Senior Pen Test: AI Security & Automation (Remote)

Forward Financing LLC; Boston (MA); Hybrid; CAD 205,000 - 259,000; Full time

Benefits offered by this job

Remote-first culture

Flexible work locations

Professional development budget

Wellness reimbursement

Job summary

Forward Financing LLC is seeking a Senior Penetration Tester to find vulnerabilities in software, including AI systems, before attackers do. You will pentest core systems and AI-driven components and shape how we test AI-built software.

You will build AI-assisted tooling, review secure code across web apps, APIs, and AWS, and clearly explain risk to engineers to drive fixes. This remote-first role offers collaboration across teams and strong growth opportunities.

Qualifications

• 5+ years in application security or product security.
• Hands-on pentesting and code-review depth across web apps, APIs, and AWS.
• Curious and persistent mindset with a hacker mentality.
• Interest in using AI to solve problems and test AI-built software.
• Understanding AI/LLM attack surface and related vulnerabilities.

Responsibilities

• Conduct manual penetration tests against systems and AI components.
• Build AI-assisted tooling to extend testing coverage.
• Define how to pentest AI and test agent-generated code.
• Triage findings from SAST tools and fix true vulnerabilities.
• Perform secure code reviews across web apps, APIs, and AWS.
• Explain risk to engineers to help prioritize fixes.

Skills

Application security

Penetration testing

Code review

AWS

AI/LLM testing

Education

Bachelor's Degree in Computer Science

Tools

Ruby

Python

TypeScript

Go

Job description

Forward Financing LLC is seeking a Senior Penetration Tester to find vulnerabilities in software, including AI systems, before attackers do. You will pentest core systems and AI-driven components and shape how we test AI-built software.

You will build AI-assisted tooling, review secure code across web apps, APIs, and AWS, and clearly explain risk to engineers to drive fixes. This remote-first role offers collaboration across teams and strong growth opportunities.