Supervisor, Benefits jobs in United States
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Rakuten · 1 month ago

Supervisor, Benefits

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, as well as comprehensive management of US leave of absence and workplace accommodation processes, while supervising a benefits specialist and leading continuous improvement within US benefits.

E-CommerceElectronicsFinTechInternetPayments

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 knowledgeWorkday proficiencyVendor managementOpen enrollment experienceExcel skillsJudgmentCommunication skillsConfidentiality

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; SHRM-SCP or CEBS certification preferred
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

Preferred

SHRM-SCP or CEBS certification

Benefits

Discretionary bonus
Health
Vision
Dental insurance
401k matching
PTO
Volunteer Time Off (VTO)
Other employee benefits

Company

Rakuten is a provider of e-commerce, fintech, digital content, and communications products and services.

Funding

Current Stage
Public Company
Total Funding
$7.27B
Key Investors
Japan Post Holdings
2025-10-17Post Ipo Debt· $546.3M
2024-12-05Post Ipo Debt· $550.22M
2024-04-04Post Ipo Debt· $1.98B

Leadership Team

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Mickey Mikitani
Founder, Chairman & CEO
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K
Kentaro Hyakuno
Director, Executive Vice President & COO
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Company data provided by crunchbase