Penetration Testing Engineer, MTS

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

Penetration Testing Engineer, MTS

The Experience

We are looking for a Penetration Testing Engineer to execute deep, hands-on penetration tests across our applications, platforms, cloud infrastructure, and AI-powered systems. You’ll bring a hacker mindset to real exploitation and attack chaining rather than checklist-driven testing, working under the guidance of senior team members on complex engagements.
You’ll partner with engineering and AppSec teams to turn findings into concrete remediation, while building your skills across cloud, identity, and AI/ML attack surfaces.

What You’ll Actually Be Doing

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

You're Our Person If...

• You have 2-4 years of hands-on experience in penetration testing, offensive security, or application security testing.
• You have experience performing penetration testing engagements in production or production-like environments, using manual techniques and automation/AI tools.
• You understand application security vulnerabilities and attack chains, identity and access control failures, cloud security fundamentals, and security risks specific to AI and LLM-based systems.
• You can clearly articulate exploitation mechanics, impact, and practical remediation steps to engineers and security teams.

Even Better If...

• You have experience with custom scripts, payloads, or proof-of-concept development.
• You've participated in Bug Bounty programs.
• You're familiar with cloud architectures and identity-centric security models.
• You have experience using AI/LLMs for offensive security work or vulnerability discovery.