Benefits Manager in New York, NY

$150K - $200K(Ladders Estimates)

Squarespace   •  

New York, NY 10001

Industry: Consumer Technology


11 - 15 years

Posted 56 days ago

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

Valid Through: 2019-10-17