Sr Benefits Specialist

Flexcar • Boston, MA

2d • $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 leaves; 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 offers a salary of $75,000–$104,000 plus benefits from day one.

Requirements

• 4–6 years of experience in benefits administration.
• Experience with HRIS systems, specifically Rippling.
• 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 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 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 and 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 federal, state, and local regulations, including ERISA, ACA, PWFA, HIPAA, and COBRA.
• Maintain accurate benefits elections and employee-change records in the HRIS.
• Monitor benefits costs and assist with budget planning.
• Collaborate with 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 discrepancies against internal records.
• Work 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 benefits information sessions.
• Analyze benefits data to identify trends and opportunities to improve program offerings.
• Support benefits audits and open-enrollment activities.
• Stay current on benefits regulations, laws, and industry trends.
• Coordinate and manage leave-of-absence programs, including short-term disability, long-term disability, and Paid Family and Medical Leave.
• 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
• Education Level: No Education Listed