campaigns where authorized. Evaluate detection and response capabilities in collaboration with defensive teams. Develop and refine offensive tooling and techniques to emulate evolving threats. Utilize AI and LLM-based tools to enhance reconnaissance payload development and automation. Develop workflows integrating AI into penetration testing processes and Red team operations. Test for vulnerabilities including prompt injection jailbreak attempts model abuse and data leakage. Evaluate risks related to model extraction model inversion and training data poisoning. Assess Retrieval-Augmented Generation (RAG) implementations and AI plugin integrations. Contribute to AI threat modeling and secure deployment recommendations.

Qualifications

Bachelor’s degree in Cybersecurity Computer Science Information Technology or equivalent experience. 3–7+ years of experience in penetration testing red teaming or offensive security. Offensive security certifications (e.g. OSCP OSEP CRTO GPEN GWAPT). Experience testing AI or machine learning systems in production environments. Experience using AI tools to automate or enhance technical workflows. Understanding of AI/LLM architectures and common attack vectors against AI systems. Demonstrated experience conducting full-scope penetration tests and adversary simulations. Strong understanding of networking operating systems (Windows and Linux) Active Directory and web technologies. Experience with industry-standard tools such as Burp Suite Metasploit Nmap BloodHound and command-and-control frameworks. Proficiency in Python and scripting (Bash or PowerShell).