Senior Penetration Tester

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

Own authorized penetration tests from scoping input through careful investigation, clear reporting, customer review, and retesting.

The role

You will independently test web applications, APIs, networks, and cloud environments within written authorization and defined Rules of Engagement.

You will help clarify scope, keep customers informed, investigate and validate findings, write useful reports, discuss results, and retest eligible fixes. The work requires technical depth and the judgment to explain what the evidence does—and does not—show.

What you will do

Own the work from context to retest.

Review the business requirement and technical context, identify open questions, and provide practical scoping input before testing begins.

Perform and document testing

Conduct manual, evidence-driven testing across approved web, API, network, and cloud targets while respecting restrictions and stop conditions.

Validate findings

Investigate potential weaknesses, confirm relevant impact, preserve useful evidence, and distinguish verified findings from unconfirmed signals.

Communicate through delivery

Provide clear status updates, write reports, lead customer readouts, explain remediation direction, and complete eligible retests.

What we are looking for

Demonstrated ability matters more than a particular credential.

• 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.

What success looks like

Engagements move from scope to retest without losing technical clarity.

• Testing covers the authorized targets and important attack paths without crossing documented boundaries.
• Potential findings are investigated, supported by useful evidence, and written without overstating impact.
• Customers understand the findings, limitations, remediation direction, and next steps.
• Eligible fixes are retested against the original finding and documented clearly.

Employment, location, and authorization.

Employment and location

This is full-time W-2 employment and is fully remote from an eligible location in the United States. Regular overlap with core US business hours is required. No routine travel is expected.

Work authorization

Applicants must be currently authorized to work in the United States. Trespass Security is not able to provide employment-based immigration sponsorship for this role.

Hiring process

The process has two conversations and no unpaid take-home project.

• An introductory conversation about the role, your experience, and the way Trespass works.
• A technical and final conversation using past work to discuss testing choices, evidence, reporting, and customer communication.

Employment is contingent on completion of a job-related background check conducted in accordance with applicable law. Applicants who need a reasonable accommodation for the application or interview process may email [e-mail] .

Trespass Security is an equal opportunity employer.

Trespass Security provides equal employment opportunities without regard to race, color, religion, sex, pregnancy, sexual orientation, gender identity, national origin, age, disability, genetic information, veteran status, or any other status protected by applicable law.