Director, People Strategy & Planning at Flywire

Boston, Massachusetts, United States -

Full Time

Start Date

Immediate

Expiry Date

19 May, 26

Salary

170000.0

Posted On

18 Feb, 26

Experience

10 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

People Strategy, Operating Rhythm, Goal Setting, Cross-functional Coordination, Executive Enablement, Data-driven Insights, Change Management, Stakeholder Management, Influence Without Authority, High-growth Environment, HR Transformation, AI Fluency, Workforce Planning, Executive Writing, Google Workspace, Analytical Acumen

Industry

Software Development

Description

Company Description Are you ready to trade your job for a journey? Become a FlyMate! Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we’re on a mission to deliver the world’s most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world. What more do we need to truly be unstoppable? Perhaps, that is you! Who we are: 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 4,800 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. Job Description 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. Key Responsibilities People Strategy, Planning, and Operating Rhythm 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. Business Operations and Executive Enablement 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. Culture and Global Engagement 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. Stakeholder Management and Influence 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. Qualifications Here's what we're looking for 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. Technologies We Use Workday, Lattice, Jira, SmartRecruiters Google Workspace and collaboration tools Presentation and data visualization tools Additional Information What We Offer: 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 Submit today and get started! We are excited to get to know you! Throughout our process you can expect to meet different FlyMates including the Hiring Manager, other Flymates, the department VP, and participate in a skills assessment. Your Talent Acquisition Partner will walk you through the steps and be your “go-to” person for questions. Flywire is an equal opportunity employer. With over 40 nationalities across 12 different offices, and diversity and inclusion at the core of our people agenda, we believe our FlyMates are our greatest asset, and we’re excited to watch our unique culture evolve with each new hire. The US base salary range for this full-time position is $150,000 - 170,000 plus restricted stock units and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training. #LI-Hybrid

Responsibilities

This role acts as the People organization’s central integrator, connecting strategy to execution across all People functions and serving as a strategic thought partner to the Chief People Officer. Key duties involve driving the annual and quarterly planning cycles, managing leadership meeting cadences, and owning high-impact transformation projects.