Deep Technical Red Teaming and Penetration Testing Specialist

We are seeking an experienced and highly technical freelancer to conduct an advanced Red Teaming and Penetration Testing engagement. This project is for someone deeply skilled in offensive operations, with a strong focus on realistic, low-level attack techniques that mimic real-world adversaries. What We're Looking For: Red Teaming Expertise: Proven ability to execute realistic attack simulations, including persistence, stealth, and evasion. You must be capable of gaining and maintaining undetected access in a manner similar to well-resourced threat actors. Your role will involve using techniques that go beyond typical vulnerability scanning, with a focus on exploiting deep, systemic weaknesses. In-Depth Technical Knowledge: Mastery of network protocols, Active Directory exploitation, privilege escalation, lateral movement, and Command & Control (C2). Strong experience in exploiting vulnerabilities in Windows, Linux, cloud systems, and other complex environments. Ability to exploit and chain vulnerabilities to achieve meaningful attack objectives. Tools and Techniques: Expert-level use of tools like Cobalt Strike, Metasploit, Mimikatz, Responder, BloodHound, Empire, and others. You must also be comfortable using Living off the Land techniques (LOLBins) and custom scripts to exploit misconfigurations or weaknesses. Experience with bypassing modern security measures, such as EDR evasion, is critical. Advanced Attack Skills: Hands-on experience with protocol exploitation, packet crafting, reverse engineering, and custom payload development. You should be comfortable developing your own exploits, adapting public techniques to fit specific scenarios, and evading advanced detection mechanisms. Familiarity with kernel-level exploits and deep system manipulation is a plus. Realistic Threat Actor Simulation: Proficiency in executing multi-stage, highly targeted attacks (e.g., phishing, lateral movement, persistence). Familiarity with MITRE ATT&CK Framework and a deep understanding of how sophisticated threat actors operate, including their tactics, techniques, and procedures (TTPs). Project Overview: Objective: To identify and exploit real vulnerabilities within our security environment, and provide actionable insights for remediation. The goal is not only to uncover weaknesses but to simulate a real-world adversary, showing how an attacker would move laterally, establish persistence, and exfiltrate data. Scope: Conduct both internal and external penetration tests, including black-box and white-box scenarios, with emphasis on sophisticated attack chains that involve multiple vectors. Expect to use every technique available—from phishing and social engineering to advanced evasion tactics, Active Directory attacks, and persistence mechanisms. Live Assessment: Applicants will be provided with an isolated, hardened test environment and must successfully breach it as part of the selection process. The assessment will include initial compromise (e.g., phishing or exploitation), lateral movement, and demonstrating persistence techniques that mirror the actions of sophisticated adversaries. Timeline: Estimated at 4-6 weeks, depending on the complexity of findings and the depth of analysis required. Deliverables: A highly technical report detailing findings, including all attack paths, persistence mechanisms, remediation recommendations, and strategic improvements for enhancing security posture. The report must include both technical depth and executive-level summaries for non-technical stakeholders. Desired Qualifications: Strong Offensive Security Background: Demonstrated success in conducting Red Team operations and penetration tests with a focus on high-value targets or critical infrastructure. The candidate should have experience with engagements that mimic nation-state or advanced criminal actor methodologies. Low-Level, Deep Technical Understanding: Comfort working at the packet and process level, creating custom exploits, modifying malware, analyzing protocol behavior, and executing living-off-the-land strategies. You must be able to identify and exploit opportunities that traditional security testing would miss. Practical Engagement Experience: Must have extensive experience in real-world engagements where gaining and maintaining unauthorized access was critical. This includes familiarity with post-exploitation activities and long-term stealth tactics. Clear Reporting Skills: Ability to document and communicate findings clearly and accurately, making complex technical issues understandable for both technical and non-technical audiences, including C-level executives. Professionalism and Integrity: Absolute adherence to ethical hacking principles, security best practices, and maintaining client confidentiality at all times. Experience handling sensitive information and working under strict NDAs is essential. How to Apply: If you are interested, please provide a summary of your experience, links to relevant case studies or previous engagements, and your rate. Please note that only applicants who successfully complete the live assessment will be considered for the role.