Senior People Operations Specialist

Flywire • Boston, MA

1d • Hybrid

About The Position

The Senior Specialist, People Operations is responsible for delivering accurate, compliant execution of employee lifecycle processes globally, with primary operational ownership across the Americas region (US, Canada, and Mexico), while operating against defined service levels in a high-volume environment. This role acts as the operational nexus for data integrity, process consistency, and audit readiness within Workday and related People systems. Operating with a high degree of autonomy, the individual manages complex cases, enforces standards, mitigates risks, and advances process improvements, leveraging automation and AI-enabled solutions to enhance efficiency, strengthen service delivery, and enable the function to operate at greater scale and impact.

Requirements

• 5–7 years in People Operations / HR Operations, including advanced hands-on experience with Workday transactions, data governance, and reporting
• Proven track record managing complex and exception-based employee lifecycle cases
• Experience operating within a controlled, audit-driven environment (SOX exposure preferred)
• Demonstrated experience driving process improvements, automation, or system optimisation, including the use of AI-enabled tools to reduce manual effort and improve accuracy
• Working knowledge of labor laws and compliance requirements across the US (including FLSA/EEO), Canada, and Mexico
• High precision and attention to detail, with a strong control and audit mindset
• Effective execution in high-volume, high-risk operational environments
• Sound judgment and problem-solving in determining when to execute, escalate, or route matters
• Clear, concise communication and effective collaboration across cross-functional stakeholders

Responsibilities

• Execute end-to-end employee lifecycle transactions (hires, changes, terminations), ensuring accuracy, timeliness, and proper documentation in Workday
• Maintain consistency and standardisation across lifecycle processes within the Americas region
• Independently manage complex and non-standard cases, including policy and system exceptions
• Support operational activities related to employee mobility, including system transactions, documentation, and process coordination in partnership with the Global Mobility team
• Own the accuracy, completeness, and integrity of employee data within Workday as the system of record
• Ensure employee data impacting downstream processes (e.g. payroll, compensation, reporting, benefits) is accurate, complete, and timely
• Identify and resolve data discrepancies before downstream impact (payroll, reporting, compliance)
• Partner with Payroll, Finance, and other stakeholders to investigate and resolve data-related issues
• Execute and validate compensation-related transactions with strict adherence to data accuracy and process controls
• Support regional benefits programs in partnership with the Global Benefits COE and external vendors, ensuring accurate system configuration and alignment of employee data in Workday
• Execute People policies and procedures with precision, ensuring consistent application across jurisdictions
• Maintain strong working knowledge of labor laws and regulatory requirements across the Americas region
• Perform quality assurance checks on transactions and documentation to ensure adherence to defined standards
• Act as a key control layer for People processes, ensuring accuracy, consistency, and compliance
• Serve as an escalation point for complex operational matters and high-risk employee lifecycle transactions across the region
• Support regional and global internal and external audits (including SOX) through accurate and well-maintained records
• Identify systemic risks, control gaps, and operational inconsistencies, driving corrective actions and sustainable resolution
• Analyse root causes of recurring issues and implement scalable process enhancements
• Drive workflow optimisation initiatives to reduce manual effort, improve throughput, and strengthen service delivery
• Leverage system capabilities and AI-enabled solutions to improve efficiency, accuracy, and user experience
• Partner with Global People and cross-functional teams to ensure coordinated execution of employee lifecycle activities
• Act as a key point of contact for employee lifecycle inquiries, ensuring timely resolution or appropriate routing to specialist teams
• Contribute to regional and global initiatives that strengthen People Operations scalability, effectiveness, and consistency
• Provide guidance and quality oversight across complex cases and regional processes

Benefits

• Competitive compensation
• Employee Stock Purchase Plan (ESPP)
• Competitive time off, including Digital Disconnect and FlyBetter Days to volunteer in a cause you believe in.
• Work with brilliant people globally
• Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates
• Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers, OneFlywire Career Mobility)

What This Job Offers

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