Senior Penetration Tester & Technical Lead - Remote

Trespass Security LLC; Northern (KY); Hybrid; USD 140,000 - 190,000; Full time

Job summary

Trespass Security LLC is seeking a senior security testing leader to drive complex web application, API, network, and cloud penetration engagements. You will stay hands-on while supervising others, setting practices, and ensuring findings are accurate, actionable, and defensible.

The role is full-time and fully remote from any eligible US location, requiring overlap with core US business hours and adherence to written authorization and engagement rules.

Qualifications

• Principal or lead-level experience owning penetration tests and reviewing others.
• Deep capability in web application and API testing across network and cloud surfaces.
• Ability to validate complex findings and distinguish impact from speculation.
• Experience in final technical-review decisions and method exceptions.
• Strong customer communication under scope and safety constraints.

Responsibilities

• Lead complex penetration tests within written authorization and ROE.
• Review difficult findings, guide scope and safety decisions.
• Coach practitioners and improve repeatable methods.
• Ensure evidence, planning, and reporting standards are robust.

Skills

Web application testing

API testing

Network security

Cloud security

Technical leadership

Education

Security-related degrees/certifications welcome but not required

Job description

Trespass Security LLC is seeking a senior security testing leader to drive complex web application, API, network, and cloud penetration engagements. You will stay hands-on while supervising others, setting practices, and ensuring findings are accurate, actionable, and defensible.

The role is full-time and fully remote from any eligible US location, requiring overlap with core US business hours and adherence to written authorization and engagement rules.