Director, People Strategy & Planning

Flywire • Boston, MA

7h • Hybrid

About The Position

The Opportunity
We are seeking a Director-level individual contributor to serve as the People organization’s central integrator, connecting strategy to execution across People Operations, Talent, Total Rewards, People Partners, and executive stakeholders.

This role serves as a strategic thought partner to the Chief People Officer, responsible for orchestrating the operating rhythm, driving priorities, and ensuring the People function operates with enterprise-grade rigor, clarity, and follow-through. While this role does not have direct people management responsibility, it plays a critical role in aligning cross-functional stakeholders and enabling execution across the business.

Requirements

• 10+ years of experience in People Operations, Business Operations, Strategy, Consulting, or a Chief of Staff-type role within a high-growth, enterprise-scale technology company.
• Demonstrated experience supporting C-level executives and senior leadership teams in highly complex, fast-moving environments.
• Ability to translate complex data into clear, actionable narratives for executive and board audiences.
• Proven HR transformation experience, including leading or materially contributing to large-scale People initiatives such as organizational redesign, operating model evolution, process modernization, or systems implementation across a global environment.
• AI fluency and applied experience leveraging AI tools and automation within People functions, including workforce planning, analytics, workflow optimization, and executive enablement.
• Experience building and operationalizing dashboards and analytics, including workforce metrics, headcount planning, talent insights, and executive-level reporting.
• Exceptional communication and executive level writing skills along with experience building executive-level materials and navigating board-level or executive forums.
• Deep expertise in Google Workspace, including advanced use of Google Slides, Sheets, Docs, and collaboration tools to build executive-ready materials, dynamic dashboards, planning models, and structured operating workflows.
• Strong financial and analytical acumen, with experience partnering on budgeting, headcount planning, or workforce strategy.
• Agile mindset with a track record of experimentation and iteration to drive transformation.
• Exceptional stakeholder management skills, with the ability to balance diplomacy, clarity, and firmness.
• High tolerance for ambiguity, paired with a strong instinct for bringing structure and order to complex systems.
• Global mindset with experience working across regions, time zones, and cultures.

Responsibilities

• Partner closely with the Chief People Officer to translate People strategy into clear priorities, operating plans, and execution roadmaps across the People Leadership Team.
• Drive annual and quarterly People planning cycles, including goal setting, prioritization, sequencing, and progress tracking across all People sub-functions.
• Act as the central point of coordination for leadership meetings, leader syncs, and cross-functional People initiatives, ensuring agendas, materials, decisions, and follow-ups are tightly managed.
• Streamline internal processes and workflows across the people team to enable effective communication and collaboration.
• Own and lead team-wide transformation projects and other high–impact initiatives.
• Serve as a strategic and operational thought partner to the CPO, anticipating needs, pressure-testing plans, and acting as a proxy in select forums when appropriate.
• Prepare high-quality, executive-level materials including board-ready presentations, operating updates, strategy decks, and written narratives.
• Support complex executive workflows, including sensitive leadership discussions, organizational changes, and confidential initiatives while ensuring alignment and execution on agreed upon deliverables.
• Craft narratives for executive messaging that drives clarity, increases adoption and showcases business impact of people team programs and the alignment to enterprise goals.
• Unlock strategic decision making through data-driven insights and recommendations. Leverage analytics to maintain tracking of key metrics, assess trends and measure effectiveness.
• Introduce and evaluate emerging technologies and translate them into practical, value-driving use cases for the People organization.
• Design effective change management approaches that incorporate data and engaging messaging that drive employee engagement.
• Partner with our Places team and regional leaders to support thoughtful office-based experiences, including leadership visits, onboarding touchpoints, and cultural integration.
• Help shape consistent expectations around in-office engagement, collaboration, and cultural fit across regions, even for team-of-one or remote-adjacent roles.
• Balance global consistency with regional nuance, ensuring Flywire’s culture evolves without losing its essence as we adapt people programming to support scaling and growth.
• Build strong, trusted relationships across the People Leadership Team, Executive Team, Finance, Legal, Product, Engineering, and other key stakeholders.
• Influence without authority by bringing structure, data, and sound judgment to complex, ambiguous situations.

Benefits

• Competitive compensation, including Restricted Stock Units
• Employee Stock Purchase Plan (ESPP)
• Flying Start, our immersive global induction program
• A dynamic, highly collaborative global team
• Wellbeing programs supporting mental and physical health
• Competitive time off, including FlyBetter Days and Digital Disconnect Days
• Ongoing learning and development opportunities
• The opportunity to make a meaningful, visible impact at a global, public-company-scale organization

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed