Penetration Testing Engineer: AI & Cloud Security

Leadout Capital; California; On-site; USD 110,000 - 160,000; Full time

Job summary

Leadout Capital is seeking a Penetration Testing Engineer to execute deep, hands-on security assessments across web applications, APIs, cloud and AI-enabled systems, and production-like environments. You will bring a hacker mindset to exploit paths beyond checklists, collaborating with engineering, AppSec, and Detection teams.

The role emphasizes scoping, risk assessment, remediation guidance, and clear reporting, with opportunities to work on Kubernetes, Docker deployments, and modern identity

Qualifications

• 2–4 years of hands-on experience in penetration testing, offensive security, or application security testing.
• Experience performing engagements in production or production-like environments using manual techniques and automation/AI tools.
• Understanding of vulnerabilities, attack chains, and cloud/security risks related to AI/LLM-based systems.
• Ability to clearly articulate exploitation mechanics, impact and practical remediation steps to engineers and security teams.

Responsibilities

• Execute penetration tests across web applications, APIs, cloud/hybrid infrastructure (Kubernetes, Docker), identity and trust boundaries, and AI/ML-enabled systems.
• Perform manual exploitation beyond automated tooling, including business logic abuse and privilege escalation.
• Support engagements through scoping, execution, risk assessment, and remediation guidance.
• Produce technically detailed reports covering exploitation paths, missing controls, and mitigation recommendations, collaborating with engineering, AppSec, and Detection & Response teams.

Skills

Penetration testing

Offensive security

Cloud security fundamentals

Identity & access control

Tools

Kubernetes

Docker

AI/ML security tools

Job description

Leadout Capital is seeking a Penetration Testing Engineer to execute deep, hands-on security assessments across web applications, APIs, cloud and AI-enabled systems, and production-like environments. You will bring a hacker mindset to exploit paths beyond checklists, collaborating with engineering, AppSec, and Detection teams.

The role emphasizes scoping, risk assessment, remediation guidance, and clear reporting, with opportunities to work on Kubernetes, Docker deployments, and modern identity