Benefits Analyst - Contract (6 months)

Whatnot•New York, NY

23h•Hybrid

About The Position

Whatnot is the largest livestream shopping platform in North America and Europe to buy, sell, and discover the things you love. Whether it's trading cards, fashion, electronics, or live plants, our sellers are building real businesses across hundreds of categories. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops. As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact. We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business and bring people together through commerce. 💻 Role Benefits Administration Administer medical, dental, vision, retirement, and supplemental benefits across 15+ vendors. Manage U.S. and international new hire enrollments, including manual enrollments for global entities. Support with compliance requirements (e.g., 5500 filings, audits, required notices). Assist with renewals and vendor implementations as well as Open Enrollment for US employees. Leave of Absence & Accommodations Manage end-to-end leave administration for employees globally (FMLA, parental leave, state-specific leaves, international leaves). Coordinate top-up pay and deduction reconciliation with Payroll. Partner with external leave administrators (e.g., Tilt) and carriers. Track and manage workplace accommodations in compliance with policy and local regulations. Serve as the primary point of contact for escalations and sensitive employee cases. Systems, Payroll & Reporting Maintain and troubleshoot Workday benefits configurations in partnership with People Systems team. Perform payroll reconciliations related to leave, deductions, and fringe benefits. Identify discrepancies between plan rules and system configurations; document and resolve gaps. Employee & Cross-Functional Support Provide employees with quick and high-quality support with benefits and leave inquiries, working with internal and external partners as needed. Review invoices to ensure accurate and timely payments to vendors. Contribute to documentation and process improvements to make the employee experience smooth. We offer flexibility to work from home or from one of our global office hubs, and we value in-person time for planning, problem-solving, and connection. Team members in this role must live within commuting distance of our New York, Los Angeles, San Francisco or Seattle hubs.

Requirements

4+ years of experience in employee benefits administration
Experience managing complex leave programs (multi-state and/or international exposure preferred).
Strong working knowledge of U.S. benefits compliance requirements (FMLA, ERISA, ACA).
Experience with Workday.
Ability to reconcile payroll deductions, invoices, and benefits enrollment files.
Strong attention to detail and decision-making abilities.

Responsibilities

Administer medical, dental, vision, retirement, and supplemental benefits across 15+ vendors.
Manage U.S. and international new hire enrollments, including manual enrollments for global entities.
Support with compliance requirements (e.g., 5500 filings, audits, required notices).
Assist with renewals and vendor implementations as well as Open Enrollment for US employees.
Manage end-to-end leave administration for employees globally (FMLA, parental leave, state-specific leaves, international leaves).
Coordinate top-up pay and deduction reconciliation with Payroll.
Partner with external leave administrators (e.g., Tilt) and carriers.
Track and manage workplace accommodations in compliance with policy and local regulations.
Serve as the primary point of contact for escalations and sensitive employee cases.
Maintain and troubleshoot Workday benefits configurations in partnership with People Systems team.
Perform payroll reconciliations related to leave, deductions, and fringe benefits.
Identify discrepancies between plan rules and system configurations; document and resolve gaps.
Provide employees with quick and high-quality support with benefits and leave inquiries, working with internal and external partners as needed.
Review invoices to ensure accurate and timely payments to vendors.
Contribute to documentation and process improvements to make the employee experience smooth.