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Squarespace // creative tools for designing websites
New York City    Posted: Thursday, June 10, 2021
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Squarespace's Total Rewards team is seeking a Benefits Specialist who has a passion to learn all things benefits while providing administration & support for all employee benefit plans, programs, & policies. In this role, you will manage employee benefit inquiries, execute our benefit programs, manage compliance related needs, monitor benefit eligibility, & support all other ad-hoc projects. 

You will report to our Global Benefits Manager in our NYC headquarters.

All Squarespace employees are working remotely at this time. We are closely monitoring the status of COVID-19 as we continue our work to build a return-to-work plan that ensures a safe return to our offices & provides flexibility for our employees. 


  • Responsible for the administration of employee benefit programs including medical, dental, vision; life insurance plans, disability programs, accommodation requests & leaves of absence, & 401(k) 
  • Responsible for participating in vendor management activities including day to day oversight, regular status calls & process improvement initiatives
  • Act as liaison to employees on in support of benefit questions, helping to bring resolution to benefits matters 
  • Conducting new hire benefits orientation 
  • Manage reconciliation of all benefit invoices managing against budgets to ensure accuracy
  • Coordinate & facilitate compliance related matters, in partnership with external vendors, including (but not limited to) completion of Form 5500s, ACA filings, annual audits, & non-discrimination testing 
  • Support the annual benefits Open Enrollment process, including working with vendors/brokers consultants to manage employee communications, prepare benefit plan materials, coordinate timelines & address employee questions
  • Gather feedback from employees on benefit programs to provide insights to Global Benefits Manager on potential opportunities to enhance benefit program offerings
  • Partner with internal stakeholders such as Payroll, People Operations, HR Business Partners, Recruiting, Legal, & Finance on renewals, benefit program implementations & other areas related to benefits administration
  • Perform other Benefits/HR ad hoc projects as needed


  • 2+ years of experience working in Benefits Administration 
  • Knowledge of federal & state regulations, filing & compliance requirements affecting employee benefits programs, including ERISA, COBRA, ACA, etc.
  • Excellent presentation, writing, & analytical skills
  • Technical proficiency in one or more HR Information Systems


Squarespace makes beautiful products to help people with creative ideas succeed. By blending elegant design & sophisticated engineering, we empower millions of people from individuals & local artists to entrepreneurs shaping the worlds most iconic businesses to share their stories with the world. Squarespaces team of more than 1,200 is headquartered in downtown New York City, with offices in Dublin & Portland. For more information, visit

Benefits & Perks

  • Health insurance with 100% premium covered for you & your dependent children
  • Flexible vacation & paid time off
  • Up to 20 weeks of paid family leave
  • Equity plan for all employees
  • Retirement benefits with employer match
  • Fertility & adoption benefits
  • Free lunch & snacks at all offices
  • Education reimbursement
  • Dog-friendly workplace in New York office
  • Commuter benefit in the form of reduced tax (Ireland) & pretax (US)

Today, more than a million people around the globe use Squarespace to share different perspectives & experiences with the world. Not only do we embrace & celebrate the diversity of our customer base, but we also strive for the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender, gender identity or expression, or veteran status. We are proud to be an equal opportunity workplace.

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