Senior Benefits Specialist

RiverPark Ventures; New York (NY); On-site; USD 80,000 - 90,000; Full time

Benefits offered by this job

Comprehensive health coverage

401(k) with generous match

Parental leave and extended leave

PTO 20 days

Dental and vision plans

Mental health and wellness perks

Job summary

Via is on a mission to transform public transportation through data-driven, efficient digital networks. Via seeks a Senior Benefits Specialist to oversee US and global health, welfare, retirement and wellness programs, ensuring regulatory compliance and an exceptional employee experience across the lifecycle.

This hands-on role collaborates with People Operations, global payroll and external partners to manage enrollments, complex leaves, billing audits, and clear employee communications.

Qualifications

• 4-6+ years of dedicated experience in US benefits administration, plan design, and leave management.
• Deep, practical knowledge of employment and benefit laws (ERISA, ACA, HIPAA, FMLA, COBRA, FLSA) and experience executing non-discrimination testing.
• Experience working with unionized employee populations and understanding of collective bargaining agreements.
• Highly organized with exceptional financial and auditing skills; meticulous when reconciling monthly carrier bills, payroll deductions, and employee census data.
• Proficiency with enterprise HRIS platforms (Workday Benefits Administration) and carrier EDI feeds.
• Ability to breakdown complex medical, financial and regulatory concepts into easy to understand communications.
• Comfortable with ambiguity, proactive in driving process improvements alongside leadership.
• High integrity, discretion, and sound judgment handling confidential material.

Responsibilities

• Own the end to end benefits experience for employees, managing new hire enrollments and status updates.
• Lead day-to-day inquiries and create clear employee communications, benefit booklets, policy guides, and education sessions.
• Lead monthly carrier billing reconciliation and audits with payroll and finance for accuracy.
• Support compliance with federal, state and local regulations (ERISA, ACA, HIPAA, COBRA, FMLA, etc).
• Maintain all plan documents (SPDs, SBC, plan summaries) and lead annual Open Enrollment.
• Assist with leave of absence workflows (FMLA, state paid family leave, STD/LTD, parental leave, ADA accommodations).
• Manage benefit administration workflows and data integrity within HRIS (Workday), auditing carrier integrations.
• Act as a point of contact for brokers, carriers, 401(k) recordkeepers, pension fund contacts, and wellness vendors.
• Analyze program utilization, claims trends, and benchmarking to optimize plans with the Director of People Operations.

Skills

Benefits administration

Regulatory compliance

Auditing & reconciliation

Workday

EDI feeds

Employee communications

Tools

Workday

EDI feeds

Job description

Via is on a mission to create public transportation systems that provide far greater access to jobs, healthcare, and education. Our platform serves as the technology backbone for modern transit networks, transforming antiquated and siloed public transportation systems into smart, data-driven, and efficient digital networks.

As Via’s Senior Benefits Specialist, you will be supporting the strategy, administration and execution of our US and global health, welfare, retirement and wellness programs. This position is focused on optimizing the employee experience across the lifecycle, ensuring regulatory compliance, and supporting the scale of our benefits offerings to support our growing, dynamic team.

This is a hands-on role— we’re a one-team culture, and you’ll be rolling up your sleeves to support across the board, whether it’s executing annual open enrollments, managing complex leave requests, auditing carrier billing, or delivering clear employee communications. Collaborating closely with Via’s broader People Operations team, global payroll, and external partners, you’ll act as a subject matter expert and trusted resource, helping shape a competitive and exceptional benefits experience that aligns with Via’s mission.

What You’ll Do:

• Own the end to end benefits experience for employees, managing new hire enrollments, offboarding workflows, COBRA, life event changes and qualifying status updates.
• Serve as a thought support lead for day-to-day employee benefit inquiries, while creating clear, engaging employee communications, benefit booklets, policy guides, and education sessions.
• Lead monthly carrier billing reconciliation and audits across all plans, partnering with payroll and finance to ensure deduction and invoice accuracy.
• Support compliance with federal, state and local regulations (ERISA, ACA, HIPAA, COBRA, FMLA, SF HCSO, etc) managing required non-discrimination testing, ACA reporting and required annual notice distributions.
• Maintain all plan documents (SPDs, SBC, plan summaries, etc) and lead the project management and execution of annual Open Enrollment, including HRIS system set up, broker liaison, and employee Q & A sessions.
• Assist with the administration of leave of absence workflows (FMLA, state paid family leave, STD/LTD, parental leave, and ADA accommodations) in close coordination with other members of the People and Payroll team.
• Manage benefit administration workflows and data integrity within our HRIS (Workday), auditing carrier integrations (EDI feeds).
• Act as a point of contact for benefits brokers, carriers, 401(k) recordkeepers, pension fund contacts, and wellness vendors, resolving claim escalations.
• Analyze program utilization, claims trends, employee feedback, and market benchmarking to partner with Director of People Operations on continuous plan optimization and cost-containment initiatives.

Who You Are:

• 4-6+ years of dedicated experience in US benefits administration (preferably with self-insured plans), plan design, and leave management in a fast‑paced environment.
• Deep, practical knowledge of employment and benefit laws (ERISA, ACA, HIPAA, FMLA, COBRA, FLSA) and experience executing non-discrimination testing.
• Experience working with unionized employee populations and understanding of collective bargaining agreements.
• Highly organized with exceptional financial and auditing skills; meticulous when reconciling monthly carrier bills, payroll deductions, and employee census data.
• Proven proficiency with enterprise HRIS platforms (experience with Workday Benefits Administration and carrier EDI feeds is a strong plus).
• Ability to breakdown complex medical, financial and regulatory concepts into easy to understand, supportive communications for employees.
• Comfortable with ambiguity, flexible in adapting to changing needs, and proactive in driving process improvements alongside leadership.
• High integrity, discretion, and sound judgment when handling confidential material including medical records, sensitive employee situations, and compliance audits.

Compensation and Benefits:

• Final salary will be determined by the candidate’s experience, knowledge, and skills. Salary reflected does not include equity or variable pay, where applicable
• Salary Range: $80,000-$90,000 per year
• Comprehensive health coverage, with low-cost dental and vision plans
• A 401(k) with a generous company match and vesting
• Fully paid parental leave for new parents, with extended leave options
• Additional benefits (mental health, pet insurance, and other wellness perks)
• 20 days of paid time off (PTO) annually

Ready to join the ride?

Via is an equal opportunity employer.