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.

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