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 • 401(k) with company match from day one • Flexible PTO • Weekly pay Equal Opportunity Employer.