Leave of Absence Benefits Administrator (Remote)

Location: Remote (Able to attend meetings PST/EST)

Payrate: $40–50/hr (Weekly pay + medical benefits)

Duration: 4-month contract (Excellent potential for extension)

Hours: Full-time: M–F

***Please note: This role requires recent experience with main job duties in supporting Leave of Absence.

Our client is a thriving educational tech company that envisions a world where anyone, anywhere can transform their life by accessing the world’s best learning experience. Their mission and vision unite their team; above all, they share a common passion for ambitious goals. They are also a strong, fun-loving community that shares meals, music, volunteering, sports, and more!

The People team is dedicated to building high-performing teams and delivering a world-class employee experience. As a Benefits Contractor – Leave & Compliance, you will play a critical role in supporting US and Canada leave of absence (LOA) programs and ensuring compliance with key benefits regulations (AAP, ACA, VETS, ERISA). You will be responsible for hands-on management of leave administration, including medical, parental, and statutory leaves, while ensuring processes are compliant and employee-centered. Additionally, you will provide critical compliance support, partnering with internal teams and vendors to prepare audits, filings, and required documentation. This position is ideal for someone detail-oriented, knowledgeable about benefits compliance, and experienced in managing leave programs in both the US and Canada.

Key Responsibilities

Leave of Absence (LOA) Administration

• Manage day-to-day administration of employee leave of absence requests (medical, parental, statutory, and personal) for the US and Canada.
• Partner closely with employees, managers, and People Business Partners to resolve unique and complex leave situations.
• Collaborate with Larkin (leave administration vendor) to ensure accurate case management, compliance with regulations, and timely employee communications.
• Provide Tier 2 support for escalated LOA inquiries, ensuring responses are clear, empathetic, and compliant.
• Maintain documentation and ensure accurate reporting of LOA activity in Workday and ServiceNow (ticketing system).

Compliance & Reporting

• Support ongoing benefits compliance initiatives, including AAP, ACA, VETS, and ERISA reporting and wrap-up requirements.
• Partner with Legal, Payroll, and external vendors to ensure accurate data collection and timely submissions.
• Assist with benefits audits, government filings, and compliance reporting for the US and Canada.
• Document and maintain compliance processes, ensuring best practices are standardized and repeatable.

Cross-Functional Collaboration

• Work closely with Larkin, People Business Partners, managers, and Payroll to deliver a seamless leave of absence experience.
• Partner with Legal and vendors to ensure compliance with all applicable leave and benefits laws.
• Support rollout of compliance-related process improvements and leave administration initiatives.

Basic Qualifications

• 4+ years of experience in Benefits Administration, with 70–80% of duties focused specifically on Leave of Absence management.
• Experience managing LOA programs and compliance in the US; Canadian statutory leave experience preferred.
• Strong employee-facing experience with clear and empathetic communication.
• Skilled at working with managers, business partners, and maintaining strong cross-functional relationships.
• Experience handling complex leave cases, including difficult conversations with empathy and professionalism.
• Clear communicator able to explain complex policies to employees, managers, and cross-functional partners.
• Experience providing Tier 2 support for escalated LOA inquiries.
• Compliance knowledge: Strong understanding of US benefits regulations (ACA, ERISA, AAP, VETS) and some Canadian statutory leave requirements.
• Systems expertise: Proficient in Workday HCM (benefits and LOA modules) and experience with ticketing systems such as ServiceNow or similar.
• Problem solver: Adept at navigating complex leave cases and compliance issues, ensuring solutions are compliant and employee-friendly.

Bonus Qualifications

• Experience working in a fast-paced tech or growth-stage company.
• Hands-on experience with compliance reporting tools and vendor portals.
• Prior experience supporting audits, ERISA wrap reporting, or ACA filings.

TCWGlobal is an equal opportunity employer. We do not discriminate based on age, ethnicity, gender, nationality, religious belief, or sexual orientation.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.