Sr Benefits Specialist

Flexcar • Boston, MA

1d • 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; commuter programs; family and medical leaves; wellness programs; and other internal offerings. The specialist ensures regulatory compliance and provides employees with responsive, accurate benefits support.

The position manages enrollment, employee inquiries, vendor relationships, benefits billing and reconciliations, benefits communications, and leave of absence programs. It also supports audits and open enrollment, analyzes benefits data, monitors costs, and stays informed about regulatory requirements and industry trends. The role is onsite in Flexcar’s Boston office and is full-time, exempt, with a listed salary range of $75,000–$104,000.

Requirements

• 4–6 years of experience in benefits administration.
• Experience with HRIS systems; Rippling is identified.
• In-depth understanding of benefits regulations, including ERISA, ACA, and HIPAA, and related compliance.
• Experience with monthly billing reconciliation and benefits plan management.
• Strong organizational skills and attention to detail.
• Excellent communication skills, including the 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 proficiency.

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 programs; family and medical leaves; 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 applicable 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 ensure accuracy.
• Identify and resolve discrepancies between vendor invoices and internal records.
• Coordinate with Finance to ensure timely processing of benefits-related invoices.
• Maintain records of discrepancies and adjustments.
• Assist in creating and communicating benefits materials for employees.
• Schedule and host benefits information sessions for employees.
• 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 leaves of absence, 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 medical, dental, and vision coverage described as excellent and low-cost.
• Discounted employee rate on Flexcar products and no annual membership fee.
• Weekly pay.

What This Job Offers

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