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Supervisor, Benefits
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Job Description:
Location: This role is eligible for remote work in CO, CT, FL, GA, IL, MA, TX, WI
Rakuten International is a division of Rakuten Group, Inc., a Japanese global technology leader in services that empower individuals, communities, businesses and society. Headquartered in San Mateo, California with more than 4,000 employees worldwide, the Rakuten International business portfolio includes market leaders in e-commerce, digital marketing, advertising, communications and entertainment. We create products and services that provide exceptional value by aligning members and the businesses that want to engage them in a shared community.
Summary
Rakuten International is seeking a hands-on US Benefits Lead to bridge strategy and execution. 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. The Lead will supervise and guide the work of our benefits specialist, and will be instrumental in leading continuous improvement and innovation within US benefits. The Lead will partner closely with the Director and key stakeholders on renewals, plan design, and vendor performance. The ideal candidate is equally comfortable rolling up their sleeves to resolve complex employee issues and stepping back to optimize processes, data, and vendor outcomes. This role requires a driven individual who is eager to shape and advance Rakuten’s benefits strategy in the US.
What you’ll do:
Program operations and employee support
- 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.
Vendor and plan management
- 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.
Compliance and governance
- 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.
Data, systems, and analytics
- 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.
People leadership and cross-functional partnership
- 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.
Change, projects, and M&A
- 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.
What you’ll bring:
Required qualifications
- 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.
#LI-EP1
Five Principles for Success
Our worldwide practices describe specific behaviors that make Rakuten unique and united across the world. We expect Rakuten employees to model these 5 Shugi Principles of Success.
Always improve, Always Advance - Only be satisfied with complete success - Kaizen
Passionately Professional - Take an uncompromising approach to your work and be determined to be the best
Hypothesize - Practice - Validate – Shikumika - Use the Rakuten Cycle to succeed in unknown territory
Maximize Customer Satisfaction - The greatest satisfaction for our teams is seeing their customers smile
Speed!! Speed!! Speed!! - Always be conscious of time - take charge, set clear goals, and engage your team
Our worldwide practices describe specific behaviors that make Rakuten unique and united across the world. We expect Rakuten employees to model these 5 Shugi Principles of Success.
Always improve, Always Advance - Only be satisfied with complete success - Kaizen
Passionately Professional - Take an uncompromising approach to your work and be determined to be the best
Hypothesize - Practice - Validate – Shikumika - Use the Rakuten Cycle to succeed in unknown territory
Maximize Customer Satisfaction - The greatest satisfaction for our teams is seeing their customers smile
Speed!! Speed!! Speed!! - Always be conscious of time - take charge, set clear goals, and engage your team
Rakuten provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type. Rakuten considers applicants for employment without regard to race, color, religion, age, sex, national origin, disability status, genetic information, protected veteran status, sexual orientation, gender, gender identity or expression, or any other characteristic protected by federal, state, provincial or local laws.
At the time of posting, Rakuten expects the base compensation for this role to be within the range shown below. Individual compensation will vary based on job-related factors, including the skills, qualifications, and experience of the successful candidate as well as business need and geographic location. The successful applicant for this role will be eligible for discretionary bonus, health, vision, dental insurance, 401k matching, PTO, Volunteer Time Off (VTO), and other employee benefits as the company implements.
USD $82,782.00 - $142,992.00 annuallySimilar jobs
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