Senior AppSec Engineer - AI & Cloud Pentester

JobCubby; Boston, Northern (MA, KY); Hybrid; USD 150,000 - 190,000; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

Flexible time-off policy

Parental leave

RRSP match

Wellness reimbursement

Professional development budget

Job summary

Forward Financing, a fintech company based in Boston, is seeking a Senior Application Security Engineer to find vulnerabilities before attackers do. You will pentest core systems and AI-enhanced components, shaping how we test software that AI helped write.

Role requires 5+ years in security, hands-on pentesting across web apps and AWS, and strong communication of risk. The team values flexibility, remote-first work, and collaboration with a fast-moving AI-driven engineering organization.

Qualifications

• 5+ years in application security, offensive security, or product security.
• Hands-on pentesting and code-review depth across web applications, APIs, and AWS.
• Hacker mentality and curiosity about how systems break.
• Interest in using AI to solve problems in workflows or testing.
• Understanding of AI/LLM attack surface: prompt injection, insecure agent tool use, AI-generated code vulnerabilities.
• Experience with modern programming languages such as Ruby, Python, TypeScript, or Go, and secure SDLC practices.
• Ability to communicate risk and priorities to security and software engineers.
• Typically has a Bachelor's Degree in Computer Science or equivalent.

Responsibilities

• Conduct manual penetration tests and build AI-assisted tooling to extend coverage.
• Define how to pentest AI, test LLM applications, agents, and agent-generated code.
• Triage findings from SAST tools, fix real vulnerabilities, and tune rules to reduce false positives.
• Perform secure code reviews across web apps, APIs, and AWS infrastructure.
• Build tooling and security services within the Forward application stack, including AI tooling.
• Support the test-to-production review process to ensure security reviews before promotion.
• Explain risk to engineers to help prioritize fixes.

Skills

Application security

Penetration testing

Code review

AI/LLM testing

Security tooling

Communication of risk

Programming languages

Education

Bachelor's degree in Computer Science or equivalent

Tools

Ruby

Python

TypeScript

Go

Job description

Forward Financing, a fintech company based in Boston, is seeking a Senior Application Security Engineer to find vulnerabilities before attackers do. You will pentest core systems and AI-enhanced components, shaping how we test software that AI helped write.

Role requires 5+ years in security, hands-on pentesting across web apps and AWS, and strong communication of risk. The team values flexibility, remote-first work, and collaboration with a fast-moving AI-driven engineering organization.