Leave Specialist – Contractor

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

📋 Description

• Act as the main point of contact for employees dealing with leaves of absence, offering prompt, empathetic, and informed assistance.

• Oversee the entire process of employee leaves from initiation to return to work, covering medical, parental, family care, personal, military, and other protected leave types.

• Collaborate closely with our third-party leave administrator (Sparrow) to ensure effective case management, proper documentation, and support for employees.

• Evaluate leave documentation and facilitate subsequent actions while guaranteeing compliance with relevant federal, state, and local regulations.

• Coordinate accommodations and return-to-work processes in collaboration with Employee Relations and People Business Partners, including fitness for duty documentation and necessary workplace accommodations.

• Work alongside Payroll and People Operations to ensure correct pay, benefits, and employment status during each leave period.

• Keep precise records and documentation within Rippling and other internal systems.

• Address inquiries from employees and managers regarding leave policies, eligibility, timelines, and procedures.

• Track active leave cases and proactively manage key milestones, deadlines, and necessary communications.

• Identify areas for improving workflows, documentation, templates, and automations to enhance efficiency and the employee experience.

• Assist with reporting, audits, and compliance tasks related to leave administration.

⛳️ Requirements

• Over 5 years of specialized leave administration experience supporting U.S. employees.

• Proven experience in independently managing comprehensive leave administration for a multi-state employer.

• In-depth understanding of FMLA, ADA, CFRA, PWFA, USERRA, state paid family and medical leave programs, and other relevant leave laws.

• Experience collaborating with third-party leave administrators such as Sparrow, Sedgwick, Lincoln Financial, The Hartford, or similar vendors.

• Strong grasp of the relationship between leave administration, payroll, benefits, and HR operations.

• Excellent organizational skills and attention to detail, with the capability to handle multiple concurrent leave cases.

• Outstanding written and verbal communication skills, demonstrating a high level of empathy and professionalism.

• Ability to exercise sound judgment while managing confidential and sensitive employee information.

• Comfortable working autonomously in a fast-paced, rapidly growing environment.

🏝️ Benefits

• Comprehensive Health Coverage: Medical, dental, and vision insurance, in addition to life and disability coverage.

• Parental Leave & Family Support: Up to 18 weeks of paid leave and a stipend for new child expenses.

• Financial Wellness: 401(k) program and equity opportunities.

• Meals & Home Office Support: Stipends for home office setup and ongoing meal funds, with customized perks for both remote and in-office employees.

• Time Off to Recharge: Flexible PTO, 12 paid holidays, and a full week off during winter break.

• Wellness & Development: Annual stipends for personal and professional growth.

• Mental & Physical Health Support: Free access to therapy through the Grow platform, weekly flexible hours for self-care (“Mental Health Mornings/Afternoons”), and memberships to leading wellness apps (such as One Medical, Headspace, and Talkspace).

• Extra Perks: Discounts on pet insurance, commuter benefits, and global travel assistance.