Leave & Time Off Specialist

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee employee leave management from the initial request through to their return to work, which includes FMLA, state and local family and medical leave, company-sponsored leaves, parental leave, military leave, bereavement, personal/unpaid leave, and other relevant programs.

• Assess leave eligibility while considering applicable federal, state, local, and company protections.

• Handle notices, certifications, documentation, deadlines, extensions, recertifications, return-to-work requirements, and case closures.

• Manage concurrent or overlapping leave entitlements.

• Maintain communication with employees and managers throughout the leave process.

• Coordinate leave status, pay implications, benefits continuation, timekeeping, and return-to-work requirements in collaboration with Payroll, Benefits, HR, and managers.

• Supervise active leaves and follow up on exhaustion dates, missing documentation, expected returns, and necessary actions.

• Administer accommodation requests and facilitate the ADA interactive process.

• Review supporting documentation confidentially and coordinate the implementation of approved accommodations.

• Research accommodation options and escalate complex, high-risk, or potentially adverse decisions.

• Act as a subject matter expert for PTO, sick leave, and company time-off programs.

• Administer and monitor state and local paid sick leave as well as statutory time-off requirements.

• Collaborate with HRIS to ensure accurate Rippling policies, eligibility rules, accruals, and carryover configurations.

• Resolve time-off inquiries and discrepancies while coordinating corrections with HRIS and Payroll.

• Maintain records, trackers, reports, metrics, and compliance documentation related to leave and accommodations.

• Stay informed on regulatory changes and assist with audits and compliance reviews.

• Enhance and automate workflows, communications, tracking, and reporting using Rippling, AI, and other technologies.

• Develop SOPs, templates, employee resources, manager guidance, and standardized communications.

• Collaborate with Employee Relations, Benefits, Payroll, HRIS, HRBPs, managers, and Legal teams.

• Complete assigned tasks and deliverables punctually and within budget.

• Perform additional related duties as required.

⛳️ Requirements

• Proficient knowledge and hands-on administration of FMLA and multi-state leave regulations.

• Experience in independently managing leave cases from the initial request to the return to work.

• Familiarity with administering ADA workplace accommodations and facilitating the interactive process.

• Capability to evaluate overlapping federal, state, local, and company leave entitlements.

• Experience with administering both intermittent and continuous leaves, as well as tracking leave usage.

• Ability to interpret leave regulations and translate them into practical guidance for employees and managers.

• Experience managing medical certifications, leave documentation, eligibility determinations, deadlines, extensions, return-to-work requirements, and related case documentation.

• Strong judgment regarding when leave or accommodation matters should be escalated.

• Excellent attention to detail, follow-through, and case management capabilities.

• Ability to handle a high-volume caseload while ensuring accuracy and timely communication with employees.

• Capacity to manage sensitive medical and employee information with discretion and confidentiality.

• Knowledge of PTO, paid sick leave, and state/local time-off requirements.

• Experience with HRIS and leave-management systems; familiarity with Rippling is highly preferred.

• Understanding of the interplay between leave, payroll, benefits, timekeeping, and HRIS processes.

• Strong research and analytical skills across various jurisdictions.

• Ability to create reports, trackers, and leave metrics.

• Proficiency in leveraging technology, AI, and automation to enhance administrative processes.

• Strong written and verbal communication skills.

• Ability to work independently in a fast-paced, fully remote environment.

• Bachelor’s degree in human resources, business, or a related field OR a recognized HR certification such as PHR, SPHR, SHRM-CP, or SHRM-SCP OR two years of human resource experience.

• Minimum of five years of direct, hands-on experience in leave and accommodation administration, ideally supporting a multi-state workforce.

• Capability to meet physical demands, including frequently remaining stationary and moving within a home office.

• Willingness to travel up to 10%, potentially to any or all 50 US states.

🏝️ Benefits

• A selection of comprehensive medical plans, including two PPO-style options and an HDHP with HSA choice.

• Flexible spending accounts (FSA).

• Dental and vision coverage.

• Medical, dental, and vision benefits available for spouse/domestic partner and dependent children up to age 26.

• 401(k) plan with company matching and a self-directed brokerage account option.

• Paid time off, including additional leave during the last week of the year.

• Company-paid life insurance for employees and eligible dependents.

• Short- and long-term disability and AD&D coverage.

• Opportunities for professional development.

• Tuition reimbursement support.

• Assistance with professional licensing.

• Paid parental leave available after one year of employment.

• Remote work flexibility from anywhere in the United States.