Employee Benefits Specialist

Benefits & Wellness Specialist Location: Fully Remote (U.S.) – Preference for Boston-based candidates Hours: 40 hours/week Compensation: $35-$40/Hour About the Opportunity We’re seeking a highly skilled Benefits & Wellness Specialist to support a global financial organization’s benefits and wellness programs across the Americas. This individual will play a key role in managing day-to-day benefits operations, optimizing processes, and providing consultative support to employees on all aspects of benefits — from healthcare and retirement to wellness and work-life programs. The ideal candidate is a savvy, hands-on benefits professional with exceptional technical and communication skills, who thrives in a dynamic, fast-paced, and collaborative environment. Key Responsibilities • Manage end-to-end benefits operations, including onboarding, terminations, and benefits billing/invoicing. • Serve as a primary point of contact for employee benefits inquiries, providing concierge-level service and consultative guidance. • Support HRIS and SharePoint updates related to benefits data and processes. • Assist with leaves of absence, disability, and accommodation processes, ensuring compliance with state and federal laws. • Develop and deliver benefits communications, marketing materials, and policy documentation. • Partner with Finance and Payroll teams to analyze and reconcile benefits data, ensuring accuracy and budget alignment. • Drive operational efficiencies and enhance governance frameworks for benefits programs. • Support compliance activities such as 5500 filings, 1095 reporting, and nondiscrimination testing. • Collaborate with vendors and brokers to ensure exceptional service delivery. • Contribute to system implementations, integrations, and benefits plan consolidations following mergers or acquisitions. Required Qualifications • 5–10+ years of experience as a Benefits Specialist/Analyst in a mid-to-large, multi-faceted organization. • Expertise across healthcare, retirement, wellness, and other corporate benefit programs. • Advanced Excel skills (pivot tables, VLOOKUPs, data analysis). • Strong HRIS experience (Workday strongly preferred). • Bachelor’s degree in Human Resources, Business, Finance, or a related field. • Exceptional communication and interpersonal skills with a service-oriented approach. • Proven experience managing multiple vendors (e.g., 40+ benefits vendors). • Experience supporting benefits integrations or system implementations. • Strong data management, organization, and project management skills. Nice to Have • Workday (highly preferred) • Experience with Cigna, United Healthcare, and ADP • Prior involvement in RFP processes and working with census files • Experience in the financial services or private equity industry Ideal Candidate Profile This role is best suited for a detail-oriented, technically proficient Benefits professional who enjoys both strategic projects and hands-on operational work. You’ll be trusted to manage multiple priorities, partner with internal stakeholders, and provide thoughtful, proactive support to employees across multiple regions.