Senior Director, B2B Engineering, Americas Site Lead

Job Description

The Opportunity
Flywire is seeking a Senior Director, B2B Engineering to lead and scale our B2B engineering organization across the Americas, with a strong preference for this leader to be based in Austin, Texas. This is a critical leadership role at the intersection of engineering strategy, payments innovation, AI-first product development, and site leadership.

• Own the technology strategy and execution for Flywire’s B2B business, partnering closely with Product, Commercial, Operations, and Engineering leadership.
• Define and deliver the technology roadmap for Flywire’s B2B business.
• Build and scale a high-performing internal engineering team, reducing dependency on external contractors and strengthening Flywire’s internal IP, technical depth, and operating leverage.
• Serve as the Americas engineering site lead, helping establish Austin as a strategic technology hub and creating the foundation for future engineering growth.
• Drive an AI-first engineering mindset, identifying opportunities to leverage AI to improve product capabilities, engineering productivity, automation, customer experience, and platform intelligence.
• Bring strong technical leadership across payments, high-volume transaction systems, enterprise B2B platforms, financial workflows, reliability, security, and scalable platform design.
• Establish engineering standards, operating rhythms, accountability, and delivery discipline across the B2B engineering function.
• Partner closely with Architecture, Security, Infrastructure, Data, Product, and Commercial teams to ensure the B2B platform is scalable, secure, maintainable, and aligned to Flywire’s broader technology strategy.
• Recruit, mentor, and develop senior engineering leaders and technical talent, creating a culture of ownership, urgency, collaboration, and high performance.
• Represent B2B engineering in executive-level discussions, providing clear communication on priorities, risks, tradeoffs, delivery timelines, and investment needs.
• Help shape Flywire’s technical brand in Austin and the broader Americas market.

Qualifications

• 15+ years of software engineering experience, including significant leadership experience at Director, Senior Director, or equivalent level.
• Proven experience leading engineering teams in payments, fintech, B2B software, high-volume transaction systems, marketplaces, financial platforms, or enterprise SaaS.
• Strong technical depth in modern backend systems, distributed architecture, APIs, integrations, cloud platforms, reliability, security, and scalable platform design.
• Demonstrated success building or transforming engineering organizations, managing external vendors, and driving high performance-driven engineering culture.
• Experience partnering directly with business, product, and executive stakeholders to define technology strategy and deliver business-critical outcomes.
• Strong understanding of payment flows, financial systems, transaction processing, reconciliation, compliance, risk, or related fintech infrastructure.
• AI-forward mindset, with practical experience applying AI, automation, or data-driven capabilities to improve product and engineering outcomes.
• Experience building engineering culture in a hub or site leadership capacity strongly preferred.
• Ability to operate with executive presence, influence senior stakeholders, and navigate complex organizational dynamics.
• Strong talent magnet with the ability to attract, assess, hire, coach, and retain exceptional engineering talent.
• Excellent communication skills, with the ability to simplify complex technical topics for technical and non-technical audiences.

Location Preference

Austin, Texas. Chicago may also be considered for exceptional candidates.