Associate Director Leave and Accommodation Programs

Chewy • Plantation, FL

3d • $137,500 - $221,500 • Hybrid

About The Position

Chewy is seeking an Associate Director of Leave and Accommodations Programs based in one of Chewy’s corporate hubs (Plantation, FL, Bellevue, WA, or Boston, MA)! In this role, you will be responsible for the strategy, design, governance, vendor management, and compliance of aspects of Absence programs including 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 complex cross-functional programs and initiatives from concept through implementation, driving operational excellence, process optimization and improvement. You will partner closely with HR, Legal, Payroll, Technology, Finance, Procurement, and leaders across the business, while overseeing external vendor relationships and leading critical initiatives such as vendor evaluations, RFPs, and program transformations. This role blends strategic leadership with hands-on execution and offers an exciting opportunity to build the Team Member experience through innovative program design, effective change management, and efficiently scalable solutions. 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!

Requirements

• Bachelor’s degree in business, human resources, or a related field
• 8+ years of demonstrable experience in FMLA, LOA, ADA, and PTO programs, including design and management in a large, diverse organization (10K+ employees)
• Deep expertise in FMLA, ADA, disability programs, federal, state, and local leave requirements, and leave administration protocols
• Strong project and program management skills, including experience managing multiple business leaders and large-scale and cross-functional projects with complex workstreams and dependencies, from strategy through implementation
• Experience leading vendor evaluations, RFP processes, implementation efforts, and ongoing vendor governance
• Proven experience managing third-party administrators and driving accountability through performance metrics, service-level agreements, and continuous improvement initiatives
• Strong change management experience, including leader engagement, communication planning, training, and adoption support
• Demonstrated success driving process optimization, operational excellence, and scalable solutions through data-driven decision making
• Exceptional communication, presentation, and relationship-building skills, with the ability to influence leaders at all levels of the organization
• Strong analytical and problem-solving skills with experience using data to develop recommendations and drive outcomes

Nice To Haves

• Experience with Workday preferred
• CPDM and/or CLMS designation preferred
• Limited travel may be required

Responsibilities

• Own the strategy, governance, and administration of Leave of Absence, disability, accommodation, and paid time off programs, ensuring alignment with strategic objectives and Team Member needs
• Act as policy owner for Leave and Absence and Time Off policies, enhancing practices to maintain compliance, consistency, and operational effectiveness
• Maintain compliance, advise management on required actions, and assess enforcement of policies
• Lead the design, implementation, enhancement, and ongoing management of LOA programs, ensuring scalable and sustainable solutions
• Serve as the program lead for complex initiatives, developing project plans, managing timelines, identifying risks and dependencies, and driving successful execution across multiple workstreams
• Partner cross-functionally to create and implement program improvements and critical initiatives
• Lead vendor strategy and governance activities, including vendor evaluations, Requests for Proposal (RFPs), implementation planning, contract support, performance management, and ongoing relationship management
• Evaluate third-party administrator performance through service-level agreements, metrics, and internal feedback, developing action plans to address gaps and improve outcomes
• Lead change management and ongoing improvement efforts associated with scalability, policy updates, process enhancements, technology implementations, and vendor transitions, ensuring effective communication, engagement, education, and adoption
• Conduct market evaluations and review program data (operational metrics, trends, and feedback) to find opportunities for process optimization, automation, improved service delivery, competitive differentiation, and enhanced Team Member experiences
• Develop executive-ready reporting, dashboards, and communications to offer a clear view of program performance, trends, risks, and opportunities
• Provide guidance and coaching to HR partners and business leaders on leave, disability, accommodation, and time-off programs, ensuring consistent application of policies and practices
• Stay informed on industry trends, emerging regulations, and market practices, using external benchmarking and insights to inform program strategy and recommendations

Benefits

• 401k
• new hire and annual equity grant
• annual bonus
• medical/Rx insurance
• vision insurance
• dental insurance
• life insurance
• disability insurance
• hospital indemnity insurance
• critical illness insurance
• accident insurance
• parental leave
• family services benefits
• backup dependent care
• flexible spending accounts
• telemedicine
• pet adoption reimbursement
• employee assistance program
• discounts including 10% off pet insurance and 20% off at Chewy.com
• unlimited PTO, subject to manager approval
• six paid holidays per year
• paid sick and family leave in compliance with applicable state and local regulations

What This Job Offers

• Job Type: Full-time
• Career Level: Manager