Full-Time

Lead Security Engineer

Application Security / Cloud Security, Penetration Testing / Security Operations

Posted on 9/8/2026

Flywire

Flywire

1,001-5,000 employees

Global payments platform for education, healthcare

Compensation Overview

$150k - $180k/yr

Boston, MA, USA

Hybrid

Hybrid work arrangement in Boston.

Bachelor's, Master's

Category
Cybersecurity (2)
,
Required Skills
Microsoft Azure
Incident Response
Docker
SOC 2
AWS
Cryptography
Penetration Testing
DevOps
Google Cloud Platform

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Requirements
  • A bachelor's degree in Computer Science, Cyber Security, Software Engineering, or a related technical discipline is required.
  • 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 the breadth to speak authoritatively across the entire function.
  • Deep practical knowledge of public cloud topologies including Amazon Web Services, Microsoft Azure, or Google Cloud Platform; containerization and orchestration; continuous integration and continuous delivery pipelines using GitLab CI; manual penetration testing; and forensic analysis tools.
  • Expert-level understanding of the OWASP Top 10 for Large Language Models, applied cryptography, and federated authentication architectures.
  • Practical experience aligning security controls with PCI-DSS v4.0, SOC 1, SOC 2, and DORA standards.
  • A proven background mentoring engineers, shaping technical roadmaps, and influencing hiring and resourcing decisions.
  • Ability to transition between defensive architecture standards and offensive assurance operations.
  • Ability to prioritize competing business priorities and present high-impact risks to executive leadership.
  • Ability to make calm, analytical decisions under intense pressure and coach and guide engineers during crisis scenarios.
  • Ability to balance technical risk reduction with enterprise enablement.
Responsibilities
  • Define and own the technical strategy across secure software design, cloud infrastructure defense, offensive testing, and incident detection, aligning priorities with Cyber leadership's wider goals.
  • Represent the security engineering function in cross-functional and executive forums, translating technical risk into clear business impact for non-technical stakeholders.
  • Direct the integration of automated security controls into engineering pipelines and cloud infrastructure, setting the standard for senior and junior engineers.
  • Own escalation and final sign-off on complex cloud architecture, Identity and Access Management, and Zero Trust design decisions.
  • 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.
  • 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.
  • Set the technical direction for security engineering across defensive and offensive disciplines and represent the security engineering roadmap to Cyber leadership and the broader business.
Desired Qualifications
  • A master's degree.
  • AWS Certified Security – Specialty, Certified Kubernetes Security Specialist, or CISSP.
  • OSCP, OSCE, or SANS GXPN.
  • GCIH or GCFA.
  • OffSec OSAI (Offensive Security AI Red Teamer).

Flywire provides global payments enablement and software for high-value cross-border payments across education, healthcare, travel, and B2B. It combines a payments platform, a global network, and vertical-specific software to manage invoicing, payment, and receivables, integrating with clients' ERP and A/R systems; it supports 140+ currencies across 240+ countries and local currency payments with installment options. It differentiates itself by vertical-focused software and end-to-end receivables workflow embedded in clients' systems rather than a generic processor. Its goal is to simplify and streamline complex, high-value payments for institutions and enterprises worldwide while expanding its geographic and industry reach.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

Boston, Massachusetts

Founded

2011

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Simplify Jobs

Simplify's Take

What believers are saying

  • Q2 2026 revenue rose 27.2% to $167.7 million, with EBITDA up 44.5%.
  • Flywire raised 2026 guidance to 21%-27% FX-neutral growth and roughly 23% EBITDA margin.
  • AI cut payer support tickets 40%, while over 200 new clients signed in Q2.

What critics are saying

  • Flywire still depends heavily on education, while U.S. and U.K. visa cuts hit demand.
  • A 2025 securities class action alleges Flywire overstated growth and hid visa impacts.
  • February 2026 layoffs cut 10% of staff, signaling cost pressure and execution strain.

What makes Flywire unique

  • Flywire owns complex, high-value payments in education, healthcare, travel, and B2B.
  • Its workflow embeds reconciliation into clients’ AR and ERP systems across 240 countries.
  • Sertifi adds hospitality software, widening Flywire beyond pure payments into embedded vertical workflows.

