Benefits Manager

Squarespace, New York, NY

Help the world share their story

Squarespace is seeking an experienced Benefits Manager to scale and ensure peak competitiveness of our benefits & perks. This role with work alongside our Total Rewards 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. Our Total Rewards team is responsible for ensuring our compensation philosophy and benefits offerings are competitive with the market and appropriate for the needs of Squarespace today and into the future.  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 benefits function.

This role reports into our future Head of Total Rewards and is based in our New York headquarters.


  • Lead and execute our global benefit programs, including but not limited to: medical, dental, vision, life, and disability insurance coverage; Flexible Spending Accounts (FSA), commuter benefits, retirement plans, onsite and remote wellness programming, COBRA, paid time off, and legislated leaves of absence
  • Help define and brand Squarespace’s benefits philosophy and develop a strategic roadmap to operationalize all elements of our evergreen programming in partnership with Culture and Engagement team and other People centers of excellence
  • Lead the annual benefit renewal process and recommend go-forward approach taking into consideration feedback from internal stakeholders, market research, and cost analysis
  • Lead all benefit related trainings and discussions with Squarespace employees, including new hires, recruiters, Squarespace’s executive team, etc.
  • Maintain and upkeep benefit information and policies on internal communications resources, and develop new communication materials, strategies and project plans to enhance employees’ understanding of benefits offerings
  • Serve as the lead point of contact for employee inquiries, while developing ways to streamline operational processes and day-to-day inquiries
  • Ensure plan compliance with regulatory filings and updates, notices, ACA mandates, plan audits, non-discrimination testing, and employee benefit files
  • Research competitive benefit trends and best practices and report out on findings to key stakeholders
  • Partner with Finance and Head of Total Rewards on the benefit budget and forecast


  • A minimum of 10 years of benefits experience, with 5 years of managing the function including domestic and international program modeling, design, and implementation, inclusive of tool management for administration and employee support
  • Knowledge of regulatory requirements in the US and international markets
  • Ability to assess and action current programs for compliance
  • Highly organized and self-sufficient with the ability to manage multiple high priorities in a fast-paced environment
  • Highly effective verbal and written communication skills to collaborate, develop partnerships and instill trust of vendors, managers, and employees
  • Highly adaptable and solution-oriented; able to thrive amidst uncertainty and shifting priorities
  • Experience in a high-growth company at a top, employer of choice a plus  


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 900 is headquartered in downtown New York City, with offices in Dublin and Portland. For more information, visit www.squarespace.com/about.


  • 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.

About Squarespace

Squarespace's platform empowers millions of people — from individuals and local artists to entrepreneurs shaping the world’s most iconic businesses — to share their stories and create an impactful, stylish, and easy-to-manage online presence.


Want to learn more about Squarespace? Visit Squarespace's website.