Lead Security Engineer – AppSec / CloudSec & PenTest / SecOps at Flywire in Boston, MA

Job 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. We’ve 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 5,100 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. Role Focus This is a blended role spanning both the Defensive Platform Builder (AppSec & CloudSec) and Active Operational Defender (PenTest & SecOps) disciplines. You will set the technical direction across both areas, with the opportunity for the scope to adapt based on organizational priorities. Job Summary As Lead Security Engineer, you will set the technical direction for security engineering across both defensive and offensive disciplines, acting as the senior technical authority for the wider team. You will combine deep hands-on credibility with the ability to prioritize, resource, and represent the security engineering roadmap to Cyber leadership and the broader business, while directly mentoring senior and junior engineers across the function. Key Responsibilities & Tasks (by Priority) Technical Strategy & Roadmap Define and own the technical strategy across secure software design, cloud infrastructure defense, offensive testing, and incident detection, aligning priorities with Cyber leadership's wider goals. Represent the security engineering function in cross-functional and executive forums, translating technical risk into clear business impact for non-technical stakeholders. Secure Engineering & Cloud Defense Direct the integration of automated security controls into engineering pipelines and cloud infrastructure, setting the standard that senior and junior engineers build against. Own escalation and final sign-off on complex cloud architecture, Identity and Access Management (IAM), and Zero Trust design decisions. Offensive Assurance & Incident Leadership Set the standard and cadence for penetration testing, red team simulations, and detection engineering across the enterprise estate. Act as the senior technical escalation point during critical security incidents, directing containment and post-incident review efforts. Team Leadership & Mentorship Mentor senior and junior security engineers across both tracks, shaping career development and technical growth within the team. Partner with Talent Acquisition and Cyber leadership on hiring, structuring the security engineering career ladder, and making key resourcing decisions. Qualifications Minimum Requirements (Education & Experience) Education: Bachelor's degree in Computer Science, Cyber Security, Software Engineering, or a related technical discipline required. Master's degree preferred. Core Experience: 8+ years of progressive security engineering experience, demonstrating deep expertise in either the defensive or offensive discipline alongside strong working fluency across both. Technical Expertise & Core Competencies Cross-Discipline Credibility: Deep hands-on seniority in application security, cloud architecture defense, pene