Sr Benefits Specialist

Flexcar • Boston, MA

3d • $75,000 - $104,000 • Onsite

About The Position

Flexcar is seeking a highly organized and detail-oriented Senior Benefits Specialist to join its Human Resources team. The role owns administration of employee benefits programs, including health, dental, and vision insurance; ancillary insurance; retirement; FSA and commuter programs; family and medical leave; wellness programs; and other internal offerings. The specialist ensures regulatory compliance and provides employees with accurate, responsive benefits support. The position is based onsite in Boston, Massachusetts, is full-time and exempt, and pays $75,000–$104,000, with benefits available from day one.

The role manages enrollment, vendor relationships, benefits billing and reconciliations, HRIS records, employee communications, audits, and leave programs. It also monitors costs, supports budget planning, analyzes benefits data, and stays informed about applicable regulations and industry trends.

Requirements

• 4–6 years of experience in benefits administration.
• Experience with HRIS systems; Rippling is specified.
• In-depth understanding of benefits regulations and compliance, including ERISA, ACA, and HIPAA.
• Experience with monthly billing reconciliation and benefits plan management.
• Strong organizational skills and attention to detail.
• Excellent communication skills and ability to explain complex benefits information clearly.
• Ability to handle sensitive and confidential information professionally.
• Proficiency in Microsoft Office Suite, including Word, SharePoint, and PowerPoint.
• Advanced Excel skills.

Nice To Haves

• Bachelor’s degree in Human Resources, Business Administration, or a related field (preferred).

Responsibilities

• Administer employee benefits programs, including health, dental, and vision insurance; ancillary insurance; retirement; FSA; commuter; family and medical leave; wellness programs; and other internal offerings.
• Manage benefits enrollment for new hires, open enrollment, and qualifying life events.
• Serve as the primary contact for employee benefits inquiries and provide clear, accurate information.
• Ensure compliance with federal, state, and local regulations, including ERISA, ACA, PWFA, HIPAA, and COBRA.
• Maintain accurate benefits election and employee-change records in the HRIS.
• Monitor benefits costs and assist with budget planning.
• Collaborate with external vendors, brokers, and insurance carriers to resolve benefits-related issues.
• Manage EDI and file-transfer setup and monitoring for direct vendor feeds.
• Reconcile monthly benefits vendor billing statements and identify and resolve discrepancies between invoices and internal records.
• Coordinate with Finance to ensure timely processing of benefits-related invoices.
• Maintain records of billing discrepancies and adjustments.
• Help create and communicate benefits materials for employees.
• Schedule and host employee benefits information sessions.
• Analyze benefits data to identify trends and opportunities to improve program offerings.
• Support benefits audits and open enrollment activities.
• Stay informed about benefits regulations, laws, and industry trends to ensure compliance.
• Coordinate and manage leave-of-absence programs, including short-term disability, long-term disability, and Paid Family and Medical Leave (PFML).
• Ensure compliance with federal and state leave laws, including FMLA, PWFA, and ADA.

Benefits

• Flexible PTO policy.
• 401(k) plan with company match from day one.
• Day-one access to low-cost medical, dental, and vision coverage.
• Discounted employee rate on Flexcar products and no annual membership fee.
• Weekly pay.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior