Senior Director, B2B Engineering

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. The Senior Director will own the technology strategy and execution for Flywire’s B2B business, partner closely with Product, Commercial, Operations, and Engineering leadership. This leader will also serve as the engineering site lead for Austin, helping establish Austin as a strategic engineering hub for Flywire. The ideal candidate brings deep experience in payments, high-volume transaction systems, enterprise B2B platforms, and modern engineering practices, with the leadership maturity to operate at senior levels across a complex, global organization.

What You’ll Do

• Lead Flywire’s B2B engineering organization, owning technical strategy, delivery, architecture, execution, and long-term scalability.
• Partner with the CTO, Product, B2B business leaders, and cross-functional stakeholders to 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 processing, enterprise integrations, 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

Here's What We're Looking For

• 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.

What Success Looks Like

In the first 6 to 12 months, this leader will:

• Establish a clear technology strategy and operating model for B2B engineering.
• Build trust and credibility with B2B business leaders, Product, Engineering, and executive stakeholders.
• Begin transitioning critical B2B engineering capability from external contractors to internal Flywire talent.
• Hire and develop a strong core engineering team in Austin or another strategic Americas hub.
• Improve delivery discipline, engineering quality, platform reliability, and technical ownership.
• Identify practical AI-first opportunities that improve product capability, customer value, and engineering productivity.
• Create a strong foundation for Flywire’s Americas engineering site strategy.

Why This Role Matters

Flywire’s B2B business is a strategic growth area, and the technology foundation behind it is critical to our ability to scale. This role is not simply about managing engineers. It is about building the right technical strategy, strengthening internal ownership, modernizing how we deliver, and establishing a senior engineering presence in the Americas that can help shape the next chapter of Flywire’s growth.