# Security Engineer II (Offensive Operations) at FlyWire

- Company: FlyWire
- What the company does: Are you ready to trade your job for a journey? Become a FlyMate! Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. Backed by Techstars.
- Company website: https://flywirecameras.com
- Type: Startups (AI role)
- Level: Mid level
- Location: Boston, MA
- Work setup: On-site
- Pay: $99K to $120K base salary per year (USD)
- Posted: 2026-09-11
- Apply by: 2026-10-26
- Apply: https://jobs.smartrecruiters.com/Flywire1/744000149049489
- Page: https://www.1752.vc/careers/jobs/flywire-security-engineer-ii-offensive-operations/

## About the role

Cloud Infrastructure PenTesting: Execute manual internal and external penetration testing across AWS/multicloud environments to identify vulnerabilities, misconfigurations, and privilege escalation paths. Web Application & API Assessment: Perform deep-dive testing on web applications and REST/GraphQL APIs, targeting complex business logic flaws, auth bypasses, and OWASP Top 10 risks.

## What they're looking for

- Education & Experience: Bachelor of Science and at least 2+ years’ experience in IT security and Penetration Testing
- Hands-on PenTesting: Demonstrated track record executing network, web application, and API penetration tests
- Offensive Toolset: Proficiency with Kali Linux, commercial/open-source penetration tools, and active involvement on bug bounty platforms
- Code & Automation: Experience with SAST/DAST tools, secure code reviews, and scripting knowledge in Python, Java, or Ruby
- Modern Stack Exposure: Understanding of AWS Cloud infrastructure, Agile environments, CI/CD pipelines, and Infrastructure as Code (IaC)
- Security Frameworks: Strong knowledge of OWASP methodologies, threat vectors (malware, intrusion, DoS), and platform security strategies

Tags: Security