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Lead Security Engineer – AppSec CloudSec & PenTest SecOps

Flywire


Job Location:

Boston, MA - USA

Monthly Salary: Not provided by the employer
Posted: 9 September 2026 (8 hours ago)
Application Deadline: 7 December 2026
Vacancies: 1 Vacancy

Department:

Security

Job Summary

Role Focus

This is a blended role spanning both the Defensive Platform Builder (AppSec & CloudSec) and Active Operational Defender (PenTest & SecOps) disciplines. You will set the technical direction across both areas with the opportunity for the scope to adapt based on organizational priorities.

Job Summary

As Lead Security Engineer you will set the technical direction for security engineering across both defensive and offensive disciplines acting as the senior technical authority for the wider team. You will combine deep hands-on credibility with the ability to prioritize resource and represent the security engineering roadmap to Cyber leadership and the broader business while directly mentoring senior and junior engineers across the function.

Key Responsibilities & Tasks (by Priority)

  1. Technical Strategy & Roadmap

    • Define and own the technical strategy across secure software design cloud infrastructure defense offensive testing and incident detection aligning priorities with Cyber leaderships wider goals.

    • Represent the security engineering function in cross-functional and executive forums translating technical risk into clear business impact for non-technical stakeholders.

  2. Secure Engineering & Cloud Defense

    • Direct the integration of automated security controls into engineering pipelines and cloud infrastructure setting the standard that senior and junior engineers build against.

    • Own escalation and final sign-off on complex cloud architecture Identity and Access Management (IAM) and Zero Trust design decisions.

  3. Offensive Assurance & Incident Leadership

    • Set the standard and cadence for penetration testing red team simulations and detection engineering across the enterprise estate.

    • Act as the senior technical escalation point during critical security incidents directing containment and post-incident review efforts.

  4. Team Leadership & Mentorship

    • Mentor senior and junior security engineers across both tracks shaping career development and technical growth within the team.

    • Partner with Talent Acquisition and Cyber leadership on hiring structuring the security engineering career ladder and making key resourcing decisions.


Qualifications :

Minimum Requirements (Education & Experience)

  • Education: Bachelors degree in Computer Science Cyber Security Software Engineering or a related technical discipline required. Masters degree preferred.

  • Core Experience: 8 years of progressive security engineering experience demonstrating deep expertise in either the defensive or offensive discipline alongside strong working fluency across both.

Technical Expertise & Core Competencies

  • Cross-Discipline Credibility: Deep hands-on seniority in application security cloud architecture defense penetration testing or security operations with the breadth to speak authoritatively across the entire function.

  • Cloud DevOps & Tooling Stack: Deep practical knowledge spanning public cloud topologies (AWS/Azure/GCP) containerization/orchestration CI/CD pipelines (GitLab CI) manual penetration testing and forensic analysis tools.

  • AI Security & Cryptography: Expert-level understanding of the OWASP Top 10 for LLMs applied cryptography and federated authentication architectures.

  • Regulatory Compliance: Practical experience aligning security controls with PCI-DSS v4.0 SOC 1 SOC 2 and DORA standards.

  • Leadership Track Record: Proven background mentoring engineers shaping technical roadmaps and influencing hiring and resourcing decisions.

Preferred Certifications 

  • Cloud & Architecture: AWS Certified Security Specialty CKS (Certified Kubernetes Security Specialist) or CISSP.

  • Offensive & Red Team: OSCP OSCE or SANS GXPN.

  • Incident Response & Defense: GCIH or GCFA.

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

Soft Skills & Core Mindset

  • Dual Builder/Breaker Mindset: Transitions seamlessly between establishing defensive architecture standards and directing offensive assurance operations.

  • Executive Influence: Leads with influence skillfully prioritizing competing business priorities and presenting high-impact risks to executive leadership.

  • Crisis Management & Mentorship: Displays calm analytical decision-making under intense pressure leveraging crisis scenarios to coach and guide engineers.

  • Commercial Drive: Balances technical risk reduction with enterprise enablement positioning security as a revenue driver and business differentiator.


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.

Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race color religion sex pregnancy gender identity national origin age ancestry physical or mental disability sexual orientation genetic disposition or carrier status veteran status or any other category protected under applicable national federal state or local law.

The US base salary range for this full-time position is $150000 - 180000 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. 

#LI-Hybrid


Remote Work :

No


Employment Type :

Full-time


About Company

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Flywire is a global payments enablement and software company, delivering high-stakes, high-value payments across the global education, healthcare, travel and B2B industries. Today, we’ve digitized payments for more than 4,000+ global clients in more than 140 currencies across 240 cou ... View more

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