Lead Security Engineer - AppSec / CloudSec & PenTest / SecOps

## Lead Security Engineer – AppSec / CloudSec & PenTest / SecOpsApply: Hybrid: Boston, MA: Full time: Posted Today: JR-1092**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 FocusThis 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 SummaryAs 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 & RoadmapDefine 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 DefenseDirect 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 LeadershipSet 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 & MentorshipMentor 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.QualificationsMinimum 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 CompetenciesCross-Discipline Credibility: Deep hands-on seniority in application security, cloud architecture defense, penetration testing, or security operations, with the breadth to speak authoritatively across the entire function.Cloud, DevOps & Tooling Stack: Deep practical knowledge spanning public cloud topologies (AWS/Azure/GCP), containerization/orchestration, CI/CD pipelines (GitLab CI), manual penetration testing, and forensic analysis tools.AI Security & Cryptography: Expert-level understanding of the OWASP Top 10 for LLMs, applied cryptography, and federated authentication architectures.Regulatory Compliance: Practical experience aligning security controls with PCI-DSS v4.0, SOC 1, SOC 2, and DORA standards.Leadership Track Record: Proven background mentoring engineers, shaping technical roadmaps, and influencing hiring and resourcing decisions.Preferred CertificationsCloud & Architecture: AWS Certified Security – Specialty, CKS (Certified Kubernetes Security Specialist), or CISSP.Offensive & Red Team: OSCP, OSCE, or SANS GXPN.Incident Response & Defense: GCIH or GCFA.Modern AI Security: OffSec OSAI (Offensive Security AI Red Teamer).Soft Skills & Core MindsetDual Builder/Breaker Mindset: Transitions seamlessly between establishing defensive architecture standards and directing offensive assurance operations.Executive Influence: Leads with influence, skillfully prioritizing competing business priorities and presenting high-impact risks to executive leadership.Crisis Management & Mentorship: Displays calm, analytical decision-making under intense pressure, leveraging crisis scenarios to coach and guide engineers.Commercial Drive: Balances technical risk reduction with enterprise enablement, positioning security as a revenue driver and business differentiator. **What We Offer:*** Competitive compensation* Employee Stock Purchase Plan (ESPP)* Competitive time off* Work with brilliant people globally Learn more about their journeys by checking out #InsideFlywire on social media* Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates* Be a meaningful part in our success - every FlyMate makes an impact* Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers, OneFlywire Career Mobility) **Submit today and get started!** We are excited to get to know you! Throughout our process you can expect to meet with different FlyMates including the Hiring Manager, Peers on the team, the VP of the department, and a skills assessment. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for any questions. Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race, color, religion, sex, pregnancy, gender identity, national origin, age, ancestry, physical or mental disability, sexual orientation, genetic disposition or carrier status, veteran status, or any other category protected under applicable national, federal, state or local law. The base salary for this position is:$0-$0 Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training. #J-18808-Ljbffr