Lead Security Engineer – AppSec / CloudSec & PenTest / SecOps

Flywire • Boston, MA

8d • $132,300 - $189,000

About The Position

The Lead Security Engineer sets technical direction for security engineering across defensive and offensive disciplines, including application security, cloud security, penetration testing, and security operations. The role combines hands-on technical expertise with responsibility for prioritizing and resourcing the security engineering roadmap, representing the function to Cyber leadership and the broader business, and mentoring engineers across the team. The scope may adapt to organizational priorities.

The role defines strategy across secure software design, cloud infrastructure defense, offensive testing, and incident detection. It directs the integration of automated security controls into engineering pipelines and cloud infrastructure; provides final technical escalation and sign-off for complex cloud architecture, IAM, and Zero Trust decisions; establishes the cadence and standards for penetration testing, red-team simulations, and detection engineering; and leads technical response and post-incident reviews for critical security incidents.

The Lead Security Engineer also mentors senior and junior engineers, supports hiring and career-ladder development, and makes resourcing decisions with Talent Acquisition and Cyber leadership. The position requires at least eight years of progressive security engineering experience and a bachelor's degree in a related technical discipline. The posted US base salary range is $132,300–$189,000, with individual pay dependent on work location and other job-related factors.

Requirements

• Bachelor's degree in Computer Science, Cyber Security, Software Engineering, or a related technical discipline.
• At least 8 years of progressive security engineering experience, with deep expertise in either defensive or offensive security and strong working fluency across both.
• Deep hands-on seniority in application security, cloud architecture defense, penetration testing, or security operations, with breadth across the wider security engineering function.
• Practical knowledge of public cloud topologies including AWS, Azure, and GCP; containerization and orchestration; CI/CD pipelines including GitLab CI; manual penetration testing; and forensic analysis tools.
• Expert-level understanding of the OWASP Top 10 for LLMs, applied cryptography, and federated authentication architectures.
• Practical experience aligning security controls with PCI-DSS v4.0, SOC 1, SOC 2, and DORA standards.
• Proven experience mentoring engineers, shaping technical roadmaps, and influencing hiring and resourcing decisions.
• Ability to establish defensive architecture standards and direct offensive assurance operations.
• Ability to prioritize competing business needs and present high-impact risks to executive leadership.
• Calm, analytical decision-making under pressure, with the ability to use crisis scenarios to coach and guide engineers.
• Ability to balance technical risk reduction with enterprise enablement and position security as a business differentiator.

Nice To Haves

• Master's degree.
• AWS Certified Security – Specialty, CKS (Certified Kubernetes Security Specialist), or CISSP.
• OSCP, OSCE, or SANS GXPN.
• GCIH or GCFA.
• OffSec OSAI (Offensive Security AI Red Teamer).

Responsibilities

• Define and own technical strategy across secure software design, cloud infrastructure defense, offensive testing, and incident detection, aligning priorities with Cyber leadership's goals.
• Represent security engineering in cross-functional and executive forums, translating technical risk into clear business impact.
• Direct integration of automated security controls into engineering pipelines and cloud infrastructure, setting standards for engineers.
• Own escalation and final sign-off on complex cloud architecture, IAM, and Zero Trust design decisions.
• Set standards 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 reviews.
• Mentor senior and junior security engineers and guide their career development and technical growth.
• Partner with Talent Acquisition and Cyber leadership on hiring, security engineering career-ladder structure, and resourcing decisions.

Benefits

• Competitive compensation.
• Employee Stock Purchase Plan (ESPP).
• Competitive time off.
• Wellbeing programs, including mental health, wellness, and yoga, Pilates, and HIIT classes.
• Talent and development programs, including Managers Taking Flight and OneFlywire Career Mobility.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior