Lead Penetration Tester

* Plan and execute penetration tests across web applications, internal and external networks, and cloud infrastructure * Identify, validate, and exploit vulnerabilities to demonstrate real-world impact * Conduct post-exploitation analysis to assess the full scope and blast radius of discovered weaknesses * Deliver clear, structured technical reports with actionable severity assessments and remediation guidance * Challenge and validate defensive assumptions — test detection logic, not just defenses * Support recurring red-team and purple-team engagements alongside security operations teams

Who You Are

Must-Have: * Proven background in offensive security, penetration testing, or red teaming * Hands-on experience with common exploitation frameworks, tools, and methodologies (Metasploit, Burp Suite, Cobalt Strike, or similar) * Strong ability to think like an adversary and replicate real-world attack chains * Skilled at writing structured, professional technical reports that non-technical stakeholders can act on * Self-directed and reliable — you can manage engagements independently without hand-holding

Nice to Have: * Offensive security certifications (OSCP, OSWE, OSEP, CRTO, or similar) * Experience with cloud-specific attack paths (AWS, Azure, GCP) * Background in red team operations, adversary simulation, or threat emulation * Familiarity with purple team collaboration and detection engineering workflows

Why Join Us

* Fully remote — work from wherever you do your best work * Freelance autonomy with consistent, substantive engagements * Work on technically challenging targets across diverse environments * Contribute findings that directly improve real-world security posture * Potential for ongoing contract work and expanded engagements over time