Flywire

Flywire

Director, People Technology & Analytics

Boston, MA, United States · Director · Full-time

Sponsorship not specified$145k-$207kDetected 21 days ago
AgileProcess ImprovementRecruitingHRHRISLeadershipCollaboration

About the role

  • This is not a traditional HR Operations leadership role.

Responsibilities

  • Own Flywire's Global People Technology Strategy
  • Develop and execute the long-term roadmap for HR technology, automation, integrations, and digital transformation.
  • Partner with IT to establish scalable architecture, governance, security, integrations, and platform optimization.
  • Lead People Analytics & Workforce Intelligence
  • Build an industry-leading People Analytics capability that enables executive decision making.
  • Optimize Global People Processes
  • Drive simplification, automation, standardization, and scalability across the employee lifecycle.
  • Partner with functional leaders to identify opportunities for operational excellence.
  • Drive Enterprise Transformation
  • Lead complex cross-functional transformation initiatives across HR, Finance, IT, and business functions.

Requirements

  • 10+ years of progressive experience leading HR Technology, People Systems, People Analytics, HRIS, or Digital HR Transformation.
  • Experience leading enterprise HR technology implementations, preferably Workday.
  • Strong understanding of global HR operations and end-to-end People processes.
  • Experience partnering with executive leadership.
  • Proven ability to influence stakeholders across multiple business functions.
  • Experience managing complex vendor relationships and technology roadmaps.

Nice to have

  • Experience supporting publicly traded global organizations.
  • Experience working across multiple international regions.
  • Familiarity with Agile delivery methodologies.
  • Knowledge of AI-enabled HR technologies and automation platforms.
  • Experience leveraging predictive analytics and workforce intelligence.
  • Master's degree in Business, Information Systems, Human Resources, Organizational Development, or related discipline preferred.
  • Why This Role Matters
  • The ideal candidate understands that great People Technology is not simply about implementing systems.

Compensation

  • $145k-$207k

Benefits

  • Develop dashboards and KPIs across recruiting, workforce planning, retention, engagement, organizational health, performance, and talent development.
  • Compensation & Benefits

Company info

  • Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education.
  • We've since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.
  • Today we support more than 5,100 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.
  • With over 1,200 global FlyMates, representing more than 40 nationalities, and in 12 offices world-wide, we're looking for FlyMates to join the next stage of our journey as we continue to grow.
  • The Opportunity
  • Flywire is seeking an experienced Director, People Technology & Analytics to lead the strategy, optimization, and evolution of our global People technology ecosystem and workforce analytics function.
  • Reporting to the Chief People Officer, this leader will serve as the strategic owner for HR technology, people data, reporting, process optimization, automation, and digital transformation initiatives that enable a world-class employee experience while supporting Flywire's continued global growth.
  • Instead, you'll partner closely with stakeholders across Talent Acquisition, People Business Partners, Total Rewards, Payroll, Finance, IT, Security, Legal, and executive leadership to build scalable technology solutions, modernize workflows, improve decision making through analytics, and deliver operational excellence across the employee lifecycle.
  • Success in this role requires someone who combines deep expertise in People systems with a sophisticated understanding of end-to-end HR processes, exceptional business partnership skills, executive presence, and the ability to influence change across a rapidly evolving global organization.
  • Serve as the business owner for Workday HCM and the broader People technology ecosystem.
  • Evaluate emerging technologies that improve operational efficiency and employee experience.
  • Translate workforce data into strategic business insights for executive leadership.
  • Establish governance around data quality, reporting accuracy, and metric standardization.
  • Evaluate existing People processes and redesign them using technology-first thinking.
  • Balance best practices with Flywire's unique culture, business model, and operating principles.
  • Identify organizational risks and proactively escalate issues while driving practical solutions.
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This listing is sourced directly from Flywire's careers page and normalized into a canonical job model.