Offensive Security Engineer II – Hybrid PenTest

Flywire; Boston (MA); Hybrid; USD 120,000 - 160,000; Full time

Benefits offered by this job

ESPP

Competitive time off

Wellbeing & mental health programs

Global collaboration

Job summary

Flywire is seeking a Security Engineer II to perform offensive security testing across AWS and multi-cloud environments. You’ll bridge manual penetration testing with active security operations, contributing to red/blue team exercises and improving detection rules.

The role emphasizes practical exploit research, threat-informed testing, and collaboration with engineering, SRE, and IT to balance security with velocity.

Qualifications

• Bachelor of Science and at least 2+ years’ experience in IT security and Penetration Testing.
• Hands-on Pentesting across network, web apps, and APIs.
• Knowledge of AWS Cloud, CI/CD, IaC, and modern security tooling.

Responsibilities

• Execute manual internal/external penetration tests across cloud environments.
• Assess web apps and APIs for complex logic flaws and auth bypasses.
• Review code/security findings and triage fixes with engineering teams.
• Collaborate with Blue Team during adversary emulations and improve SIEM rules.

Skills

Penetration testing

Security strategy

Communication

Education

Bachelor's degree in IT security

Tools

Kali Linux

SAST/DAST tools

Python/Java/Ruby scripting

Job description

Flywire is seeking a Security Engineer II to perform offensive security testing across AWS and multi-cloud environments. You’ll bridge manual penetration testing with active security operations, contributing to red/blue team exercises and improving detection rules.

The role emphasizes practical exploit research, threat-informed testing, and collaboration with engineering, SRE, and IT to balance security with velocity.