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.
Open position
Senior Penetration Tester
Own authorized penetration tests from scoping input through careful investigation, clear reporting, customer review, and retesting.
US remoteFull-time W-2End-to-end deliveryOpen until filled
The role
Lead clear, defensible testing engagements.
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.
- Shape an authorized scope
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.
Position details
Employment, location, and authorization.
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.
How to apply
Start with a resume and a brief note.
Email your resume and a brief note describing your relevant penetration-testing and report-writing experience.
Apply for this roleWe use application materials to evaluate your candidacy and may retain them for future roles for up to 12 months. You may opt out or request deletion by following the instructions in our Privacy Policy. Do not send customer data, credentials, exploit code, vulnerability evidence, or other confidential materials.
Hiring process
We focus on how you test, reason, and report.
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 careers@trespasssec.com.
Equal opportunity
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.