Senior Director, B2B Engineering, Site Lead

Flywire

Confirmed live yesterday High trust
Hybrid

Quick summary

Work type
Hybrid
Location
Austin, TXChicago, IL
Posted
1 day ago
Freshness
Confirmed live yesterday

Market check

Salary context

How this pay compares to similar roles

Similar $220k
$154k most similar roles pay here $281k

This listing doesn't post a salary. Most similar roles pay $177,250–$263,250.

Based on 240 similar postings.

Employer

About Flywire

Flywire is a global payments enablement and software company specializing in high-stakes, complex payment verticals including education, healthcare, travel, and B2B, processing international payments across 240 countries. Industry: Financial Technology & Global Payments

Flywire currently has 13 open roles on FindRole.

Listed pay typically runs $95,500–$110,500 across 10 roles with salary data.

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At a glance

TL;DR · Senior Director, B2B Engineering, Site Lead

The Senior Director, B2B Engineering, Americas Site Lead joins the engineering organization to lead technical strategy, architecture, and execution for the B2B business. This leader is responsible for building a high-performing internal team, establishing Austin as a strategic technology hub, and driving an AI-first engineering mindset to improve product capabilities and productivity. The role involves managing high-volume transaction systems, enterprise integrations, financial workflows, and scalable platform design while ensuring security and reliability across the B2B platform. Key competencies include expertise in payment flows, transaction processing, reconciliation, and compliance within fintech infrastructure. The successful candidate will navigate complex organizational dynamics to define technology roadmaps, mentor senior technical talent, and establish engineering standards. This position addresses the challenge of scaling a global payments platform by transitioning capabilities from external contractors to internal teams while fostering a culture of ownership.

What you'll do

  • Own the technical strategy, architecture, and execution for Flywire’s B2B engineering organization.
  • Establish Austin as a strategic technology hub by serving as the Americas engineering site lead.
  • Build and scale an internal engineering team to reduce dependency on external contractors.
  • Drive an AI-first mindset to improve product capabilities, automation, and engineering productivity.
  • Define and deliver the technology roadmap in partnership with Product, Commercial, and Engineering leadership.
  • Establish engineering standards, operating rhythms, and delivery discipline across the B2B function.
  • Recruit, mentor, and develop senior engineering leaders and technical talent.
  • Represent B2B engineering in executive-level discussions regarding priorities, risks, and investment needs.

What we're looking for

  • 15+ years of software engineering experience including significant leadership at the Director or Senior Director level.
  • Proven experience leading teams in payments, fintech, B2B software, high-volume transaction systems, or enterprise SaaS.
  • Strong technical depth in backend systems, distributed architecture, APIs, cloud platforms, and scalable platform design.
  • Demonstrated success building or transforming engineering organizations and managing external vendors.
  • Experience with payment flows, financial systems, reconciliation, compliance, risk, or related fintech infrastructure.
  • AI-forward mindset with practical experience applying AI and automation to improve product and engineering outcomes.
  • Ability to operate with executive presence and influence senior stakeholders across complex organizational dynamics.
  • Experience building engineering culture in a hub or site leadership capacity (preferred).

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