Lead Penetration Tester

Lead Penetration Tester

About the Role

What if you could get paid to think like a hacker — probing systems, uncovering hidden vulnerabilities, and staying one step ahead of real-world adversaries? We're looking for an experienced Lead Penetration Tester to conduct deep offensive security engagements across applications, networks, and cloud environments.

This is a fully remote contract role built for security professionals who thrive at the intersection of creative thinking and technical precision. If you've spent your career finding what others miss, this is your kind of work.

What You'll Do

• Conduct end-to-end penetration tests across web applications, internal and external networks, and cloud infrastructure
• Identify, validate, and exploit vulnerabilities — then clearly articulate the real-world impact
• Perform post-exploitation analysis to demonstrate the full attack chain and business risk
• Produce high-quality, structured reports with severity ratings, evidence, and actionable remediation guidance
• Validate defensive assumptions and challenge detection logic to expose gaps before adversaries do
• Support red-team and purple-team engagements on a recurring basis
• Replicate adversary tactics, techniques, and procedures (TTPs) to stress-test defenses under realistic conditions

Who You Are

Must-Have:

• Solid background in offensive security, ethical hacking, or penetration testing
• Hands-on experience with common exploitation frameworks, tools, and methodologies (Metasploit, Burp Suite, Cobalt Strike, or similar)
• Ability to write clear, well-structured technical reports that communicate findings to both technical and non-technical audiences
• Strong understanding of attack vectors across application, network, and cloud layers
• Self-directed and reliable — you deliver quality work without needing hand-holding

Nice to Have:

• Offensive security certifications such as OSCP, OSWE, OSEP, CRTO, or equivalent
• Experience with red-team or purple-team operations
• Familiarity with cloud security testing (AWS, Azure, GCP)
• Background in threat modeling or adversary simulation

Why Join Us

• Work on high-impact security engagements that challenge your skills at every turn
• Fully remote and flexible — work on your own schedule from anywhere
• Freelance autonomy with the structure of meaningful, well-scoped engagements
• Hone your craft across a diverse range of environments, targets, and attack surfaces
• Potential for ongoing work and contract extension across new engagements