4-6 years of experience in benefits administration and payroll
Solid knowledge of federal and state benefits, leave, and payroll regulations
Experience with Rippling (strongly preferred) and payroll software; NetSuite a plus
Advanced Excel skills
Experience with monthly billing reconciliation and benefits plan management
Strong attention to detail and clear communication
Bachelor's degree in HR, Business, or a related field preferred
Responsibilities
Administer all benefits programs including medical, dental, vision, and 401(k)
Manage enrollment for new hires and qualifying life events
Serve as the primary resource for employee benefits questions
Keep benefits data accurate and up to date in Rippling
Set up and monitor EDI and file-transfer feeds with carriers
Coordinate STD, LTD, and FMLA leaves from request to return to work
Reconcile monthly vendor invoices against internal records
Help process weekly payroll for hourly employees and resolve discrepancies
Create benefits guides and host employee information sessions
Maintain compliance with ERISA, ACA, HIPAA, and other regulations
Benefits
Medical, dental, and vision coverage starting day one
401(k) with company match from day one
Flexible PTO
Weekly pay
Full Job Description
Sr. Benefits Specialist
Location: Boston, MA or San Jose, CA (onsite) Type: Full-time, Exempt Compensation: $115K-$130K + bonus incentive | Full benefits from day one
We're looking for a Sr. Benefits Specialist to own employee benefits programs from start to finish and support weekly payroll for a growing US workforce. Sitting between HR and Finance, you'll be the go-to expert for employees, the main contact for brokers and carriers, and the person who keeps programs accurate, compliant, and easy to understand. This role suits someone who is precise, comfortable with regulations, and good at explaining complex topics simply. What You'll Do
Benefits Administration
Administer all benefits programs: medical, dental, vision, ancillary insurance, 401(k), FSA, commuter, wellness, and leave
Manage enrollment for new hires, qualifying life events, and annual open enrollment
Serve as the primary resource for employee benefits questions
Keep benefits data in Rippling accurate and up to date
Set up and monitor EDI and file-transfer feeds with carriers and vendors
Partner with brokers, carriers, and vendors to resolve issues
Track benefits costs and utilization trends, and provide input on budget planning
Leave of Absence
Coordinate STD, LTD, Massachusetts PFML, and FMLA leaves from request through return to work
Manage ADA and PWFA accommodations in partnership with HR and managers
Ensure compliance with federal and state leave laws in every state where the company operates
Billing Reconciliation
Reconcile monthly vendor invoices against internal records, and resolve discrepancies
Work with Finance to make sure invoices are paid on time, and keep clear records of adjustments
Payroll Support
Help process weekly payroll for hourly employees, including overtime and shift differentials
Resolve payroll discrepancies and answer employee questions with the payroll team
Support payroll tax filings and reporting
Prepare payroll journal entries in NetSuite
Communication & Compliance
Create benefits guides and materials, and host employee information sessions
Analyze benefits data to find trends and ways to improve programs
Maintain compliance with ERISA, ACA, HIPAA, COBRA, FMLA, ADA, and PWFA, and support audits
What You Bring
4-6 years of experience in benefits administration and payroll
Solid knowledge of benefits, leave, and payroll regulations at the federal and state levels
Experience with Rippling (strongly preferred) and payroll software; NetSuite a plus
Advanced Excel skills
Experience with monthly billing reconciliation and benefits plan management
Strong attention to detail, discretion with confidential information, and clear communication
Bachelor's degree in HR, Business, or a related field preferred
Bonus points: CBP, CPP, PHR, or SHRM-CP certification; experience in a fast-paced, multi-state organization. Benefits
Medical, dental, and vision coverage starting day one
