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Rakuten International · 1 day ago

Supervisor, Benefits

United States

Full-time

Remote

Mid, Senior Level

$83K/yr - $143K/yr

7+ years exp

Rakuten International is a division of Rakuten Group, Inc., a Japanese global technology leader in services that empower individuals, communities, businesses and society. This role owns day-to-day operations for health & welfare and retirement programs, supervises a benefits specialist, and leads continuous improvement within US benefits.

E-CommerceInternetSoftwareVirtual Reality

Responsibilities

Oversee daily administration of US health & welfare plans (medical, dental, vision, HSA/FSA/Commuter, life & disability, voluntary benefits, EAP, well-being) and 401(k), ensuring accuracy, timeliness, and exceptional service

Lead the comprehensive administration of US leave of absence and workplace accommodation requests (including ADA, FMLA, multi-state leave programs, and company leave programs), ensuring strict compliance, accuracy, timeliness, and empathetic support to employees, in close partnership with relevant stakeholders

Serve as escalation point for complex employee cases; research, resolve, and prevent recurrence through SOPs and training

Manage eligibility, life event processing, evidence of insurability workflows, and coordination of care/case management with carriers

Partner with Payroll to ensure accurate, timely deductions and arrears reconciliation; resolve discrepancies and over/under-collections

Lead annual open enrollment execution end-to-end: project plan, system configuration/UAT, rates, communications, training, and day-of support

Partner with our benefits and retirement brokers to manage day-to-day performance of carriers, TPAs, retirement recordkeeper, leave vendor, and COBRA administrator; own SLAs, escalations, and root-cause corrective actions

Support Director and Global Total Rewards Team on renewals, plan design changes, and RFPs; lead implementations and file feed/EDI changes in partnership with HRIS and vendors

Support People Experience Team on management and administration of the global well-being program

Reconcile and approve monthly invoices; track credits, performance guarantees, and well-being incentives

Ensure compliance with all federal and state regulations pertaining to leave of absences and workplace accommodations, including FMLA, ADA, and relevant state-specific laws. Proactively identify potential risks and partner with Legal/Compliance as needed to mitigate them

Ensure compliance with ERISA, ACA, HIPAA, COBRA, Section 125, MHPAEA, and applicable state regulations; partner with Legal/Compliance as needed

Coordinate annual notices, SPDs/SMMs, SBCs, and 1095-C support with HRIS/Payroll

Manage retirement plan operations in partnership with the recordkeeper and Payroll. Provide ADP/ACP testing support, audits, Form 5500 inputs, loan/hardship reviews, QDROs, and fiduciary calendar tracking

Maintain accurate plan documents and internal SOPs; monitor legislative changes and recommend updates

Own benefit configurations and testing in Workday in partnership with HRIS

Develop dashboards and insights (enrollment, cost trends, participation, well-being utilization, leave interactions, retirement savings health)

Forecast and track benefits budget; identify cost/savings opportunities without compromising employee experience

Supervise a benefits specialist and provide day-to-day guidance, work allocation, and QA; coach for performance and growth

Partner closely with People Experience, HRBPs, Talent Acquisition, Global Total Rewards, Payroll, Finance, Legal, and Communications; deliver clear, inclusive employee communications and manager enablement

Drive process improvement and automation; simplify the benefits experience and reduce escalations

Lead benefits workstreams for new programs, vendor transitions, M&A, site openings, and state expansions

Manage project plans, risks, and stakeholders; deliver on time and within scope

Qualification

US benefits experienceERISA knowledgeADA complianceWorkday proficiencyVendor managementOpen enrollment experienceExcel skillsCommunication skillsLeadership skillsProject management

Required

7-10 years of progressive US benefits experience across health & welfare, retirement, and leave of absence with at least 2 years in a senior/lead capacity guiding others' work

Bachelor's degree in Human Resources, Business Administration, or a related field

Deep working knowledge of ERISA, ACA, COBRA, HIPAA, Section 125, FMLA, and multi-state requirements; experience with ADP/ACP testing support and retirement plan operations

Demonstrated experience managing workplace accommodation requests under the ADA and relevant state laws, including the interactive process and reasonable accommodation determinations

Strong understanding of the interplay between leave of absence laws (e.g., FMLA, state leaves) and workplace accommodation requirements (e.g., ADA)

Hands-on experience running open enrollment, vendor implementations, EDI/file feeds, and invoice reconciliation

Proficiency with HRIS/benefits administration in Workday and strong Excel skills (pivot tables, lookups)

Demonstrated vendor management and negotiation skills; confident navigating escalations and driving SLA accountability

Excellent judgment, confidentiality, and communication skills