Senior Penetration Tester: AI & Cloud Security (Remote)

Forward Financing LLC; Oregon; Hybrid; USD 143,000 - 183,000; Full time

Benefits offered by this job

Remote-first culture

Job summary

Forward Financing LLC is seeking a Senior Penetration Tester to identify vulnerabilities in our software, AI systems, and AWS infrastructure. You will perform manual pentests, review code, and help shape AI testing strategies while communicating risk to engineers.

We value a hacker mindset, strong security testing skills, and experience with Ruby, Python, TypeScript, or Go. The role offers remote-first work with flexible options and competitive compensation.

Qualifications

• 5+ years in application security, offensive security, or product security.
• Hands-on pentesting and code-review depth across web apps, APIs, and AWS.
• A hacker mentality with curiosity about how systems break.
• Interest in using AI to solve problems in workflows or testing.
• Understanding of AI/LLM attack surfaces: prompt injection, insecure agent use, AI-generated code vulnerabilities.
• Experience with Ruby, Python, TypeScript, or Go and secure SDLC practices.

Responsibilities

• Conduct manual penetration tests against systems and build AI-assisted tooling.
• Define how to pentest AI and test AI-built software.
• Triage findings from SAST tools and fix real vulnerabilities.
• Perform secure code reviews of web apps, APIs, and AWS infra.
• Build security services within the Forward application stack and AI tooling.
• Explain risk to engineers to help them prioritize fixes.

Skills

Application security

Offensive security

AI/LLM security

Ruby

Python

TypeScript

AWS

Education

Bachelor's Degree in Computer Science or equivalent

Tools

AWS

Job description

Forward Financing LLC is seeking a Senior Penetration Tester to identify vulnerabilities in our software, AI systems, and AWS infrastructure. You will perform manual pentests, review code, and help shape AI testing strategies while communicating risk to engineers.

We value a hacker mindset, strong security testing skills, and experience with Ruby, Python, TypeScript, or Go. The role offers remote-first work with flexible options and competitive compensation.