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Benefits

Health Insurance

401(k) Retirement Plan

Wellness Program

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-2%

2 year growth

0%
Yahoo Finance
Aug 13th, 2026
Flywire beats Q2 revenue estimates with $164M, guides Q3 above expectations at $231M

Flywire reported second quarter results that beat analyst expectations on revenue and adjusted EBITDA. The company posted revenue of $163.8 million, up 28.5% year-on-year and 4.5% above estimates. Adjusted EBITDA came in at $24.04 million, beating forecasts by 11.4%. CEO Michael Massaro attributed the performance to broad-based growth across education, travel, and B2B payments. The company's guidance for third quarter revenue of $231 million exceeded analyst estimates of $229.1 million. During the earnings call, analysts probed management on proposed US visa regulations, business mix at $1 billion revenue, cross-sell opportunities, margin dynamics between domestic and cross-border volumes, and AI implementation costs. Flywire said its guidance assumes a prudent 30% visa decline and noted that digital transformation investments are driving productivity gains.

Yahoo Finance
Aug 5th, 2026
Flywire beats Q2 expectations with 28% revenue growth to $164M, raises 2026 outlook

Flywire exceeded second-quarter expectations, with revenue less ancillary services rising 28% year-over-year to $164 million and adjusted EBITDA reaching $24 million. Transaction revenue increased 35% to $135.9 million, supported by 43% growth in transaction payment volume. Travel, hospitality, healthcare, and B2B payment-processing drove growth. The company raised its 2026 outlook to 21%–27% FX-neutral revenue growth and approximately 23% adjusted EBITDA margin at midpoint. Flywire projects more than $50 million in GAAP net income and 70%–75% free-cash-flow conversion. The company remains cautious about international education due to visa and regulatory pressures, but is diversifying geographically and expanding its Student Financial Services platform, hospitality business, and AI-driven automation initiatives.

Yahoo Finance
Aug 3rd, 2026
Flywire expects 22.8% revenue growth ahead of Q2 earnings report

Flywire will report Q2 earnings on Tuesday after market hours. The global payments company beat revenue expectations last quarter with $184 million, up 42.9% year-on-year. Analysts expect Q2 revenue to grow 22.8% year-on-year, down from the 27.7% increase in the same quarter last year. Analysts have largely reconfirmed their estimates over the past 30 days. Flywire has missed Wall Street's revenue estimates multiple times over the last two years. The finance and HR software segment has seen positive investor sentiment, with share prices up 2.7% on average over the last month. Flywire's shares are down 12.7% during the same period. The stock currently trades at $16.01, below the average analyst price target of $19.31.

Yahoo Finance
Jul 5th, 2026
Flywire reports 41% revenue growth as US-Iran ceasefire could boost travel payments

Flywire and Airbnb could benefit from a potential US-Iran ceasefire, which may boost consumer confidence, lower fuel costs, and restore flight routes. Flywire, a global payments enablement company, reported 41% year-over-year revenue growth in Q1 2026. Analysts project earnings growth of approximately 111% in the coming year. The company facilitates cross-border transactions across travel, education, healthcare, and commercial services. Airbnb's revenue rose 18% year-over-year to $2.7 billion. The company estimates the Middle East conflict weighed about 100 basis points on nights and seats. A post-ceasefire scenario could increase stability in the travel industry. Both companies stand to benefit from increased international travel, though the extent of benefits may vary across different global regions.

Yahoo Finance
Jun 23rd, 2026
Flywire chief payments officer sells 54,000 shares worth $827,000

Flywire Corporation's Chief Payments Officer Mohit Kansal sold 54,000 shares for approximately $827,000 in an open-market transaction, according to an SEC Form 4 filing. The shares were sold at a weighted average price of around $15.15, near the 15 June 2026 closing price of $15.31. This represents Kansal's largest single sale on record, constituting 9.8% of his direct ownership. Following the transaction, he retains 504,320 shares, representing 0.41% of outstanding shares, with a value of approximately $7.72 million. Flywire shares had appreciated 43% over the previous year as of the transaction date. The company provides global payment processing platforms for education, healthcare, travel and business-to-business sectors, with a market capitalisation of $1.89 billion.