Senior Benefits & Leave Analyst

Etsy•Brooklyn, NY

22h•Hybrid

About The Position

We're looking for a Senior Benefits & Leave Analyst who cares deeply about both the details and the people behind them. You'll be a key individual contributor on a small, high-impact team owning benefits and leave work in roughly equal measure, with global scope across the US, Ireland, UK, Canada, India, and Mexico. This is a full-time position reporting to the Senior Manager, Global Benefits. In addition to salary, you will also be eligible for an equity package, an annual performance bonus, and our competitive benefits that support you and your family as part of your total rewards package at Etsy. This role requires your presence in Etsy’s Brooklyn Office once or twice per week depending on your proximity to the office. Candidates living within commutable distance of Etsy’s Brooklyn Office Hub may be the first to be considered. Learn more details about our work modes and workplace safety policies here. Our People + Workplace team exists to make Etsy a place where employees can do the best work of their careers. The Global Benefits team is a small group of people who genuinely care about how employees experience the moments that matter. We manage health, leave, retirement and wellbeing programs across six countries, partnering closely with HR Business Partners, Payroll, Legal, People Systems, Employee Relations and Finance to keep things running and to make our programs better year over year. We're a small team with a big remit, which means everyone gets meaningful work and a real say in how we do it.

Requirements

4+ years in benefits and/or leave, with global exposure and a track record of running defined processes consistently and improving them over time
Hands-on Workday Benefits configuration experience — comfortable with business processes, reporting, troubleshooting, and UAT
Strong understanding of US benefits and leave compliance, including ACA, ERISA, HIPAA, COBRA, FMLA, and state and local leave laws
A customer-service mindset — you treat every employee interaction as a moment that matters, you're adaptable without being reactive, and you always close the loop
Analytical proficiency and clear writing — you can build a clean model in Sheets and write a benefits FAQ an employee actually understands
Sound judgment with sensitive employee data, and the instinct to know when to escalate
Experience supporting QBRs, tracking vendor SLAs, and working across People, Payroll, Legal, and Finance

Nice To Haves

Global benefits experience in the regions we operate in: Ireland, UK, Canada, India, and Mexico
Background supporting benefits in a high-growth technology company
CEBS, CBP, or a similar credential
Spanish language proficiency

Responsibilities

Manage core benefits administration (e.g., open enrollment, leave, COBRA) and compliance filings.
Maintain the compliance calendar and monitor US and international legislative changes (e.g., paid family leave, ACA, retirement).
Optimize and automate process flows, including configuring and improving Workday Benefits business processes, integrations, and reports with People Systems.
Ensure data integrity and visibility using tools like Zendesk, Coupa, and Sheets, and resolve discrepancies in carrier files.
Manage complex and sensitive benefits and leave cases with warmth, clarity, and follow-through.
Improve employee self-service content/intake flows and lead employee wellness programming and education initiatives.
Serve as the day-to-day vendor and broker contact, managing SLAs, utilization/cost trends, QBRs, RFPs, contract renewals, and invoice processing.
Collaborate regularly with cross-functional partners: People Partners, Payroll, Legal, Finance, and People Systems.