Security Engineer II: Offensive Operations & PenTesting

Flywire; Massachusetts; Hybrid; USD 99,000 - 120,000; Full time

Job summary

Flywire is seeking a Security Engineer II on the Active Operational Offensive track. You will blend manual penetration testing with active security operations, collaborating with the Blue Team and bug bounty programs to strengthen defenses across AWS and multi-cloud environments.

Ideal candidates have 2+ years in IT security, hands-on pen testing, and scripting in Python, Java, or Ruby, with knowledge of MITRE ATT&CK and OWASP methodologies. Hybrid US role with competitive compensation.

Qualifications

• Bachelor of Science in IT security or related field; 2+ years of hands-on IT security/pen testing experience.
• Experience conducting network, web app, and API penetration tests.
• Proficiency with Kali Linux and commercial/open-source pen testing tools.
• Scripting knowledge in Python, Java, or Ruby; familiarity with SAST/DAST.
• Understanding of AWS cloud infrastructure, CI/CD, and IaC.
• Familiarity with OWASP methodologies and threat vectors.

Responsibilities

• Cloud Infrastructure PenTesting across AWS/multicloud environments to identify vulnerabilities.
• Web Application & API testing targeting complex logic flaws and OWASP Top 10 risks.
• Code & vulnerability analysis reviewing SAST/DAST findings and prioritizing fixes.

Skills

PenTesting

Python

Java

Ruby

AWS

CI/CD

IaC

SAST/DAST

Education

Bachelor of Science in IT Security

Tools

Kali Linux

Penetration Tools

Bug Bounty Platforms

Job description

Flywire is seeking a Security Engineer II on the Active Operational Offensive track. You will blend manual penetration testing with active security operations, collaborating with the Blue Team and bug bounty programs to strengthen defenses across AWS and multi-cloud environments.

Ideal candidates have 2+ years in IT security, hands-on pen testing, and scripting in Python, Java, or Ruby, with knowledge of MITRE ATT&CK and OWASP methodologies. Hybrid US role with competitive compensation.