Remote Senior Penetration Tester, AI & Cloud Security

Forward Financing; Boston (MA); Hybrid; CAD 143,000 - 183,000; Full time

Benefits offered by this job

Medical

Dental

Vision

Flexible time-off policy

Paid parental leave

RRSP match

Wellness reimbursement

Volunteering days

Annual development budget

Charitable donation match

Job summary

Forward Financing seeks a Senior Penetration Tester to uncover vulnerabilities before attackers do. You will pentest core systems and AI components, define AI security testing approaches, and develop AI-assisted tooling to expand coverage.

You will triage SAST findings, perform code reviews, and explain risk to engineers to prioritize fixes. Remote-first, flexible work options, and competitive compensation are offered.

Qualifications

• 5+ years in application security, offensive security, or product security.
• Hands-on pentesting and code-review depth across web apps, APIs, and cloud infrastructure (AWS).
• A hacker mentality with curiosity about how systems break and persistence after scanners.
• Interest in using AI to solve problems in workflows or systems you test.
• Understanding AI/LLM attack surfaces: prompt injection and insecure agent tools.

Responsibilities

• Conduct manual penetration tests against our systems and build AI-assisted tooling.
• Define how we pentest AI and create tools for testing LLM apps, agents, and generated code.
• Triage findings from SAST tools, fix real vulnerabilities, tune false positives.
• Perform secure code reviews across web apps, APIs, and AWS infrastructure.
• Build tooling and security services within the Forward stack, including AI-assisted tooling.
• Support the test-to-production review process so AI-built work is security-reviewed.
• Explain risk to engineers in actionable terms to guide fixes.

Skills

Application security

Penetration testing

Code review

AI/LLM security

Programming: Ruby

Programming: Python

Programming: TypeScript

Programming: Go

Risk communication

Education

Bachelor27s degree in Computer Science or equivalent

Tools

AWS

SAST tools

Job description

Forward Financing seeks a Senior Penetration Tester to uncover vulnerabilities before attackers do. You will pentest core systems and AI components, define AI security testing approaches, and develop AI-assisted tooling to expand coverage.

You will triage SAST findings, perform code reviews, and explain risk to engineers to prioritize fixes. Remote-first, flexible work options, and competitive compensation are offered.