Sr Benefits Specialist

Job Title: Sr Benefits Specialist
Location: Boston, MA (Onsite in office)
Position Type: Full-time – Exempt
Salary: $ 75,000- $104,000 + Benefits Day 1

Who We Are
Flexcar is completely reimagining car ownership. Buying a car is expensive, and leasing locks you in. So, we created a better way: flexing. Flexcar gives people their own car with one monthly payment that includes insurance, maintenance, roadside, and registration, plus the freedom to swap, keep, or return it as life changes. It's more affordable, more flexible, and more enjoyable than buying or leasing. By combining operational expertise with technology, data, and AI, we're transforming every part of the customer journey. We're scaling fast, and we're building the next generation of leaders to scale with us.

What you will do

We are seeking a highly organized and detail-oriented Senior Benefits Specialist to join our Human Resources team. In this role, the Senior Benefits Specialist will own the administration of all employee benefits programs, including Health/Dental/Vision Insurances, Ancillary Insurances, Retirement Program, FSA Program, Commuter Program, Family and Medical Leaves, Wellness Programs, and other internal offerings. You will ensure regulatory compliance and offer exceptional service to employees. The ideal candidate will have a strong understanding of benefits regulations, as well as the ability to manage complex tasks with precision and efficiency.

Key Responsibilities

• Administer employee benefits programs, including Health/Dental/Vision Insurances, Ancillary Insurances, Retirement Program, FSA Program, Commuter Program, Family and Medical Leaves, Wellness Programs, and other internal offerings.
• Manage benefit enrollment for new hires, open enrollment, and qualifying life events.
• Act as the primary contact for employee inquiries regarding benefits, providing clear and accurate information.
• Ensure compliance with federal, state, and local regulations such as ERISA, ACA, PWFA, HIPAA, and COBRA.
• Maintain accurate records in the HRIS for benefits elections and employee changes.
• Monitor benefits costs and assist in 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 feeds with vendors.
• Reconcile monthly billing statements from benefits vendors, ensuring accuracy.
• Identify and resolve discrepancies between vendor invoices and internal records.
• Work with the finance team to ensure timely processing of benefit-related invoices.
• Maintain records of discrepancies and adjustments for future reference.
• Assist with the creation and communication of benefits-related materials for employees.
• Schedule and host benefit informational sessions for employees.
• Analyze benefits data to identify trends and opportunities for improvement in program offerings.
• Support benefits audits and open enrollment activities.
• Stay informed on 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.

What Drives Success for this Role

• Bachelor’s degree in Human Resources, Business Administration, or related field (preferred).
• 4–6 years of experience in benefits administration.
• Experience with HRIS (Rippling) systems.
• In-depth understanding of benefits regulations (ERISA, ACA, HIPAA) and compliance.
• Experience with monthly billing reconciliation and benefits plan management.
• Strong organizational skills and attention to detail.
• Excellent communication skills, with the ability to explain complex benefits information clearly.
• Ability to handle sensitive and confidential information with professionalism.
• Proficiency in Microsoft Office Suite (Word, SharePoint, PowerPoint). Must be an advanced Excel user.

What Tops the Tank

• Rest & Relaxation: Flexible PTO policy.
• Future Savings: Benefit from a 401(k) plan with company match from day one.
• Benefits: Day One - Excellent, low-cost healthcare coverage including medical, dental, vision.
• Drive a Flexcar! Discounted employee rate on Flexcar products and no annual membership fee.
• Weekly pay
• Other amazing opportunities

Flexcar is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. Flexcar provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.