Benefits / Payroll Manager
Flexcar • Boston, Massachusetts • Full Time
Posted on Thu, Jun 25, 2026
Location: Boston, MA (Onsite in office) 5 days 50 hours week
Position Type: Full-time – Exempt
Salary: $115K - $130K + Bonus Incentive and Full Benefit Package Day One
Who We Are:
Flexcar is completely reimagining car ownership. We offer the world’s first month-to-month car lease, with insurance and maintenance included. By combining operational expertise with technology, data, and AI, we are transforming every aspect of the customer journey and providing a smarter, more flexible alternative to traditional ownership.
We’re scaling fast — and we’re building the next generation of leaders to scale with us.
Job Summary:
We are seeking a highly organized and detail-oriented Benefits/Payroll Manager to join our Human Resource and Finance team. In this role, the Benefits/Payroll Manager 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, offer exceptional service to employees, and support weekly payroll processing for all US team members. The ideal candidate will have a strong understanding of benefits and compensation regulations, as well as the ability to manage complex tasks with precision and efficiency.
Key Responsibilities:
Benefits Administration:
- 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 set up and monitoring for direct feeds with vendors
Payroll Support
- Assist with processing payroll for nonexempt (hourly) employees, ensuring accuracy and timely payment.
- Ensure proper calculation of work hours, overtime, shift differentials, and other variables.
- Collaborate with the payroll team to resolve discrepancies and employee inquiries.
- Maintain accurate records of payroll adjustments, ensuring compliance with labor laws.
- Support the preparation and filing of payroll taxes and reports.
- Prepares and processes payroll journal entries in NetSuite, ensuring accurate recording of wages, taxes, and deductions to the general ledger
Monthly Billing Reconciliation:
- 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.
Additional Responsibilities:
- 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 and payroll processing
- Knowledge of payroll processing and federal/state payroll regulations.
- Experience with HRIS (Rippling) systems and payroll software.
- 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 and payroll information clearly.
- Ability to handle sensitive and confidential information with professionalism.
- Proficiency in Microsoft Office Suite (Word, SharePoint, PowerPoint). Must be advanced Excel user.
Preferred Skills:
- Certifications such as CBP, CPP, PHR, or SHRM-CP.
- Experience in a fast-paced, multi-state organization.
- Knowledge of state-specific payroll and benefit requirements.
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.