Leave & Benefits Specialist

Locations: US-WI-Milwaukee | US-IL-Chicago | US-TX-Dallas

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The Leave & Benefits Specialist is a key member of the HR Benefits team, responsible for delivering a high-quality employee benefits experience through the administration of health and welfare programs and the management of leave of absence and disability processes. This role oversees the end-to-end coordination of leave cases, ensuring compliance with federal, state, and local regulations, and serves as a primary resource for employees, HR, and leadership on benefits and leave matters.

The position partners closely with vendors, Payroll, Accounting, and HR to ensure data accuracy, seamless operations, and timely issue resolution. In addition, the role supports employee engagement through EAP programming and wellness initiatives and contributes to a positive employee experience. This role also plays a key role in evaluating and enhancing leave and benefits processes, driving continuous improvement through technology, automation, and manager enablement.

Leave of Absence & Disability Administration

• Serve as subject matter expert and primary administrator for all leave of absence and salary replacement programs while on leave, including FMLA, applicable state and local leave programs, and firm-specific leaves (personal, military, bereavement), as well as short-term disability, paid parental leave, PTO, and vacation. Advise employees, HR, and leadership on eligibility, policy interpretation, and process.
• Manage leave cases end-to-end, from initial request through return-to-work/closure, including eligibility determination, documentation review, designation, and ongoing case tracking in accordance with federal, state, and local regulations.
• Administer leave programs in compliance with applicable laws and firm policies, ensuring timely issuance of required notices, accurate recordkeeping, and consistent application of leave and pay practices.
• Act as primary liaison with third‑party leave and disability vendors, monitoring case activity, resolving escalations, and ensuring timely and accurate communication and claim processing. Escalate issues to the Benefits Manager or Sr Manager, Benefits & Compensation as necessary.
• Coordinate leave‑related impacts across employee relations, payroll, benefits, and operations, including pay calculations, benefits continuation, premium handling, and billable hour considerations, partnering closely with Payroll, Accounting, and HR.
• Monitor regulatory developments and assess impact to leave programs, contributing to policy updates, process enhancements, and compliance initiatives. Work with HR and General Counsel’s office to implement changes to processes and procedures as needed.

Benefits Administration & Employee Support

• Deliver day‑to‑day administration of health and welfare benefit programs, including enrollments, life event changes, and eligibility management, ensuring accuracy across HRIS, payroll, and vendor systems.
• Respond to and resolve complex employee inquiries, including claims, eligibility, and coverage issues, acting as an advocate and coordinating with vendors to ensure timely resolution.
• Coordinate and deliver EAP‑related programming, including scheduling, promoting, and supporting webinars, educational sessions, and awareness initiatives to drive utilization and employee engagement.
• Lead wellness initiatives for the local office, planning and executing programs that promote employee well‑being, engagement, and alignment with broader firm wellness strategy.
• Serve as liaison with benefits carriers and administrators, tracking issues, escalating service concerns, and…