Benefits Analyst - Contract (6 months)

Whatnot, Inc.

Job Overview

Location

New York, NY

Job Type

Full-time

Full Job Description

📋 Description

• As a Benefits Analyst at Whatnot, you will play a critical role in supporting the company’s rapid growth by ensuring seamless administration of employee benefits and leave programs across U.S. and global teams, directly contributing to employee well-being and organizational compliance in a fast-moving, innovative live commerce environment.
• You will administer medical, dental, vision, retirement, and supplemental benefits across 15+ vendors, manage U.S. and international new hire enrollments—including manual processes for global entities—and support compliance with federal requirements such as 5500 filings, audits, and mandated notices, while assisting with benefits renewals, vendor implementations, and annual Open Enrollment cycles.
• You will manage end-to-end leave of absence administration for employees worldwide, covering FMLA, parental leave, state-specific leaves, and international leave types, coordinate top-up pay and deduction reconciliation with Payroll, partner with external administrators like Tilt and insurance carriers, track and manage workplace accommodations in line with policy and local regulations, and serve as the primary escalation point for sensitive or complex employee cases.
• You will maintain and troubleshoot Workday benefits configurations in collaboration with the People Systems team, perform payroll reconciliations tied to leave, deductions, and fringe benefits, identify and resolve discrepancies between plan rules and system setups, and ensure accurate invoice review and timely vendor payments.
• You will provide responsive, high-quality support to employees on benefits and leave inquiries, liaising with internal and external partners as needed, contribute to process documentation and continuous improvements to enhance the employee experience, and operate with flexibility to work remotely or from Whatnot’s hubs in New York, Los Angeles, San Francisco, or Seattle, with an expectation of periodic in-person collaboration.
• You will join a mission-driven, fast-paced culture where curiosity, bias toward action, and outcome-focused thinking are valued, gaining deep expertise in global benefits administration, Workday systems, and compliance while making tangible impact on employee experience during a pivotal stage of Whatnot’s growth as a leader in live commerce.
• This role offers the opportunity to develop specialized skills in managing complex, multi-jurisdictional leave programs, strengthen your technical proficiency in benefits platforms like Workday, and build cross-functional influence by partnering with Payroll, People Systems, Legal, and HR teams to drive process excellence and compliance.

🎯 Requirements

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

🏖️ Benefits

• Flexibility to work remotely or from Whatnot’s global office hubs in New York, Los Angeles, San Francisco, or Seattle
• Opportunity to work with a diverse, mission-driven team shaping the future of live commerce
• Exposure to global benefits administration and compliance across multiple jurisdictions
• Hands-on experience with Workday and benefits vendor management
• Professional growth in a fast-scaling, innovative startup recognized as a top employer
• Supportive culture that values curiosity, action, and impact over hierarchy or credit

Skills & Technologies

Remote

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Whatnot, Inc.

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About Whatnot, Inc.

Whatnot operates a live-stream marketplace for collectibles, sneakers, trading cards, apparel, and other hobby items. Sellers host real-time auctions and fixed-price shows while buyers bid or purchase through the mobile app. The platform combines live video, integrated payments, and authenticated shipping to reduce fraud. Founded in 2019, the company is headquartered in Los Angeles and has raised multiple venture rounds to expand categories and international markets.

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