Senior Director of B2B Engineering, Flywire
Americas Site Lead
$250-350k
Global payments processing
Be an early applicant
Global payments processing
1001+ employees
Be an early applicant
$250-350k
1001+ employees
Company mission
To improve the payment experience for everyone.
Role
Who you are
- 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
- 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 the job involves
- 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
- 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
- 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
Our take
Flywire is a digital platform that simplifies the paying experience for international transactions. Flywire leverages its vertical-specific software and payments technology to deeply embed within client's existing accounts-receivable workflows.
Flywire was first set up to help international students pay their tuition for American colleges, but has since grown into a global payments enablement and software company. It has processed billions of dollars in payments for clients across the world and secured approval for its major payment institution license, enabling it to operate domestic money transfer and cross-border money transfer services.
Flywire serves clients across education, healthcare, travel, and B2B, including several Ivy League schools, and top US hospital systems. The company appears to be focussed on growth, including by strategic acquisitions and entry into new markets, recently in the Asia Pacific and Australia, as well as further developing its channel partners ecosystem.
Steph
Company Specialist at Welcome to the Jungle
Insights
12% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Mar 2021
$60m
SERIES F
Feb 2020
$120m
SERIES E
Total funding: $323.2m
Company HQ
Downtown Crossing, Boston, MA
Leadership
Mike Massaro
(CEO)Mike joined Flywire as a VP of Business Development in 2012 before becoming CEO in 2013. Prior to this, he spent 6 years at Carrier IQ as a VP of Strategic Accounts & Corporate Development and Advisor.
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