Offensive Security Engineer: Pen-Testing & Red Team Ops

Flywire; Boston (MA); On-site; USD 90,000 - 120,000; Full time

Job summary

Flywire is seeking a Security Engineer II to join our Active Operational Offensive track in Boston. You will bridge manual penetration testing with active security operations, driving hands-on assessments across cloud, web, and API surfaces.

You will partner with engineering and IT teams to prioritize fixes, improve detections, and lead engagements that validate security controls in real-time.

Qualifications

• Bachelor’s degree in IT security or related field; 2+ years in IT security/pen testing.
• Experience conducting network, web, and API penetration tests.
• Familiarity with security frameworks and vulnerability remediation.

Responsibilities

• Perform manual internal and external penetration testing across AWS/multicloud environments to identify vulnerabilities.
• Test web applications and REST/GraphQL APIs for complex logic flaws and auth bypasses.
• Review SAST/DAST findings and conduct targeted code audits in Python, Java, or Ruby.
• Collaborate with the Blue Team to refine SIEM detection rules and threat intel usage.
• Support Red Team engagements and bug bounty triage and coordination.
• Apply MITRE ATT&CK to testing methodologies and improve coverage.
• Provide remediation guidance to Engineering, SRE, and IT teams.

Skills

Penetration testing

Blue team collaboration

Threat intelligence

Python/Java/Ruby

OWASP

AWS

SAST/DAST

Kali Linux

Bug bounty

Adversary emulation

Education

Bachelor’s degree in IT security

Tools

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Job description

Flywire is seeking a Security Engineer II to join our Active Operational Offensive track in Boston. You will bridge manual penetration testing with active security operations, driving hands-on assessments across cloud, web, and API surfaces.

You will partner with engineering and IT teams to prioritize fixes, improve detections, and lead engagements that validate security controls in real-time.