Senior Benefits Specialist

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.