• Location
    • New York
  • Date Posted
  • May. 26, 2021
  • Function
  • HR
  • Sector
  • Business Applications

Squarespace’s Total Rewards team is seeking a Benefits Specialist who has a passion to learn all things benefits while providing administration and support for all employee benefit plans, programs, and policies. In this role, you will manage employee benefit inquiries, execute our benefit programs, manage compliance related needs, monitor benefit eligibility, and 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 and provides flexibility for our employees.


  • Responsible for the administration of employee benefit programs including medical, dental, vision; life insurance plans, disability programs, accommodation requests and leaves of absence, and 401(k)
  • Responsible for participating in vendor management activities including day to day oversight, regular status calls and 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 and facilitate compliance related matters, in partnership with external vendors, including (but not limited to) completion of Form 5500s, ACA filings, annual audits, and 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 and 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, and Finance on renewals, benefit program implementations and 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 and state regulations, filing and compliance requirements affecting employee benefits programs, including ERISA, COBRA, ACA, etc.
  • Excellent presentation, writing, and analytical skills
  • Technical proficiency in one or more HR Information Systems

About squarespace

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

Benefits & Perks

  • Health insurance with 100% premium covered for you and 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 and adoption benefits
  • Free lunch and snacks at all offices
  • Education reimbursement
  • Dog-friendly workplace in New York office
  • Commuter benefit in the form of reduced tax (Ireland) and pretax (US)

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and 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.