Associate Director, Leave and Accommodations

Your Opportunity:

Chewy is seeking an Associate Director, Leave and Accommodations based in one of Chewy’s corporate hubs (Plantation, FL, Bellevue, WA, Boston, MA, or Minneapolis, MN). In this role, you will be responsible for the design, policy, vendor management, and compliance of aspects of Absence programs (paid time off, Leaves of Absence (LOA), FMLA, local and state leave requirements, short- and long-term disability, and ADA support). As a key member of the Benefits team, you will lead program design and implementation, collaborate with internal and external partners, and ensure operational efficiency. This role blends strategic oversight with hands-on management and is a fantastic opportunity to demonstrate your skills in thought leadership, critical thinking, and communication – all to enhance the Team Member’s experience!

At Chewy, we offer more than just a job. You’ll join an encouraging culture where your contributions, identity, and career goals matter. We’re committed to helping you grow, earn competitive pay, and find happiness in your work!

What You’ll Do:

• Oversee LOA programs, including paid time off, FMLA, state and local leave requirements, ADA support, and disability programs
• Serve as the policy owner for Leave and Absence/Time Off policies, reviewing and improving current policies for compliance and standard processes
• Maintain compliance with federal, state, and local laws, advise management on required actions, and assess enforcement of policies
• Collaborate with HR and other partners to provide guidance on Absence (LOA) and Time off plans (paid time off, unpaid time off, sick leave, holiday, etc.)
• Analyze data and feedback from employees, HR, and others while leading efforts to improve the employee experience within Disability, Leave, and Accommodation programs
• Manage external vendors to ensure high levels of service for Chewy Team Members and compliance with LOA program requirements, analyzing trends and developing improvement plans where necessary
• Provide coaching to leaders on disability, leaves, and accommodation processes, and develop training for HR and new leaders to maintain compliance and increase understanding
• Support program market evaluations to ensure up-to-date practices are implemented and service gaps are addressed, staying informed about industry trends and benchmark against other organizations
• Lead continuous improvement efforts by interpreting data, including qualitative feedback, to find opportunities for process enhancements
• Develop communication tools and regular reports to ensure partners are informed about program status and updates

What You’ll Need:

• Bachelor’s degree in business, human resources, or a related field
• 8+ years of proven experience in FMLA, LOA, ADA, and PTO programs, including design and management in a large, diverse organization (10K+ employees)
• Leadership experience in LOA administration, including with vendor management
• Ability to lead and implement new and enhanced LOA programs
• Demonstrated knowledge and experience evaluating third-party administrators and in-house versus outsourced leave administration
• Strong communication (oral and written), ability to maintain confidentiality and manage critical information, and the ability to collaborate effectively cross-functional teams
• Expertise in interpreting data, problem-solving, and implementing improvement plans
• Solid knowledge of federal and state laws
• Experience with Workday is a plus
• CPDM and/or CLMS designation preferred
• Limited travel may be required