Senior People Operations Specialist, Flywire
$80-90k
Global payments processing
Be an early applicant
Global payments processing
1001+ employees
Be an early applicant
$80-90k
1001+ employees
Company mission
To improve the payment experience for everyone.
Role
Who you are
- 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
What the job involves
- 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
- 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
- What Success Looks Like;
- Consistently high data accuracy with minimal error rates across transactions
- Strong audit outcomes with fully compliant, well-documented processes
- Effective handling of complex and exception cases with minimal escalation
- Measurable improvements in process efficiency and reduction in manual effort
- Minimal downstream errors attributable to upstream data inaccuracies
Our take
Flywire is a digital platform that simplifies the paying experience for international transactions. Flywire leverages its vertical-specific software and payments technology to deeply embed within client's existing accounts-receivable workflows.
Flywire was first set up to help international students pay their tuition for American colleges, but has since grown into a global payments enablement and software company. It has processed billions of dollars in payments for clients across the world and secured approval for its major payment institution license, enabling it to operate domestic money transfer and cross-border money transfer services.
Flywire serves clients across education, healthcare, travel, and B2B, including several Ivy League schools, and top US hospital systems. The company appears to be focussed on growth, including by strategic acquisitions and entry into new markets, recently in the Asia Pacific and Australia, as well as further developing its channel partners ecosystem.
Steph
Company Specialist at Welcome to the Jungle
Insights
12% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Mar 2021
$60m
SERIES F
Feb 2020
$120m
SERIES E
Total funding: $323.2m
Company HQ
Downtown Crossing, Boston, MA
Leadership
Mike Massaro
(CEO)Mike joined Flywire as a VP of Business Development in 2012 before becoming CEO in 2013. Prior to this, he spent 6 years at Carrier IQ as a VP of Strategic Accounts & Corporate Development and Advisor.
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