Security Engineer II (Offensive)

Are you ready to trade your job for a journey? Become a FlyMate!

Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.

What more do we need to truly be unstoppable? Perhaps, that is you!

Who we are:

Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments. We’ve scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.

Today we support more than 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,400+ global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.

Job Summary:

As a Security Engineer II on the Active Operational Defender track you will build hands on experience across penetration testing, threat detection and incident response, working under the direction of senior and lead engineers. You will support live operational work within a high velocity fintech environment, developing the manual testing and detection engineering skills needed to take on more independent responsibility over time.

Responsibilities and Tasks:

1. Offensive Penetration Testing & Red Teaming

• Support penetration testing engagements across financial platforms and product architectures under senior guidance, building practical exploit research experience.

• Assist with manual security reviews including source code audits, API testing and cloud configuration checks, working towards independent delivery of smaller engagements.

• Contribute to adversarial testing of AI features where in scope, learning to identify prompt injection and related LLM specific weaknesses.

2. Threat Detection Engineering & SIEM

• Help design and tune detection rules and alert workflows within the enterprise SIEM, working from senior engineers' guidance and established detection frameworks.

• Support SecOps in reviewing detection coverage against current threats, referencing frameworks such as MITRE ATT&CK.

3. Incident Response & Forensics

• Act as a first line responder during active security incidents, carrying out evidence collection and initial triage under senior direction.

• Support post incident analysis by pulling together logs, timelines and technical findings for senior review.

4. Cross Functional Collaboration & Development

• Take part in security operations and engineering planning to build a practical understanding of detection and response capability.

• Communicate findings from testing and incidents clearly to immediate team members and stakeholders.

• Actively seek mentorship from senior and lead security engineers on offensive tooling, detection engineering and incident response practice.

• Education: Bachelor's degree in Computer Science, Cyber Security, Software Engineering or a related technical discipline, or equivalent practical experience.

• Core Experience: indicative range [1 to 3 years] of hands on experience in penetration testing, security operations or a closely related technical role.

• Foundational Offensive Skills: exposure to manual web application testing, CTF style exploitation or vulnerability research, gained through work experience, personal projects or study.

• SecOps & Forensics Familiarity: basic working knowledge of SIEM concepts, EDR tooling or network packet analysis, and an interest in frameworks such as MITRE ATT&CK.

• Technical Language Foundation: comfort reading and, ideally, writing scripts in a language such as Python to support testing and automation.

• AI Security Awareness: a working interest in the OWASP Top 10 for LLMs and how adversarial testing of AI features differs from traditional application testing.

• Regulatory Awareness: a general understanding of standards such as PCI-DSS, SOC 2 or DORA, with willingness to build practical depth on the job.

  Highly Preferred Certifications

• Hands-On Offensive & Red Team: OSCP, OSCE or SANS GXPN (GIAC Exploit Researcher and Advanced Penetration Tester).

• Incident Response & Defence: GCIH (GIAC Certified Incident Handler), GCFA (GIAC Certified Forensic Analyst) or a specialised Blue Team certification.

  Skills and Abilities

• Combines an aggressive, attacker's mindset used to find vulnerabilities with the analytical discipline required to write clear, actionable detection rules.

• Stays calm and analytically clear under intense pressure during active, live breach events or business critical system failures.

• Communicates exploit chains and log anomalies clearly, turning technical detail into a plain, high impact risk profile for non-technical leadership.

• Resilience and analytical clarity in high-pressure scenarios, supporting transparent communication and contributing to risk-based decisions during active security incidents or compressed financial product launch windows.

• Balances technical risk reduction with business enablement, supporting security infrastructure that serves as a competitive advantage and helps unblock global revenue and enterprise-client acquisition.

• Modern AI Security: OffSec OSAI (Offensive Security AI Red Teamer).

What We Offer:

• Competitive compensation
• Employee Stock Purchase Plan (ESPP)
• Competitive time off, including Digital Disconnect and FlyBetter Days to volunteer in a cause you believe in.
• Flying Start - Our immersive Global Induction Program (Meet our Execs & Global Teams)
• Work with brilliant people globally Learn more about their journeys by checking out #InsideFlywire on social media
• Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates
• Be a meaningful part in our success - every FlyMate makes an impact
• Great Talent & Development Programs (Managers Taking Flight - for new or aspiring managers, OneFlywire Career Mobility)

Submit today and get started!

We are excited to get to know you! Throughout our process you can expect to meet with different FlyMates including the Hiring Manager, Peers on the team, the VP of the department, and a skills assessment. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for any questions.