Payroll and Benefits Specialist

Squarespace is seeking a talented Payroll & Benefits Specialist  to work alongside our Payroll & Benefits team and the rest of the People team.


Our People Team’s mission is simple: create an environment where people can do their life’s best work. The Payroll & Benefits Team is responsible for building programs and processes that ensure seamless support of our ever growing organization.  Our benefits and perks provide holistic wellness and peace of mind so that our employees can concentrate on what they do best.  As the next member of our team, your work will be integral to supporting our mission.  You are ambitious and ready to take on the challenge of building a world-class Payroll & Benefits function.


This role reports into our Manager of Wellness & Experience and is based in our New York headquarters.


  • Maintain data integrity of our HRIS for all employees (New York City, Portland, and Dublin)
  • Assist our Payroll & Benefits Lead with the accurate processing of payroll, internal and external audits, payroll tracking, and system configuration updates
  • Onboard new US based employees: maintain (electronic) employee files, provide guidance on I-9 and W-4 requirements, and lead the Payroll & Benefits section of new hire orientation
  • Process changes due to qualifying life events and terminations, manage the annual Open Enrollment process, and liaise between Squarespace’s various benefit vendors
  • Research creative and competitive benefits/perks to add to our existing program
  • Coordinate quarterly wellness events, such as flu shots or health fairs
  • Ensure accuracy and consistent updating of the payroll, benefits, and time off sections of company intranet
  • Act as a trusted resource for current and former employees on all payroll and benefits matters, including requests for employment verifications, unemployment claims, FMLA, and other personal leaves of absence
  • Active involvement with other Wellness & Experience team projects, as needed


  • 1-3 years of payroll and benefits experience
  • Previous experience with UltiPro is a plus
  • Detail oriented and able to handle various tasks with overlapping deadlines
  • Strong analytical capability; advanced proficiency with Microsoft Excel and/or Google Sheets
  • Exudes credibility, professionalism, and warmth when providing guidance and support to employees
  • Highly adaptable and solution-oriented; able to thrive amidst uncertainty and shifting  priorities
  • Bachelor’s degree in HR or a related field preferred


 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 570 is headquartered in downtown New York City, with offices in Dublin and Portland. For more information, visit


  • Health insurance with 100% premium covered
  • Flexible vacation & paid time off
  • Equity plan
  • 401(k) plan with employer match
  • Free lunch and snacks
  • Dog-friendly workplace
  • And more

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.


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