Senior Benefits Associate

We’re looking for a knowledgeable, service‑oriented Benefits & Leave Programs Specialist to oversee the administration of our employee leave and benefits offerings. This role plays a central part in ensuring employees receive accurate guidance, timely support, and a seamless experience throughout their leave and benefits lifecycle. You’ll collaborate closely with HR, payroll, and external partners to maintain compliance, streamline processes, and enhance employee understanding of available programs.

• Act as the primary point of contact for all leave programs, including FMLA, state and municipal leave laws, paid family leave, and company-sponsored leave options.
• Oversee the end‑to‑end leave process—from intake and documentation to communication, vendor coordination, and return‑to‑work planning.
• Maintain strict adherence to federal, state, and local leave regulations and ensure consistent, compliant administration.

• Manage day‑to‑day operations of health and welfare plans, including medical, dental, vision, life insurance, disability programs, and retirement offerings.
• Review and process employee benefit elections, changes, and terminations within Workday.
• Partner with payroll and compensation teams to ensure accurate and timely benefit deductions.
• Lead weekly benefits orientations for new hires and support ongoing employee education initiatives.
• Assist with annual benefits renewal, open enrollment activities, and rollout of new programs.
• Support wellness and well‑being initiatives across the organization.
• Process monthly vendor invoices and employee reimbursements.

• Ensure all required federal and state filings, notices, and disclosures are completed accurately and on schedule (e.g., ERISA, EEOC, ACA, Medicare Part D, CMS, PCORI, 1094/1095‑C, MA HIRD, San Francisco Health Ordinance).
• Respond to ad hoc reporting needs, benchmarking requests, and special projects.

• Provide timely, professional responses to employee and HR inquiries regarding benefits, leave, and related policies.
• Build strong working relationships with internal teams and external vendors to support a positive employee experience.

• Strong relationship‑building abilities with both internal stakeholders and external partners.
• Exceptional attention to detail and clear, polished communication skills.
• Highly motivated, collaborative, and comfortable working in a fast‑paced environment.
• Proven ability to manage multiple priorities and maintain confidentiality.
• Resourceful, proactive, and solutions‑driven in daily work and long‑term initiatives.

• At least five years of experience in benefits administration and/or leave management.
• Solid understanding of benefits compliance requirements and leave regulations.
• Experience in financial services is a plus.
• Advanced proficiency in Excel, PowerPoint, and Word.