About DatadogDatadog is a leading monitoring and security platform for cloud applications. Our platform brings together end-to-end traces, metrics, and logs to make applications, infrastructure, and third-party services fully observable. At Datadog, we’re dedicated to creating exceptional employee experiences as we continue to scale globally.

The OpportunityWe are looking for a Leave Specialist to join our People Operations team to support the Americas. You will play a critical role in ensuring seamless, white-glove support for employees navigating the leave of absence process, including Parental, Medical, and other statutory leaves. You’ll act as a trusted resource, collaborating closely with employees, managers, and benefits partners to ensure a smooth and compliant leave experience.

This role is ideal for someone who thrives on organization, has a passion for employee experience, and enjoys working in a dynamic, fast-paced environment.

What You’ll Do

• Serve as the main point of contact for employees across the Americas region (U.S., Canada, and LATAM) regarding leave administration, including Parental Leave, Medical Leave, and other applicable statutory leaves.
• Manage end-to-end leave processes, from initiation to return-to-work, ensuring compliance with country, state, and local regulations.
• Partner with our US Leave Administrator - UNUM
• Partner with Benefits, Payroll, HRBPs, and managers to ensure accurate leave tracking, pay, and handoffs for a smooth employee experience.
• Provide white-glove support to employees by addressing inquiries in a timely and empathetic manner.
• Ensure all leave records are accurately maintained in Workday and aligned with compliance standards.
• Collaborate with legal and compliance teams to stay up-to-date on relevant leave laws, policies, and company requirements.
• Analyze leave trends and provide insights to inform process improvements and enhance the employee experience.
• Support training for managers and HR teams to ensure understanding of leave policies and responsibilities.

Who You Are

• 4+ years of experience in leave administration, benefits coordination, or HR operations, preferably in a global or regional role.
• Strong understanding of U.S. leave laws (FMLA, ADA, etc.) and experience managing leaves in Canada and/or LATAM is a plus.
• Experience working with HRIS systems, particularly Workday; familiarity with tools like UNUM is a plus.
• Detail-oriented and organized, with the ability to manage multiple priorities and ensure accurate documentation.
• Exceptional interpersonal and communication skills, with a focus on delivering empathetic, white-glove employee support.
• A proactive problem solver who can identify process improvements and collaborate effectively across teams.
• Ability to adapt and thrive in a dynamic, fast-paced environment.

Why You’ll Love Working at Datadog

• Join a fast-growing company with a culture of innovation and collaboration.
• Work with a passionate, global team that values employee experience and operational excellence.
• Enjoy a hybrid work model based out of our vibrant New York City office.
• Access generous benefits, including comprehensive healthcare, parental leave, wellness programs, and more.
• Be part of a company that cares about your professional growth, offering learning opportunities and career development.

Equal Opportunity EmployerDatadog is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

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