Flywire

Security Engineer II - Offensive Track

Flywire$99K — $120K *
Information Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in Computer Science, Cybersecurity, Software Engineering, or similar field.
  • 1 to 3 years of hands-on experience in penetration testing or a related role.
  • Experience with manual web application testing and vulnerability research.
  • Familiarity with SIEM tools, EDR, and network packet analysis.
  • Basic understanding of AI security and compliance frameworks.

Responsibilities

  • Support penetration testing engagements under senior guidance to gain practical experience.
  • Assist with manual security reviews such as code audits and API testing.
  • Contribute to adversarial testing of AI features, identifying specific weaknesses.
  • Help design and tune SIEM detection rules and alert workflows.
  • Act as a first-line responder during security incidents, documenting findings.
  • Collaborate with team members to communicate testing results and incident metrics.
  • Actively seek mentorship to enhance skills in offensive tooling and incident response.

Benefits

  • Flexible work environment with hybrid options.
  • Opportunities for mentorship from experienced security engineers.
  • Access to ongoing professional development and training.
  • Exposure to a high-paced fintech environment with real impact.
  • Work on innovative projects involving AI security and penetration testing.
Full Job Description
Job Description

Role Focus

At this level, your focus sits within Offensive Penetration Testing and Security Operations, supporting the wider Active Operational Defender track under the guidance of senior engineers. You will assist with manual testing engagements, help tune SIEM detection rules, and support the team during live security incidents, building the operational depth needed to work independently over time.

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.

Key Responsibilities & Tasks (by Priority)
  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, leveraging senior guidance and established detection frameworks.
    • Support SecOps in reviewing detection coverage against current threats using 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
    • Participate in security operations and engineering planning to build a practical understanding of detection and response capabilities.
    • Communicate testing findings and incident metrics clearly to immediate team members and stakeholders.
    • Actively seek mentorship from senior and lead security engineers across offensive tooling, detection engineering, and incident response practices.


Qualifications

Minimum Requirements (Education & Experience)
  • Education: Bachelor's degree in Computer Science, Cybersecurity, Software Engineering, a related technical discipline, or equivalent practical experience.
  • Core Experience: 1 to 3 years of hands-on experience in penetration testing, security operations, or a closely related technical role.

Technical Skills & Knowledge
  • Foundational Offensive Skills: Hands-on exposure to manual web application testing, CTF-style exploitation, or vulnerability research (via work experience, personal projects, or study).
  • SecOps & Forensics: Working knowledge of SIEM concepts, EDR tooling, or network packet analysis, alongside familiarity with frameworks such as MITRE ATT&CK.
  • Scripting / Automation: Proficiency in reading and writing scripts (e.g., Python) to support security testing and automation workflows.
  • AI Security Awareness: Basic working interest in the OWASP Top 10 for LLMs and understanding of how adversarial AI testing differs from traditional app security.
  • Regulatory Context: General understanding of compliance frameworks such as PCI-DSS, SOC 2, or DORA, with a willingness to expand practical knowledge on the job.

Preferred Certifications (Optional / Strongly Encouraged)
  • Offensive & Red Team: OSCP, OSCE, or SANS GXPN.
  • Incident Response & Defense: GCIH, GCFA, or specialized Blue Team certifications.
  • AI Security: OffSec OSAI (Offensive Security AI Red Teamer).

Soft Skills & Mindset
  • Dual Focus: Combines an attacker's drive to uncover vulnerabilities with a defender's discipline to build actionable SIEM detection rules.
  • Composure Under Pressure: Ability to stay calm and analytical during live security breaches or tight production release windows.
  • High-Impact Communication: Capable of translating technical exploit chains and log anomalies into plain language for executive and non-technical stakeholders.
  • Business-Minded Security: Balances risk mitigation with business goals, helping position security as a driver for enterprise growth.


Additional Information

Submit today and get started!

We are excited to get to know you! Throughout our process you can expect to meet different FlyMates including the Hiring Manager and other Flymates. Your Talent Acquisition Partner will walk you through the steps and be your "go-to" person for questions.

The US base salary range for this full-time position is $99,000 - 120,000 and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training.

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About Flywire

Flywire is a financial technology company that provides payment solutions for businesses and institutions. The company was founded in 2009 and is headquartered in Boston, Massachusetts. Flywire's platform allows businesses to accept payments from customers around the world, with support for over 240 countries and 150 currencies. The company's solutions are used by a variety of industries, including education, healthcare, travel, and technology. Flywire has raised over $300 million in funding and has been recognized as one of the fastest-growing companies in the United States.
Learn more about Flywire
Size
500 employees
Market Cap
$2.4 billion
Industry
Founded
2009

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