Six Figure Work

Senior Director, Head of Enterprise Architecture

Flywire

Company websiteflywire.com (Flywire, opens in new tab)

Base salary $245K  to $295K

Employer-published annual base salary, USD. Advertised base range in Chicago, IL

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  • LocationChicago, IL
  • WorkplaceHybrid
  • Status at last checkSource accepting applications when checked
  • Last checked (1 h ago) · observed since

About this job

Company Description

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 in higher education. We’ve since 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 4,800 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.

With over 1,200 global FlyMates, representing more than 40 nationalities, and in 12 offices world-wide, we’re looking for FlyMates to join the next stage of our journey as we continue to grow.
 

Job Description

The Opportunity:

Flywire is seeking a Head of Architecture to serve as the strategic technical partner to the Chief Technology Officer and lead the evolution of Flywire’s enterprise architecture. This leader will define the long-term architecture strategy for our global payments platform while ensuring our technology ecosystem scales with Flywire’s continued growth.

This role will be responsible for establishing architecture standards, guiding major platform decisions, and driving evolution and modernization across Flywire’s technology stack. The Head of Architecture will partner closely with engineering leadership, product teams, and infrastructure teams to ensure alignment of direction, goals and roadmaps. 

The ideal candidate is a highly experienced enterprise architect who has built and scaled global platforms in complex distributed environments and thrives operating at the intersection of technology strategy and engineering execution. The head of Architecture is first and foremost passionate about Technology, leads with AI first mindset, detailed oriented and hands on when required. 

Key Responsibilities:
Enterprise Architecture Leadership:

  • Define and maintain the enterprise architecture strategy for Flywire’s global payments platform and software solutions. 
  • Establish architecture standards across application, platform, data, and infrastructure layers.
  • Drive architectural alignment, foster a culture of technical excellence and architectural discipline across engineering teams operating globally.
  • Build and mentor a small team of domain and platform architects.

Technology Governance:

  • Lead initiatives to modernize and rationalize different legacy systems and evolve Flywire’s common platform architecture.
  • Guide the adoption of modern architecture patterns including microservices, cloud-native infrastructure, and distributed systems. 
  • Establish architecture governance frameworks including architecture review boards and design standards.
  • Ensure architectural decisions support long-term scalability, security, and compliance requirements while containing or reducing technical debt.

Strategic Technology Leadership:

  • Serve as a strategic advisor to the CTO on technology investment decisions and platform evolution.
  • Evaluate emerging technologies and guide adoption of innovations that improve engineering velocity and platform capabilities.
  • Lead technical due diligence process during M&A and strategic partnership initiatives.

Cross-Functional Collaboration:

  • Partner closely with engineering, product, infrastructure, and security teams to ensure architectural alignment across initiatives.
  • Work with global engineering teams across multiple regions to drive consistent architecture standards

Qualifications

Here’s What We’re Looking For:

  • 15+ years of experience in software engineering and architecture leadership roles.
  • Proven experience as an Enterprise Architect, Chief Architect, or Distinguished Engineer in large-scale technology environments.
  • Deep expertise designing highly scalable distributed systems and cloud-native architectures.
  • Experience building architecture strategies for global platforms handling high-volume transaction workloads.
  • Strong background in microservices architectures, APIs, and event-driven systems.
  • Experience operating in complex regulated industries such as fintech, payments, or financial services.
  • Demonstrated ability to influence engineering organizations and drive architectural standards across distributed teams.
  • Strong collaboration skills with the ability to partner across engineering, product, and executive leadership.
  • Strong communication skills with the ability to represent and advocate Technology matters across the company and including C suite. 
  • Experience leading architecture initiatives within global engineering organizations.
  • Open to Chicago, IL or Austin, TX

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 $245,000-$295,000 plus bonus, 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

Source: Flywire on SmartRecruiters · View original posting (opens in new tab)

Pay in context

This role's base floor ($245,000) is above 98% of the 285 Software Engineering roles in Illinois listed on this site. Their median floor is $143,700; the middle half runs from $120,000 to $168,750.

Only jobs on this site count, and each one publishes a base salary of $100,000 or more, so this compares six-figure jobs with each other, not with the whole market. Computed Nov 8, 2026.

This range next to 4 other live Flywire roles with the nearest advertised base floor
Chart as a table
This range next to 4 other live Flywire roles with the nearest advertised base floor
RolePublished base
Senior Director, Head of Enterprise Architecture (this listing)$245K - $295K
VP, Product Payments Experience & Customer Loyalty$250K - $300K
Senior Director, Enterprise AI & Architecture$200K - $250K
Senior Director, Pricing and Commercial$198K - $225K
Manager, Talent Acquisition, AMER$117K - $146K

Same $100K to $400K scale as every card. All Flywire roles · How to read the bar

Observed changes

  1. First observed on the employer's board
  2. Began meeting the published-salary criteria
Observed since
Employer-stated posting date
2026-07-18
Where this pay comes from

Location as the employer wrote it: Chicago, IL, United States

The US base salary range for this full-time position is $245,000-$295,000 plus bonus, and benefits. Our salary ranges are determined

Method
Employer text, read with fixed rules and re-verified
Checked
Rule set
us-base-v2

The pay passage appears in the employer's own job text. Fixed, deterministic rules located it, and the passage below was checked against the stored copy of the posting.

What we verified

  • The pay figures come from the employer's own listing, quoted exactly above.
  • The pay is an annual base salary in US dollars with a minimum of at least $100,000.
  • The role was publicly listed on the employer's job board when last checked.

We do not verify what the employer will actually offer, whether the employer is still recruiting for the role, or anything beyond what the employer published. Full methodology.

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