Senior Benefits Associate

  • Location
    Boston, Massachusetts
  • Contract Type
    Permanent
  • Posted
  • Start Date
    2026-04-27
  • Salary
    USD90000 - USD100000 per annum
  • Expiry Date
    2026-04-06

Benefits & Leave Programs Specialist

Overview

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.

Core Responsibilities

Leave of Absence Management

  • 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.

Benefits 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.

Compliance & Reporting

  • 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.

Employee Support

  • 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.

Qualifications

Professional Skills

  • 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.

Experience & Education

  • Bachelor’s degree required.
  • 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.
  • Familiarity with Workday is preferred.

The SR Group (US), Inc. is acting as an Employment Agency in relation to this vacancy.

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