Lead Penetration Tester

What if your ability to think like an attacker could directly make organizations more secure? We're looking for a Lead Penetration Tester to conduct sophisticated offensive security engagements — probing applications, networks, and cloud environments for vulnerabilities before the real adversaries do.

This is a fully remote contract role built for experienced offensive security professionals who thrive on technical challenge, think creatively under pressure, and communicate findings with clarity and precision.

• 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

• 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

• 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

• 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