Leave & People Operations Specialist

Insomnia Cookies

Employee Leave & People Operations Specialist facilitating onboarding and leave administration processes at Insomnia Cookies. Delivering a seamless employee experience during critical life events at a cookie company.

Posted 5/7/2026full-timePhiladelphia • Pennsylvania • 🇺🇸 United StatesJuniorMid-LevelWebsite

About the role

Key responsibilities & impact

Serve as both a primary executor of onboarding processes and a key owner of leave of absence administration.
Ensure smooth transitions for employees entering the organization and provide critical support throughout leave events.
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.
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.
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.
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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

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. 🍪

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

leave of absence administrationHRISI-9 complianceE-Verifybackground check processonboarding processesunemployment claim processingdata validationauditscompliance checks

Soft Skills

attention to detailorganizational skillsprofessionalismempathycommunication skillscustomer-service mindsetability to prioritizeability to manage sensitive situationsproblem-solvingcollaboration