Security Engineer II: Offensive Operations (Hybrid)

Flywire; Boston (MA); Hybrid; USD 99,000 - 120,000; Full time

Job summary

Flywire is seeking a Security Engineer II (Offensive Operations) to join our active operations team. You will bridge manual penetration testing with real-time security operations across AWS/multicloud environments.

You will analyze code, conduct purple team exercises, and coordinate bug bounty programs while aligning with MITRE ATT&CK and OWASP guidance. Strong scripting and red team mindset required.

Qualifications

• Hands-on PenTesting across networks, web apps, and APIs.
• Experience with AWS and multi-cloud environments.
• Review SAST/DAST findings and perform code reviews.
• Proficient with Python/Java/Ruby scripting.
• Knowledge of OWASP and threat vectors.

Responsibilities

• Execute manual internal and external penetration testing across AWS/multicloud environments.
• Perform deep-dive testing on web apps and APIs for complex logic flaws and auth bypasses.
• Review code scan results and triage vulnerabilities with engineering teams.
• Collaborate with Red/Blue teams to improve detection and response.
• Lead bug bounty triage and disclosure coordination.

Skills

Penetration Testing

Python

Java

Ruby

Scripting

AWS Cloud

OWASP

Threat Modeling

Blue/Red Team

Education

Bachelor of Science

Tools

Kali Linux

Burp Suite

SAST/DAST tools

Job description

Flywire is seeking a Security Engineer II (Offensive Operations) to join our active operations team. You will bridge manual penetration testing with real-time security operations across AWS/multicloud environments.

You will analyze code, conduct purple team exercises, and coordinate bug bounty programs while aligning with MITRE ATT&CK and OWASP guidance. Strong scripting and red team mindset required.