Penetration Tester / Red Team Operator (AI-Focus)

Penetration Tester / Red Team Operator (AI-Focus)
100% Remote W2 Contract Role
6 Months Contract-to-Hire
Interviews: 2 or 3 rounds

Must be authorized to work in the U.S. without current or future employer sponsorship.

Position Overview
Penetration Tester / Red Team Operator (AI-Focus)
We are seeking a highly skilled Penetration Tester and Red Team Operator with a strong focus on AI-enabled security testing. This role combines traditional offensive security testing with advanced adversary simulation and AI system security assessment.

The successful candidate will leverage artificial intelligence tools to enhance penetration testing methodologies while also assessing the security and robustness of AI-driven applications, including large language models (LLMs) and machine learning systems. This position requires a strong technical foundation, an adversarial mindset, and the ability to communicate risk effectively to both technical and non-technical stakeholders.

Key Roles & Responsibilities:
Penetration Testing
• Conduct internal and external network penetration tests.
• Perform web application and API security assessments.
• 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.
• Produce comprehensive technical reports and executive-level summaries.
• Collaborate with stakeholders to define the objectives and scope of testing.

Red Team Operator
• 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.

AI-Enhanced Offensive Security
• 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.
• Evaluate the effectiveness and limitations of AI tools in offensive security operations.
• Continuously assess emerging AI technologies for potential security applications.

AI / Machine Learning Security Testing
• Conduct security assessments of AI-powered applications and services.
• 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.

Research and Development
• Stay current with emerging threats, vulnerabilities, and offensive security methodologies.
• Contribute to the development of internal tools, scripts, and red team frameworks.
• Maintain knowledge of industry standards such as MITRE ATT&CK and OWASP (including AI-focused frameworks).
• Support continuous improvement of offensive security methodologies.

Required 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.
• 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).

Preferred Qualifications
• Offensive security certifications (e.g., OSCP, OSEP, CRTO, GPEN, GWAPT).
• Experience testing AI or machine learning systems in production environments.
• Knowledge of secure software development practices.
• Experience in cloud-native environments and containerized systems.
• Prior experience contributing to open-source security tools or research publications.

Core Competencies
• Strong analytical and problem-solving skills.
• Adversarial and creative thinking mindset.
• Excellent written and verbal communication skills.
• Ability to present technical findings to executive leadership.
• High ethical standards and professional integrity.
• Ability to manage multiple projects and deadlines effectively.