Security Engineer II (Defensive Operations)

Flywire • Boston, MA

4d

About The Position

Flywire is seeking a Security Engineer II to join its global Security Engineering team. The role spans secure software design, cloud-native infrastructure defense, offensive penetration testing, and real-time incident detection. It combines an attacker’s mindset with engineering empathy and an automation-first approach in a high-velocity fintech environment. The engineer will partner with software engineering, SRE, and DevOps teams to integrate security controls into public cloud infrastructure and GitLab CI/CD pipelines, while contributing to threat detection, red teaming, and incident containment.

The position includes building automated security controls and internal tools; establishing secure cloud and container architecture; designing AI-supported security reviews and safeguards for generative AI features; conducting penetration tests and code audits; responding to incidents and improving SIEM detections; and collaborating with engineering teams from the start of development while mentoring junior engineers.

Requirements

• Bachelor’s degree in Computer Science, Cyber Security, Software Engineering, or a related technical discipline, or equivalent experience.
• At least 3 years of progressive engineering experience spanning application security, cloud architecture defense, and active security operations such as incident response or penetration testing.
• Demonstrated ability to independently perform manual penetration testing, web application exploitation, and incident containment without relying solely on commercial automated scanners.
• Practical knowledge of AWS or public cloud topologies, Docker, Kubernetes, network security, and building or maintaining GitLab CI pipelines.
• Foundational proficiency with modern web development frameworks and programming languages, including Python, Ruby on Rails, Java, or Node.js.
• Understanding of the OWASP Top 10 for LLMs, applied cryptography, cloud network isolation, and federated authentication architectures including OAuth2, SAML, OIDC, and Zero Trust IAM.
• Working proficiency with EDR platforms, SIEM systems, network packet analysis (PCAP), MITRE ATT&CK, and forensic collection tools.
• Practical experience aligning software and infrastructure controls with PCI-DSS v4.0, SOC 1, SOC 2, or DORA.

Nice To Haves

• OSCP, OSCE, or SANS GXPN certification.
• AWS Certified Security - Specialty, CKS, or CISSP certification.
• GCIH, GCFA, or specialized Blue Team certification.
• OffSec OSAI certification.

Responsibilities

• Design and drive integration of automated security requirements and validation tools into engineering pipelines.
• Build internal tooling, wrappers, and automated controls that support development velocity.
• Partner with SRE and DevOps teams on secure cloud architecture, Terraform infrastructure-as-code security scans, and Zero Trust boundaries in containerized environments.
• Design and deploy automated security review workflows using LLM APIs, and establish safeguards for generative AI features.
• Conduct manual source-code audits, API exploitation, cloud penetration testing, exploit research, and red-team activities.
• Lead technical containment, forensic collection, and threat eradication during active security incidents.
• Design and deploy high-fidelity SIEM detection rules and automated alert workflows.
• Participate in software development and infrastructure sprint planning to integrate security from inception.
• Provide actionable code modifications and mentor junior engineers.

Benefits

• Competitive compensation.
• Employee Stock Purchase Plan (ESPP).
• Competitive time off.
• Wellbeing programs, including mental health, wellness, and yoga, Pilates, and HIIT classes.
• Talent and development programs, including Managers Taking Flight and OneFlywire Career Mobility.
• Opportunity to work with colleagues globally and contribute meaningfully to company success.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level