Offensive Security Engineer II - Penetration Testing

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

Job summary

Flywire is seeking a Security Engineer II (Offensive Operations) to join its security team in the United States. The role blends hands-on penetration testing with active security operations across cloud, web applications, and APIs, driving resilience against modern threats.

You'll lead cloud and app assessments, review code for security flaws, coordinate bug bounty activities, and work with Blue/Red teams to validate defenses.

Qualifications

• Bachelor of Science and at least 2+ years’ experience in IT security and penetration testing.
• Hands-on pen-testing across network, web app, and API environments.
• Proficiency with Kali Linux and penetration tools.
• Coding and automation skills with Python, Java, or Ruby.
• Familiar with AWS Cloud infrastructure, CI/CD, and IaC.
• Strong knowledge of OWASP methodologies and threat vectors.
• Excellent written and verbal communication for technical reports.

Responsibilities

• Execute manual internal and external penetration testing across AWS/multicloud environments to identify vulnerabilities, misconfigurations, and privilege escalation paths.
• Perform deep-dive testing on web applications and REST/GraphQL APIs, targeting complex business logic flaws, auth bypasses, and OWASP Top 10 risks.
• Review SAST/DAST findings and conduct targeted code audits to eliminate false positives and prioritize high-risk fixes.
• Partner with the Blue Team during adversary emulation exercises to validate security controls and optimize real-time alerting.
• Participate in goal-oriented Red Team engagements evaluating Flywire’s posture and incident response readiness.
• Manage external vulnerability disclosure and bug bounty programs, triaging submissions and coordinating fixes.
• Apply MITRE ATT&CK framework to testing methodologies and threat intelligence.
• Deliver actionable remediation guidance to Engineering, SRE, and IT teams.

Skills

PenTesting

Bug bounty

Code & Automation

AWS Cloud

SAST/DAST

Python

Java

Ruby

Threat modeling

Technical reporting

Education

Bachelor of Science in IT Security

Tools

Kali Linux

Penetration testing tools

Bug bounty platforms

Job description

Flywire is seeking a Security Engineer II (Offensive Operations) to join its security team in the United States. The role blends hands-on penetration testing with active security operations across cloud, web applications, and APIs, driving resilience against modern threats.

You'll lead cloud and app assessments, review code for security flaws, coordinate bug bounty activities, and work with Blue/Red teams to validate defenses.