At Insomnia Cookies, our people are the secret ingredient to our late-night magic. We’re looking for an Employee Leave & People Operations Specialist to join our People Team and play a key role in delivering a seamless employee experience from hire through critical life events. This role blends onboarding execution with ownership of leave of absence administration, ensuring employees are supported with accuracy, care, and compliance. If you’re detail-oriented, people-focused, and enjoy balancing operations with employee support, we’d love to meet you!

What You’ll Do

As the Leave & People Operations Specialist, you’ll serve as both a primary executor of onboarding processes and a key owner of leave of absence administration. You’ll ensure smooth transitions for employees entering the organization and provide critical support throughout leave events.

Leave of Absence & Compliance Owner

Administer and manage the full lifecycle of leave of absence cases, ensuring compliance with federal, state, and local regulations.

Serve as a primary point of contact for employees and managers regarding leave processes, policies, and expectations.

Partner with third-party administrators, where applicable, to ensure a seamless leave experience.

Maintain accurate records, documentation, and timely communications related to all leave cases.

Provide administrative and case management support for complex or escalated leave situations.

Onboarding Owner

Process new hires in HRIS (Currently UKG) to ensure accurate and timely setup.

Maintain I-9 compliance through E-Verify, including case management and reverifications.

Audit new hire offer letters to ensure accuracy and compliance.

Manage the background check process for the U.S. and Canada, including required communications.

Troubleshoot onboarding system issues to ensure a smooth hiring experience.

People Team Support & Employee Experience

Triage and respond to employee inquiries through the People Team ticketing system (FreshDesk), escalating as needed.

Provide timely, accurate, and empathetic support across HR topics, with a strong focus on leave and onboarding questions.

Support unemployment claim processing and documentation.

Assist with employee data requests, audits, and government reporting.

Process Improvement & Operational Support

Identify opportunities to improve onboarding and leave processes for efficiency and employee experience.

Maintain and enhance knowledge base documentation and response templates.

Support data validation efforts, including audits and compliance checks.

Partner with cross-functional teams to improve HR systems and workflows.

What We’re Looking For

2–4 years of HR or People Operations experience.

Hands-on experience with leave of absence administration and compliance required.

Experience with onboarding, employee support, or HR operations preferred.

Familiarity with unemployment processes and general HR administration.

Experience with Workday preferred.

Strong attention to detail and organizational skills.

Ability to manage sensitive situations with professionalism and empathy.

Strong communication skills with a customer-service mindset.

Comfortable working in HR systems, ticketing tools, and LMS platforms.

Ability to prioritize and manage a high volume of requests in a fast-paced environment.

Why You’ll Love Working Here

At Insomnia Cookies, we’re more than late-night treats—we’re a community. As part of our team, you’ll enjoy:

A fun, inclusive, and people-first culture.

Opportunities to grow your HR career and expand your skillset.

A role with meaningful impact on employee experience, especially during critical life events.

Hands-on experience across onboarding and leave administration.

And of course… warm, delicious cookies. 🍪