Lead Penetration Tester
About The Role 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.
What You'll Do
- 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
Must-Have Who You Are
- 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