We are seeking an experienced and highly skilled Sr. Leave & Benefits Specialist to serve as a subject matter expert in employee leave programs and North America benefits administration. This senior role will oversee complex leave cases, drive process improvements, support compliance efforts, and provide advanced guidance to employees, HR business partners, and leaders. The ideal candidate will have an in-depth understanding of federal and state leave laws, health insurance practices, and strong analytical, communication, and interpersonal skills. A commitment to delivering compassionate, accurate, and efficient support to employees during their leave or benefits-related situations is essential to success in this role. This is a hybrid role, working three days a week at the Orlando office and two days a week at home.

This is a Hybrid position working 3 days a week out of our Orlando HUB Office.

Key Responsibilities

• Oversee the coordination and monitoring of all employee leaves of absence and workplace accommodation requests, including the review of complex cases, audits, escalations, approvals, denials, and return-to-work plans.
• Manage the administration of all leave programs, including FMLA, Short-Term and Long-Term Disability, state-specific leaves, company leave programs, ADA/ADAAA accommodations.
• Prepare, review, and deliver detailed reporting and analytics on employee leave trends to HR leadership, HR Business Partners, HRIS, and managers.
• Provide direction to Payroll weekly on leave status, PAFs, and timesheet updates to ensure accurate and timely processing.
• Oversee the maintenance, accuracy, and audit readiness of leave of absence records across HR systems, including Lincoln Financial, People Portal and UKG.
• Act as a primary point of contact for employee leave-related inquiries via email, dedicated Leave phone line for calls and text, and ticketing system.
• Communicate leave policies, eligibility requirements, and procedural guidance, providing advanced interpretation and support to employees and leaders.
• Deliver timely and comprehensive responses while ensuring proper follow-up and case resolution.
• Act as a liaison between employees, HR leadership, and Lincoln case managers to support efficient case handling and resolve escalations.
• Identify, develop, and implement opportunities to streamline and enhance leave administration workflows, documentation practices, and benefits invoicing procedures.
• Recommend and support the rollout of updated or new leave-related policies, ensuring alignment with compliance standards and organizational goals.
• Collaborate with cross-functional partners (HR, Payroll, Benefits, Legal) to strengthen process integration and consistency.
• Analyze trends, recurring issues, and system needs to recommend enhancements, including HRIS and vendor platform improvements.
• Lead or participate in audits, internal reviews, and compliance initiatives to ensure accuracy and adherence to regulatory requirements.
• Partner closely with the Sr. Benefits and Compensation Manager on complex benefits administration tasks, vendor coordination, and strategic initiatives.
• Participate in cross-training to deepen subject matter knowledge of broader HR functions.
• Serve as a skilled backup for the Compensation Analyst, supporting monthly Go Bonus calculations and approvals, advanced data entry, and reporting.
• Assist with annual benefits Open Enrollment, yearly plan reviews, audits, and other enterprise-level projects.
• Manage and serve as the point of contact for our annual North America Wellbeing Week across all locations.
• Ensure accuracy, compliance, and proper documentation across all benefits and compensation processes.
• Support annual Length of Service program across North America.
• Assist in review, document processing and payments for our Tuition Reimbursement program.

Qualifications and Experience

• Bachelor’s degree in Human Resources, Business Administration, or a related field required.
• 4+ years of experience in leave administration, benefits, or a related HR support role.
• Advanced working knowledge of FMLA, ADA/ADAAA, state-specific leave laws, and other applicable federal and local regulations.
• Comfortable speaking to employees about complex leave matters mainly on the phone or via text/email daily.
• Strong familiarity with benefits programs, including medical, dental, vision, life insurance, disability plans, and vendor partnerships.
• Experience with HRIS systems (e.g., UKG, Workday, or similar); experience working with leave vendor platforms (e.g., Lincoln, Benefits Express) preferred.
• HR certification (SHRM-CP/SCP, PHR/SPHR, CEBS, or related) preferred but not required.
• Strong analytical and problem-solving skills with the ability to manage and prioritize multiple complex tasks in a fast-paced environment.
• Excellent written and verbal communication skills, including the ability to convey complex policies and decisions in a clear, employee-friendly manner.
• High degree of professionalism, discretion, and confidentiality when handling sensitive employee information.
• Proficiency in Microsoft Office Suite, particularly Excel, with demonstrated experience generating and analyzing reports.
• Commitment to delivering high-quality, empathetic support to employees navigating leave or benefits matters.

Excellent Health Care Options: Comprehensive medical, dental, and vision coverage.
Paid Time Off (PTO).
Merlin Magic Pass: Free entry for friends and family to our amazing parks & attractions.
Recognition Programs and Rewards.
401(k) Program: Save for the future with company matching contributions.
Tuition Reimbursement Programs: Get support for further education and career growth.
Numerous Learning and Advancement Opportunities: Grow your skills and advance your career with us!