Lead Penetration Tester

Alignerr Corp.; Seattle (WA); Remote; USD 124,000 - 207,000; Full time

Benefits offered by this job

Fully remote

Freelance autonomy

Challenging targets

Ongoing engagements

Contract work opportunities

Job summary

Alignerr Corp. in Seattle is seeking a Lead Penetration Tester for fully remote, contract engagements across web, network, and cloud environments. You will design and execute offensive security tests, emulate attacker techniques, and deliver results to stakeholders.

You will produce structured reports with actionable remediation guidance and collaborate with red-team and purple-team efforts to strengthen defenses. This role rewards autonomy and ongoing contract opportunities.

Qualifications

• Background in offensive security, penetration testing, or red teaming.
• Hands-on experience with 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.

Responsibilities

• 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

Skills

Penetration testing

Red team

Report writing

Offensive security

Education

OSCP/OSWE/OSEP or similar certifications

Tools

Metasploit

Burp Suite

Cobalt Strike

Job description

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.

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