Director, Technology & Analytics

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.

This is not a traditional HR Operations leadership role. 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.

Own Flywire's Global People Technology Strategy

• Develop and execute the long-term roadmap for HR technology, automation, integrations, and digital transformation.
• Serve as the business owner for Workday HCM and the broader People technology ecosystem.
• Partner with IT to establish scalable architecture, governance, security, integrations, and platform optimization.
• Evaluate emerging technologies that improve operational efficiency and employee experience.

• Build an industry-leading People Analytics capability that enables executive decision making.
• Develop dashboards and KPIs across recruiting, workforce planning, retention, engagement, organizational health, performance, and talent development.
• 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.
• Drive simplification, automation, standardization, and scalability across the employee lifecycle.
• Partner with functional leaders to identify opportunities for operational excellence.
• Balance best practices with Flywire's unique culture, business model, and operating principles.

• Lead complex cross-functional transformation initiatives across HR, Finance, IT, and business functions.
• Build strong executive partnerships while effectively influencing without direct authority.
• Develop change management strategies that ensure successful adoption of new capabilities.
• Identify organizational risks and proactively elevate issues while driving practical solutions.

• Chief People Officer
• Talent Acquisition
• HR Business Partners
• Compensation & Benefits
• Finance
• IT
• Security
• Legal
• Executive Leadership Team

• Build governance frameworks for People technology initiatives.
• Improve operational metrics through automation and continuous improvement.
• Create documentation, standards, and scalable operating procedures.
• Develop future roadmaps aligned to business growth.

• 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.
• Demonstrated success leading cross-functional transformation initiatives.
• 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.
• Experience building executive dashboards and workforce analytics.
• Strong knowledge of organizational design, workforce planning, and HR data governance.

• Brings executive presence and credibility.
• Is highly collaborative without sacrificing accountability.
• Knows when to challenge assumptions and when to build consensus.
• Can influence through relationships rather than hierarchy.
• Thinks strategically while remaining execution oriented.
• Simplifies complexity.
• Builds trust quickly.
• Leads through ambiguity.
• Operates with urgency while maintaining quality.
• Understands that successful transformation requires adoption, not simply implementation.

• 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.

This leader will play a critical role in shaping the future of Flywire's People organization by creating technology-enabled experiences that empower employees, improve…