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Flywire is seeking a Senior Director of B2B Engineering to lead and scale the engineering organization across the Americas, with a primary base in Austin, Texas. This is a critical leadership role at the intersection of engineering strategy, payments innovation, AI-first product development, and site leadership.
You will own the technology strategy and execution for Flywire's B2B business, a strategic growth area. You'll partner closely with the CTO, Product, Commercial, Operations, and Engineering leadership to define and deliver the technology roadmap. You'll also serve as the engineering site lead for Austin, helping establish it as a strategic engineering hub for Flywire.
Key responsibilities include:
- Leading Flywire's B2B engineering organization, owning technical strategy, delivery, architecture, execution, and long-term scalability
- Building and scaling a high-performing internal engineering team, reducing dependency on external contractors and strengthening internal IP and technical depth
- Serving as the Americas engineering site lead and creating the foundation for future engineering growth
- Driving an AI-first engineering mindset, identifying opportunities to leverage AI to improve product capabilities, engineering productivity, automation, customer experience, and platform intelligence
- Bringing strong technical leadership across payments, high-volume transaction processing, enterprise integrations, financial workflows, reliability, security, and scalable platform design
- Establishing engineering standards, operating rhythms, accountability, and delivery discipline
- Partnering with Architecture, Security, Infrastructure, Data, Product, and Commercial teams to ensure the B2B platform is scalable, secure, maintainable, and aligned to broader technology strategy
- Recruiting, mentoring, and developing senior engineering leaders and technical talent
- Representing B2B engineering in executive-level discussions with clear communication on priorities, risks, tradeoffs, and investment needs
- Helping shape Flywire's technical brand in Austin and the broader Americas market
In the first 6-12 months, success looks like establishing a clear technology strategy and operating model for B2B engineering, building trust with business and product leaders, transitioning critical B2B engineering capability from external contractors to internal talent, hiring and developing a strong core engineering team, improving delivery discipline and platform reliability, identifying practical AI-first opportunities, and creating a strong foundation for Flywire's Americas engineering site strategy.
Flywire is a global payments enablement and software company supporting over 5,100 clients across education, healthcare, travel, and B2B industries, with operations in 12 offices worldwide and over 1,200 employees representing 40+ nationalities.
REQUIREMENTS:
- 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 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 be considered for exceptional candidates)
