Benefits Analyst

  • Oakland, CA, USA
  • Employees can work remotely
  • Full-time
  • Alternate Location: San Francisco, United States
  • Position open to remote: Yes
  • Current Square Employee?: Apply via go/jobs with your Square email.

Company Description

Square builds common business tools in unconventional ways so more people can start, run, and grow their businesses. When Square started, it was difficult and expensive (or just plain impossible) for some businesses to take credit cards. Square made credit card payments possible for all by turning a mobile phone into a credit card reader. Since then Square has been building an entire business toolkit of both hardware and software products including Square Capital, Square Terminal, Square Payroll, and more. We’re working to find new and better ways to help businesses succeed on their own terms—and we’re looking for people like you to help shape tomorrow at Square.

Job Description

Square is looking for a Benefits Analyst with global Workday Benefits experience to assist with the daily benefits system support and reporting. This is a full-time remote or Bay Area role reporting to the US Benefits Manager based in the San Francisco area.

You will:

  • Guide communication between the Global Benefits team and Business Systems on Workday requirements, benefit tickets, testing, and issues
  • Work with the Business Systems team to resolve global benefits-related system issues and propose process improvements for benefits administration
  • Manage daily activities around integrations including troubleshooting data, file failures, error handling and general issue resolution
  • Oversee US benefits processing for new hires, terminations, and qualified life events by working with Square's insurance carriers and our benefits tool, Workday
  • Manage US Open Enrollment process in Workday and other OE projects as assigned
  • Maintain employee benefit records with accuracy and confidentiality
  • Responsible for US compliance projects, including ACA, SF HealthCare Ordinance, and Benefits NDT
  • Manage the Workday set up of benefits processes, leave, and time off projects on for new countries
  • Help automate global benefits processes for payroll purposes
  • Support administrators to ensure benefits payroll accuracy
  • Configure, prepare, run and distribute ad hoc data reports through Workday
  • Partner with other team members to deliver new hire benefits sessions
  • Assist team with managing internal communication tools (wiki, emails, and slack)
  • Other benefits-related projects and responsibilities




You have:

  • 3+ years of previous Benefits experience (knowledge of global benefits and leave of absence is a huge plus)
  • 3-5 years of Workday benefits experience (understanding of the Workday global benefits module is a huge plus)
  • Project management experience
  • Knowledge of HR processes, benefits, compliance, and integrated payroll processes
  • Flexible schedule (supporting team in Ireland and the US)

Additional Information

At Square, we value diversity and always treat all employees and job applicants based on merit, qualifications, competence, and talent. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We will consider for employment qualified applicants with criminal histories in a manner consistent with the requirements of the San Francisco Fair Chance Ordinance. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us by sending an email to assistance(at) We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible.


At Square, we want you to be well and thrive. Our global benefits package includes:
  • Healthcare coverage
  • Retirement Plans
  • Employee Stock Purchase Program
  • Wellness perks
  • Paid parental leave
  • Paid time off
  • Learning and Development resources