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Flywire is seeking a Lead Security Engineer to set technical direction for security engineering across defensive (AppSec, CloudSec) and offensive (PenTest, SecOps) disciplines. You will act as the senior technical authority for the security engineering team, combining deep hands-on expertise with strategic leadership and mentorship.
Key Responsibilities:
Technical Strategy & Roadmap: Define and own technical strategy across secure software design, cloud infrastructure defence, offensive testing, and incident detection. Represent the security engineering function in cross-functional and executive forums, translating technical risk into business impact for non-technical stakeholders.
Secure Engineering & Cloud Defence: Direct integration of automated security controls into engineering pipelines and cloud infrastructure. Own escalation and final sign-off on complex cloud architecture, Identity and Access Management, and Zero Trust design decisions.
Offensive Assurance & Incident Leadership: Set standards and cadence for penetration testing, red team simulations, and detection engineering. Act as senior technical escalation during critical security incidents, directing containment and post-incident review.
Team Leadership & Mentorship: Mentor senior and junior security engineers across both tracks, shaping career development and technical growth. Partner with Talent Acquisition and Cyber leadership on hiring, career ladder structuring, and resourcing decisions.
Flywire is a global payments enablement and software company supporting 5,300+ clients across education, healthcare, travel, and B2B industries, with 1,400+ employees across 15 offices worldwide.
Requirements:
- Bachelor's degree in Computer Science, Cyber Security, Software Engineering, or related technical discipline (Master's preferred)
- 8+ years of progressive engineering experience with demonstrated depth in either defensive or offensive security discipline and strong working fluency across both
- Hands-on seniority in application security, cloud architecture defence, penetration testing, or security operations
- Deep practical knowledge of public cloud topologies, containerization and orchestration, GitLab CI pipelines, and manual testing/forensic tooling
- Expert-level understanding of OWASP Top 10 for LLMs, applied cryptography, and federated authentication architectures
- Practical experience aligning controls to PCI-DSS (v4.0), SOC 1, SOC 2, and DORA
- Prior experience mentoring engineers, shaping technical roadmaps, or influencing hiring/resourcing decisions
Highly Preferred Certifications:
- AWS Certified Security - Specialty, CKS, or CISSP
- OSCP, OSCE, or SANS GXPN
- GCIH or GCFA
- OffSec OSAI (Offensive Security AI Red Teamer)
Key Skills:
- Moves credibly between builder and breaker mindsets
- Leads with influence; able to prioritize competing security priorities and represent them to executives
- Brings calm, analytically clear decision-making under pressure
- Balances technical risk reduction with business enablement
