Senior Penetration Tester — Remote, End-to-End Security Testing

Trespass Security LLC; Northern (KY); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Trespass Security LLC is seeking a senior penetration tester to autonomously plan and execute tests on web apps, APIs, networks, and cloud environments with written authorization and defined engagement rules.

You will clarify scope, document findings, and communicate results to customers, including retesting eligible fixes, while maintaining strong reporting discipline and stakeholder communication.

Qualifications

• Senior-level experience independently planning and performing penetration tests within written authorization.
• Depth in web application and API testing, plus practical experience with network and cloud attack surfaces.
• Ability to validate findings, reason about realistic attack paths, and communicate technical impact without overstating it.
• Strong report writing and the ability to discuss findings with both technical teams and business stakeholders.
• Sound judgment around customer data, credentials, evidence, scope boundaries, escalation paths, and stop conditions.
• Relevant degrees and security certifications are welcome but are not required.

Responsibilities

• Own the work from context to retest.
• Perform and document testing across approved web, API, network, and cloud targets.
• Validate findings, preserve useful evidence, and distinguish verified findings from unconfirmed signals.
• Communicate through delivery: provide status updates, write reports, lead customer readouts, explain remediation direction, and complete eligible retests.

Skills

Penetration testing

Web application testing

API testing

Network testing

Cloud security testing

Job description

Trespass Security LLC is seeking a senior penetration tester to autonomously plan and execute tests on web apps, APIs, networks, and cloud environments with written authorization and defined engagement rules.

You will clarify scope, document findings, and communicate results to customers, including retesting eligible fixes, while maintaining strong reporting discipline and stakeholder communication.