Leave Specialist - REMOTE

Job Description

Manage full cycle leave of absence cases via Service Now for all of the United States plus Canada. The case load average is 150+ cases, and the specialist handles each case from intake to eligibility checks, sending required notices customized by state, reviewing medical certification documents for accuracy, making approval or denial decisions, and providing guidance and support to managers and employees.

The role serves as the primary point of contact for managers and employees throughout the leave of absence process and processes and approves leave transactions in Workday.

The Leave Specialist performs a variety of both routine and complex administrative and professional tasks. The specialist serves as a subject‑matter expert on the leave process as well as state and federal leave laws.

Remote work from home.

• Facilitate the leave of absence process company‑wide, performing individualized leave assessments, resolving issues, and escalating cases as appropriate.
• Monitor work queues and prioritize cases as required while managing extensive phone, e‑mail, and case‑management communications with employees and managers.
• Process and approve leave transactions in Workday (requests, returns, modifications) accurately and quickly.
• Maintain information and documentation in the case‑management system to track and ensure accurate and timely case management.
• Provide counseling and coaching for managers and employees around taking leave, types of leave, and eligibility, as well as modifying leaves to ensure a smooth transition and leave process.

• Identify areas for continuous improvement within internal operations and processes.
• Maintain deep expertise and specialized knowledge of legal and statutory policies around leaves of absence.
• Perform other duties as assigned, including participation in other activities, projects, and growth initiatives within the Compliance or Employee Services area.

• Strong knowledge of federal and state absence laws and regulations.
• Strong organizational and analytical skills.
• Strong written, verbal communication and interpersonal skills.
• Ability to establish and maintain effective working relationships with employees, managers, and HR teams.
• Ability to handle confidential, sensitive, and personal information appropriately.
• Ability to work in a timely and organized manner to meet mandatory deadlines.
• Ability to create and maintain professional relationships at all levels of the organization.
• Flexibility, self‑driven attitude, and the ability to excel in a fast‑paced environment.
• Ability to work independently and as a member of a team.
• Experience with Microsoft Office products (Word, Excel, PowerPoint); familiarity with Workday and/or Service Now is a plus.
• Experience working in case management and HRIS systems (Service Now, Workday, etc.).

• Bachelor’s degree required or equivalent experience in Human Resources or a related field.
• Three (3) years or more in an HR generalist or HR compliance role (e.g., leave of absence, ADA, Employee Relations).
• Three (3) years or more of demonstrated experience facilitating leave of absence processes, including coaching and consulting others.
• Three (3) years or more of experience interpreting and ensuring human resources regulatory compliance.
• One (1) year or more of experience in high‑volume, complex case management.
• Professional in Human Resources (PHR) certification.
• Experience with Microsoft Office products (Word, Excel, PowerPoint); familiarity with Workday and/or Service Now is a plus.
• Experience working in case management and HRIS systems (Service Now, Workday, etc.).

HR Compliance

At Ryder, you’re trusted to make an impact—while enjoying room to grow and having a voice that’s heard. Our culture is built on respect, collaboration, and shared pride in doing great work rooted in innovation and safety.

The compensation offered to a candidate may be influenced by a variety of factors, including relevant experience, education, work location, market data, and internal equity. The position may also be…