Lead Penetration Tester

Offensive security engagements

Assess applications, internal and external networks, and cloud infrastructure through structured penetration testing. Work examines vulnerabilities and the defensive assumptions surrounding them.

• Plan and execute tests, validate weaknesses, and demonstrate their practical impact.
• Analyze post-exploitation conditions to understand the reach of identified vulnerabilities.
• Write technical reports with clear severity judgments and remediation advice.
• Challenge detection logic as well as protective controls.
• Support recurring red-team and purple-team exercises with security operations colleagues.

Required experience

You need a demonstrated background in penetration testing, offensive security, or red teaming. Practical familiarity with methods and tools such as Metasploit, Burp Suite, Cobalt Strike, or equivalents is essential.

The role requires the ability to model realistic attacker behavior and connect actions into plausible attack chains. Reports must be professional, organized, and useful to nontechnical stakeholders, while engagements require reliable independent management.

Helpful background

Certifications such as OSCP, OSWE, OSEP, or CRTO are useful. Cloud attack-path knowledge for AWS, Azure, or GCP, adversary simulation, threat emulation, purple-team collaboration, and detection engineering are also relevant.

Terms

This remote freelance contract involves substantive assessments across varied technical environments. Further contract work or expanded engagements may become available over time.