Job at a glance
Company Description 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. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.
What more do we need to truly be unstoppable? Perhaps, that is you!  Who we are:  Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We’ve since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.  Today we support more than 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.
With over 1,400 global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.   Job Description Do you spend your free time figuring out how systems break? Are you driven by the thrill of discovering complex vulnerabilities before malicious actors do? If you’re a natural tinkerer who loves attacking systems to make them unshakeable, this role is built for you.
As a Security Engineer II on our Active Operational Offensive track , you’ll sit at the heart of Flywire’s security defenses under the guidance of senior engineers. You will bridge manual penetration testing with active security operations, building the technical depth needed to lead independent engagements over time. Key Responsibilities & Impact 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. Source Code & Vulnerability Analysis: Review SAST/DAST findings and conduct targeted code audits (Python, Java, Ruby) to eliminate false positives and prioritize high-risk fixes. Purple Team Operations: Partner with the Blue Team during adversary emulation exercises to validate security controls, refine enterprise SIEM detection rules, and optimize real-time alerting.
Red Team Engagements: Participate in goal-oriented adversarial simulations evaluating Flywire’s physical/digital posture and incident response readiness. Bug Bounty Operations: Manage external vulnerability disclosure and bug bounty programs, triaging submissions, validating severity, and coordinating swift engineering fixes. Threat Intelligence (MITRE ATT&CK): Apply emerging threat actor TTPs to continuously align testing methodologies with the MITRE ATT&CK framework.
Collaborative Advisory: Deliver actionable remediation guidance to Engineering, SRE, and IT teams, balancing robust security fixes with business velocity. Qualifications Here’s What We’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 env